Compound and method for producing same

Abstract

To provide a novel production method of a compound for obtaining an organic silicon compound by forming a carbon-silicon bond using a raw material high in versatility.SOLUTION: A production method of a compound includes a reaction process of reacting a compound represented by formula (10) with a compound represented by formula (9) in the presence of a catalyst to obtain a compound represented by formula (1) or (1') where the catalyst is a compound of gold carried by a metal oxide, a metal oxo acid salt, or carbon. In the formulae, n10 is an integer of 1, or more, R11 and R12 are hydrocarbon groups which may have H or a substituent, Z11 is a hydrocarbon group which may have a substituent, X11 is a leaving group, R91 is an alkyl group, an aryl group or the like, n11 and n12 are an integer of 1 or more, and n11+n12=n10 (≥2).SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a compound and a method for producing the same. [Background technology]

[0002] Among organic compounds, organosilicon compounds containing carbon-silicon (C-Si) bonds are useful as raw materials or intermediates for pharmaceuticals and agricultural chemicals, as well as functional materials and their raw materials or intermediates. Therefore, methods for forming carbon-silicon bonds have been actively investigated.

[0003] Well-known conventional methods for forming carbon-silicon bonds include a method in which a halosilane such as a chlorosilane is used with an organometallic compound to carry out a nucleophilic substitution reaction to form a carbon-silicon bond; a method in which a hydrosilane is used with an alkene to carry out a hydrosilylation reaction in the presence of a metal catalyst such as platinum or rhodium to form a carbon-silicon bond; and a method in which a silyl coupling reaction is used with a silyl metal and an alkyl halide in the presence of a metal catalyst to form a carbon-silicon bond.

[0004] However, these methods have problems. For example, the organometallic compounds, alkenes, and alkyl halides are usually produced from alcohols through multi-step reactions, and some of these reactions are carried out under special conditions. Therefore, these raw materials tend to be expensive and difficult to obtain. Furthermore, many of these raw materials are unstable and difficult to handle. Among them, organometallic compounds are highly dangerous. Furthermore, the silylmetals that are the target of the alkyl halides' reaction are also highly dangerous and expensive. Therefore, if carbon-silicon bonds could be formed using other raw materials that can be produced from alcohols, this method could be more useful.

[0005] Disclosed methods using such other raw materials include a method of forming a carbon-silicon bond by reacting a fluorosulfonic acid alkyl ester with silylborane in the presence of a copper catalyst (see Non-Patent Document 1), and a method of forming a carbon-silicon bond by reacting a fluorosulfonic acid alkyl ester with silyllithium (see Non-Patent Document 2). Fluorosulfonic acid alkyl esters are a type of ester, highly versatile, and can be obtained by the esterification reaction of alcohol, with the advantage that they can be produced relatively easily from alcohol. In these reactions, the carbon-oxygen (CO) bond in the fluorosulfonic acid alkyl ester is cleaved, and a new carbon-silicon (C-Si) bond is formed. [Prior art documents] [Non-patent literature]

[0006] [Non-Patent Document 1] M. Oestreich et al., Synlett 2016, 27, 1274-1276. [Non-patent document 2] A. Studer et al., Org. Lett. 2020, 22, 6568-6572. Summary of the Invention [Problem to be solved by the invention]

[0007] However, the fluorosulfonic acid alkyl esters used in the methods described in Non-Patent Documents 1 and 2 have the problem of being unstable and difficult to handle. Furthermore, there are only a few types of silylboranes, which are the reaction targets, and silyllithiums have the problem of being flammable and unstable. Therefore, there is a need for the development of a new method for forming carbon-silicon bonds using versatile raw materials such as esters.

[0008] The present invention aims to provide a novel method for producing a compound, which produces an organosilicon compound by forming a carbon-silicon bond using a highly versatile raw material, and to provide a novel compound by the method. [Means for solving the problem]

[0009] The present invention employs the following configuration. [1]. The following general formula (10)

[0010] [ka] (In the formula, n 10 is an integer greater than or equal to 1; R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 10 If is 2 or more, n 10 R 11 may be the same or different, and n 10 R 12 may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11 When is the hydrocarbon group which may have a substituent, Z 11 and R 11 may be bonded to each other to form a ring; X 11 is represented by the following general formula (101):

[0011] [ka] (In the formula, R 13 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group; a bond marked with an * is X 11is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102):

[0012] [ka] (In the formula, R 14 is an alkyl group, an aryl group, or an aralkyl group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which n is bonded. 10 If is 2 or more, n 10 X's 11 may be the same or different from each other.) and a compound represented by The following general formula (9)

[0013] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (1):

[0014] [ka] (In the formula, n 10 , R 11 , R 12 , Z 11 and R 91 is the same as above, and n 10 If is 2 or more, n 10 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other.

[0015] [ka] (In the formula, n 11 and n 12 are each independently an integer of 1 or more, provided that n 11 +n 12 =n 10 (≥2); n 10 , R 11 , R 12 , Z 11 , X 11 and R 91 is the same as above; n 11 If is 2 or more, n 11 R 11 may be the same or different, and n 11 R 12 may be the same or different, and n 11 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; n 12 If is 2 or more, n 12 R 11 may be the same or different, and n 12 R 12 may be the same or different, and n 12 X's 11 may be the same or different from each other, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [2]. The following general formula (20)

[0016] [ka] (In the formula, Z 21 is a hydrocarbon group which may have a substituent, and a carbon atom in the hydrocarbon group may be substituted with a nitrogen atom together with a hydrogen atom bonded to the carbon atom, and The following general formula (9)

[0017] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (2):

[0018] [ka] (In the formula, Z 21 and R 91 is the same as above. The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [3]. The following general formula (30)

[0019] [ka] (wherein l1 is an integer of 2 or more; l2 is 0 or 1; R 31 is an alkylene group, one or more methylene groups in the alkylene group may be substituted with an arylene group, and 11 R 31 may be the same or different from each other; R 32 is an alkylene group or an arylene group, and when l2 is 1, l1 R 32 may be the same or different from each other; wherein the terminal carboxy group may form a salt, and The following general formula (9)

[0020] [ka] (In the formula, R91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (3):

[0021] [ka] (In the formula, R 31 and R 91 is the same as above. The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [4]. The following general formula (40)

[0022] [ka] (In the formula, R 41 and R 42 are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and R 41 and R 42 When both are the alkyl groups, R 41 and R 42 may be bonded to each other to form a ring; R 43 is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group; R 44 is an alkyl group, an aryl group, or an aralkyl group; The following general formula (9)

[0023] [ka] (In the formula, R 91is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (4):

[0024] [ka] (In the formula, R 41 , R 42 , R 43 and R 91 is the same as above. The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [5]. The following general formula (50)

[0025] [ka] (In the formula, R 51 is a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; R 52 is an alkyl group, an aryl group, or an aralkyl group; The following general formula (9)

[0026] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (5):

[0027] [ka] (In the formula, R 51 and R 91 is the same as above. The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [6]. The following general formula (10)-1

[0028] [ka] (In the formula, R 111 and R 121 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 111 and R 121 at least one of is a hydrogen atom; Z 111 represents an alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 111 When is the alkyl group having 1 to 7 carbon atoms, Z 111 and R 111 may be bonded to each other to form a ring; X 111 is represented by the following general formula (101)-1

[0029] [ka] (In the formula, R 131represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X 111 is formed with respect to the carbon atom to which the following is bonded.)

[0030] [ka] (In the formula, R 141 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 111 is formed with respect to the carbon atom to which is bonded.) or a bromine atom. The following general formula (9)-1

[0031] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (1-1)

[0032] [ka] (In the formula, R 111 , R 121 , Z 111 and R 911 is the same as above. The method for producing a compound according to [1], wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [7]. The following general formula (10-2)

[0033] [ka] (In the formula, R 112 and R 122 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 112 and R 122 At least one of R is a hydrogen atom, and two R 112 may be the same or different, and two R 122 may be the same or different from each other; Z 112 represents an alkylene group, alkenylene group, or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 112 When is the alkyl group having 1 to 7 carbon atoms, Z 112 and R 112 may be bonded to each other to form a ring; X 112 is represented by the following general formula (101)-2

[0034] [ka] (In the formula, R 132 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X 112 is formed with respect to the carbon atom to which the following is bonded.)

[0035] [ka] (In the formula, R 142 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 112 is formed with respect to the carbon atom to which is bonded.) or a bromine atom. The following general formula (9)-1

[0036] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (1)-2

[0037] [ka] (In the formula, R 112 , R 122 , Z 112 and R 911 is the same as above. The method for producing a compound according to [1], wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [8].The following general formula (20)-1

[0038] [ka] (wherein m1 is an integer of 1 to 5; R 211 and R 212are each independently a hydrogen atom, an alkyl group of 1 to 7 carbon atoms which may have a substituent, an alkenyl group of 2 to 7 carbon atoms which may have a substituent, or an aryl group of 6 to 10 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group of 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group of 1 to 3 carbon atoms, an acyloxy group of 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group, and when m1 is 2 or more, 211 may be the same or different, and m R 212 may be the same or different, and R 211 and R 212 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 211 and R 212 may be bonded to each other to form a ring, m1 is 2 or more, and R 211 Comrades or R 212 When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R 211 R 212 may be bonded to each other to form a ring, and R 211 and R 212 When either or both of R 211 and R 212 may be replaced with a nitrogen atom, together with the hydrogen atom attached to said carbon atom; m2 is 0 or 1; R 213 and R 214each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 213 and R 214 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 213 and R 214 may be bonded to each other to form a ring, The following general formula (9)-1

[0039] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (2)-1

[0040] [ka] (In the formula, m1, m2, R 211 , R 212 , R 213 , R 214 and R 911 is the same as above. [2] The method for producing a compound according to 2, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon. [9].The following general formula (30)-1

[0041] [ka] (In the formula, l 11 is an integer greater than or equal to 2; l 21 is 0 or 1; R 311 is an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group; 11 R 311 may be the same or different from each other; R 321 is an alkylene group having 2 to 6 carbon atoms or an arylene group having 6 to 12 carbon atoms, 21 If is 1, then l 11 R 321 may be the same or different from each other; wherein the terminal carboxy group may form a salt, and The following general formula (9)-1

[0042] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (3)-1

[0043] [ka] (In the formula, R 311 and R 911 is the same as above. The method for producing a compound according to [3], wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[10] .The following general formula (40)-1

[0044] [ka] (In the formula, R 411 and R 421 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and R 411 and R 421 When both are the alkyl groups, R 411 and R 421 may be bonded to each other to form a ring; R 431 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms; R 441 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, The following general formula (9)-1

[0045] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (4)-1

[0046] [ka] (In the formula, R 411, R 421 , R 431 and R 911 is the same as above. The method for producing a compound according to [4], wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[11] .The following general formula (50)-1

[0047] [ka] (In the formula, R 511 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; R 521 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, The following general formula (9)-1

[0048] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) and a compound represented by in the presence of a catalyst to form a compound represented by the following general formula (5)-1

[0049] [ka] (In the formula, R 511 and R 911 is the same as above. The method for producing a compound according to [5], wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[12] . The method for producing the compound according to any one of [1] to

[11] , wherein after the reaction step, the catalyst used in the reaction step is recovered, and the recovered catalyst is used to carry out the reaction step again, and a re-reaction step is carried out one or more times.

[13] The method for producing a compound according to any one of [1] to

[12] , wherein the catalyst is a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetroxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon.

[14] . The following general formula (1)

[0050] [ka] (In the formula, n 10 is an integer greater than or equal to 1; R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 10 If is 2 or more, n 10 R 11 may be the same or different, and n 10 R 12 may be the same or different from each other; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and is represented by the general formula "-SiR 91 Three R's in "3" 91 may be the same or different, and n 10 If is 2 or more, n 10 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11When is the hydrocarbon group which may have a substituent, Z 11 and R 11 may be bonded to each other to form a ring) (provided that the compound represented by the following formula

[0051] [ka] excluding compounds represented by the formula:

[15] . The following general formula (1')

[0052] [ka] (In the formula, n 11 and n 12 are each independently an integer of 1 or greater; R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 11 If is 2 or more, n 11 R 11 may be the same or different, and n 11 R 12 may be the same or different, and n 12 If is 2 or more, n 12 R 11 may be the same or different, and n 12 R 12 may be the same or different from each other; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and is represented by the general formula "-SiR 91 Three R's in "3" 91 may be the same or different, and n 11 If is 2 or more, n 11 The general formula -SiR 91The groups represented by "3" may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11 When is the hydrocarbon group which may have a substituent, Z 11 and R 11 may be bonded to each other to form a ring; X 11 is represented by the following general formula (101):

[0053] [ka] (In the formula, R 13 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102):

[0054] [ka] (In the formula, R 14 is an alkyl group, an aryl group, or an aralkyl group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which n is bonded. 12 If is 2 or more, n 12 X's 11 may be the same or different.

[16] . The following general formula (2)

[0055] [ka] (In the formula, Z 21 represents a hydrocarbon group which may have a substituent, and a carbon atom in the hydrocarbon group may be substituted with a nitrogen atom together with a hydrogen atom bonded to the carbon atom; R 91is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different.

[17] . The following general formula (4)

[0056] [ka] (In the formula, R 41 and R 42 are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and R 41 and R 42 When both are the alkyl groups, R 41 and R 42 may be bonded to each other to form a ring; R 43 is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and three R 91 may be the same or different. [Effects of the Invention]

[0057] According to the present invention, there is provided a novel method for producing a compound, which uses a highly versatile raw material to form a carbon-silicon bond to obtain an organosilicon compound, and further, the production method provides a novel compound. DETAILED DESCRIPTION OF THE INVENTION

[0058] In this specification, the following abbreviations for functional groups may be used. Me: Methyl group (-CH3) tBu: tert-butyl group (-C(CH3)3) Ph: Phenyl group (-C6H5)

[0059] In this specification, the concentration unit "M" means "mol / L." In this specification, an alkylene group having two or more carbon atoms may be considered to have two or more methylene groups (-CH2-).

[0060] In this specification, when a compound is represented by a general formula or other formula (a non-generalized formula, sometimes simply referred to as a "formula" in this specification), a name with a symbol attached may be given to the general formula or other formula. In such cases, the compound may be given a name with the symbol attached. For example, a compound represented by the general formula (1) described below may be referred to as "compound (1)" in this specification.

[0061] ◎Method of manufacturing compounds <<Manufacturing method (1)>> A method for producing a compound according to one embodiment of the present invention (sometimes referred to herein as "production method (1)") comprises reacting a compound represented by the following general formula (10):

[0062] [ka] (In the formula, n 10 is an integer greater than or equal to 1; R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 10 If is 2 or more, n 10 R 11 may be the same or different, and n 10 R 12 may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11 When is the hydrocarbon group which may have a substituent, Z11 and R 11 may be bonded to each other to form a ring; X 11 is represented by the following general formula (101):

[0063] [ka] (In the formula, R 13 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102):

[0064] [ka] (In the formula, R 14 is an alkyl group, an aryl group, or an aralkyl group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which n is bonded. 10 If is 2 or more, n 10 X's 11 may be the same or different from each other.) (sometimes referred to as "compound (10)" in this specification), The following general formula (9)

[0065] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) (sometimes referred to as "compound (9)" in this specification), in the presence of a catalyst to form a compound represented by the following general formula (1):

[0066] [ka] (In the formula, n 10 , R 11 , R 12 , Z 11 and R 91 is the same as above, and n 10 If is 2 or more, n 10 The general formula -SiR 91 3" may be the same or different from each other.) (in this specification, may be referred to as "compound (1)"), or 10 is an integer of 2 or more, the following general formula (1')

[0067] [ka] (In the formula, n 11 and n 12 are each independently an integer of 1 or more, provided that n 11 +n 12 =n 10 (≥2); n 10 , R 11 , R 12 , Z 11 , X 11 and R 91 is the same as above; n 11 If is 2 or more, n 11 R 11 may be the same or different, and n 11 R 12 may be the same or different, and n 11 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; n 12 If is 2 or more, n 12 R 11 may be the same or different, and n 12 R 12may be the same or different, and n 12 X's 11 may be the same or different from each other.) (sometimes referred to as "compound (1')" in this specification), The catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0068] According to the production method (1), by using the catalyst, the versatile compounds (10) and (9) are used as raw materials to form a carbon-silicon bond, thereby obtaining the compound (1) or compound (1′) as an organosilicon compound.

[0069] <Catalyst> The catalyst is a compound in which gold (Au) is supported on a carrier such as a metal oxide, a metal oxoacid salt, or carbon, and may be any known catalyst.

[0070] Examples of the metal oxide carrier include zirconium oxide (ZrO2), titanium oxide (TiO2), iron trioxide (iron(III) oxide, Fe2O3), iron tetroxide (Fe3O4), aluminum oxide (Al2O3), yttrium oxide (Y2O3), gallium oxide (Ga2O3), and chromium trioxide (chromium(III) oxide, Cr2O3). Examples of the metal oxoacid salt that serves as a carrier include zirconium pyrophosphate (ZrP2O7). The carbon carrier is a material made of carbon or containing carbon as a main component, and specific examples thereof include carbon black, graphite, graphene, carbon nanotubes (CNTs), carbon nanohorns (CNHs), and fullerenes. In this specification, the ratio of the mass of the main component to the total mass of all components is set to 80 mass % or more, not limited to the case of carbon.

[0071] In the catalyst, the gold is preferably in the form of particles. The particle diameter of the particulate gold is preferably 0.5 to 10 nm, and may be, for example, any one of 0.5 to 6.5 nm and 0.5 to 3 nm, any one of 3 to 10 nm and 6 to 10 nm, or 3 to 6.5 nm.

[0072] In the catalyst, the ratio of the mass of gold to the mass of the support (sometimes referred to herein as "gold loading") is preferably 0.1 to 10 mass%, and may be, for example, any of 0.1 to 7 mass%, 0.1 to 4 mass%, and 0.1 to 1 mass%, or any of 3 to 10 mass%, and 6 to 10 mass%, or may be 3 to 7 mass%.

[0073] The catalyst used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0074] The catalyst is preferably a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetroxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon. Use of such a catalyst allows compound (1) or compound (1') to be obtained more easily and in a higher yield. In this specification, a compound in which gold is supported on zirconium oxide may be referred to as a "compound (Au / ZrO2)." This also applies when the support is something other than zirconium oxide.

[0075] The catalyst can be produced by a known method. For example, tetrachloroauric (III) acid and water are mixed, and a base is further added to the resulting mixture to obtain an aqueous solution having a pH of 3.5 to 4.5. A carrier is then added to the aqueous solution, and a base is then added to obtain an aqueous dispersion having a pH of 6.5 to 7.5. Insoluble matter is removed, washed, and dried as necessary. The resulting product is calcined at 280 to 320°C for 0.5 to 5 hours, and the calcined product is then reduced with hydrogen at 180 to 220°C for 0.5 to 5 hours to produce the catalyst. However, this is just one example of a method for producing the catalyst.

[0076] <Compound (10)> The compound (10) is represented by the general formula (10). In the formula, n 10 is the general formula "-CR 11 R 12 X 11 Z of the group represented by 11 is the number of bonds to the n 10 is Z 11 Although it is determined depending on the type of compound (10), it is preferably 1 to 3, and more preferably 1 or 2. Such a compound (10) is easier to produce or obtain.

[0077] In the formula, R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of R is a hydrogen atom. 11 and R 12 are each a hydrogen atom or a combination of a hydrogen atom and the above hydrocarbon group. 11 and R 12 When at least one of the groups is a hydrogen atom, the compound (10) has good reactivity.

[0078] R 11 and R 12The hydrocarbon group in may be linear, branched, or cyclic, and may have both a linear structure (linear or branched) and a cyclic structure. When the hydrocarbon group has a cyclic structure, including when it is cyclic, the cyclic structure may be either an aliphatic hydrocarbon ring (e.g., an aliphatic hydrocarbon group) or an aromatic hydrocarbon ring (e.g., an aromatic hydrocarbon group), and may be either monocyclic or polycyclic. The hydrocarbon group may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

[0079] The hydrocarbon group preferably has 1 to 25 carbon atoms, and may have, for example, any one of 1 to 15, 1 to 12, 1 to 10, 1 to 8, 1 to 6, 1 to 4, and 1 to 2 carbon atoms.

[0080] Preferred examples of the hydrocarbon group include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, and an aralkyl group (arylalkyl group).

[0081] Among the alkyl groups, examples of the chain (straight-chain or branched-chain) alkyl groups include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, a tert-pentyl group, a 1-methylbutyl group, an n-hexyl group, a 2-methylpentyl group, a 3-methylpentyl group, a 2,2-dimethylbutyl group, a 2,3-dimethyl Examples of the alkyl group include linear alkyl groups having 1 to 12 carbon atoms, such as butyl, n-heptyl, 2-methylhexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, 2,4-dimethylpentyl, 3,3-dimethylpentyl, 3-ethylpentyl, 2,2,3-trimethylbutyl, n-octyl, isooctyl, 2-ethylhexyl, nonyl, decyl, undecyl, and dodecyl groups. Among the alkyl groups, examples of the cyclic (monocyclic or polycyclic) alkyl group include cyclic alkyl groups having 3 to 12 carbon atoms, such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, a cyclononyl group, a cyclodecyl group, a norbornyl group, an isobornyl group, a 1-adamantyl group, a 2-adamantyl group, and a tricyclodecyl group.

[0082] Examples of the alkenyl group include monovalent groups having a structure in which one single bond (CC) between carbon atoms in the linear, branched, or cyclic alkyl group is replaced with a double bond (C=C). More specifically, the alkenyl group may be, for example, a chain (linear or branched) alkenyl group having 2 to 12 carbon atoms, such as a vinyl group (ethenyl group, -CH=CH2), an allyl group (2-propenyl group, -CH2-CH=CH2), a 1-propenyl group (2-methylethenyl group, -CH=CH-CH3), an isopropenyl group (1-methylethenyl group, -C(CH3)=CH2), a 1-butenyl group (-CH=CH-CH2-CH3), a 2-butenyl group (-CH2-CH=CH-CH3), or a 3-butenyl group (-CH2-CH2-CH=CH2); a cyclic (monocyclic or polycyclic) alkenyl group having 6 to 12 carbon atoms, such as a cyclohexenyl group or a cyclopentenyl group; Examples include cyclic substituted alkenyl groups having 7 to 20 carbon atoms in which one or more hydrogen atoms in the cyclic alkenyl group are substituted with the chain (straight-chain or branched) or cyclic (monocyclic or polycyclic) alkyl group.

[0083] Examples of the alkynyl group include a monovalent group having a structure in which one single bond (CC) between carbon atoms in the linear, branched, or cyclic alkyl group is replaced with a triple bond (C≡C). More specific examples of the alkynyl group include chain (straight-chain or branched-chain) alkynyl groups having 2 to 12 carbon atoms, such as an ethynyl group (-C≡CH), a 1-propynyl group (-C≡C-CH), a 2-propynyl group (also known as a propargyl group) (-CH-C≡CH), and a 2-nonyn-1-yl group (-CH-C≡C-(CH)CH).

[0084] Examples of the aryl group include a phenyl group (-CH), a 2-methylphenyl group (o-tolyl group), a 3-methylphenyl group (m-tolyl group), a 4-methylphenyl group (p-tolyl group) (-CHCH), a dimethylphenyl group (xylyl group) (-CH(CH)), a 1-naphthyl group, a 2-naphthyl group (-C 10 and monocyclic or polycyclic aryl groups having 6 to 15 carbon atoms, such as groups such as H7).

[0085] Examples of the aralkyl group include monovalent groups having 7 to 27 carbon atoms, such as a benzyl group (phenylmethyl group) and a phenethyl group (phenylethyl group), in which one hydrogen atom in the alkyl group is substituted with the aryl group.

[0086] The hydrocarbon group is more preferably an alkyl group, an alkenyl group, or an aralkyl group, still more preferably an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aralkyl group having 7 to 117 carbon atoms, still more preferably an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and particularly preferably an alkyl group having 1 to 7 carbon atoms.

[0087] R 11 and R 12are each independently preferably a hydrogen atom, an alkyl group, an alkenyl group, or an aralkyl group, more preferably a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 2 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, still more preferably a hydrogen atom, an alkyl group having 1 to 7 carbon atoms, an alkenyl group having 2 to 7 carbon atoms, or an aralkyl group having 7 to 12 carbon atoms, and particularly preferably a hydrogen atom or an alkyl group having 1 to 7 carbon atoms.

[0088] The hydrocarbon group may or may not have a substituent. R 11 and R 12 In this specification, the phrase "a hydrocarbon group may have a substituent" means that one or more hydrogen atoms (-H) in the hydrocarbon group may be substituted with a group (substituent) other than a hydrogen atom, and is not limited to the above cases. Furthermore, unless otherwise specified, the term "group" includes not only an atomic group formed by bonding multiple atoms but also a single atom. When the hydrocarbon group has two or more substituents, these substituents may be the same or different from one another, i.e., all the substituents may be the same, all the substituents may be different, or only some of the substituents may be the same. The bonding position of the substituent in the hydrocarbon group is not particularly limited, and the substituent may be bonded to a terminal carbon atom of the hydrocarbon group or to a non-terminal carbon atom. When the hydrocarbon group has two or more substituents, the multiple (2 to 3) substituents may be bonded to the same carbon atom, or the substituents may be bonded to different carbon atoms.

[0089] Examples of the substituents on the hydrocarbon group include a carboxy group (-C(=O)-OH), a formyl group (-C(=O)-H), a hydroxyl group (-OH), a fluorine atom (-F), a chlorine atom (-Cl), and a bromine atom (-Br).

[0090] n 10 If is 2 or more, n 10R 11 may be the same or different from each other. That is, n 10 R 11 may all be the same, may all be different, or may only be partially the same. n 10 If is 2 or more, n 10 R 12 may be the same or different from each other. That is, n 10 R 12 may all be the same, may all be different, or may only be partially the same.

[0091] In the formula, Z 11 may have a substituent, n 10 is a 2-valent hydrocarbon group. Z 11 The hydrocarbon group in may be linear, branched, or cyclic, and may have both a linear structure (linear or branched) and a cyclic structure. When the hydrocarbon group has a cyclic structure, including when it is cyclic, the cyclic structure may be either an aliphatic hydrocarbon ring (e.g., an aliphatic hydrocarbon group) or an aromatic hydrocarbon ring (e.g., an aromatic hydrocarbon group), and may be either monocyclic or polycyclic. The hydrocarbon group may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

[0092] Z 11 The hydrocarbon group in the formula (I) preferably has 1 to 25 carbon atoms, and may have, for example, any one of 1 to 15, 1 to 12, 1 to 10, 1 to 8, 1 to 6, 1 to 4, and 1 to 2 carbon atoms.

[0093] Z 11 Preferred examples of the hydrocarbon group in the above formula include n-alkyl groups bonded to carbon atoms in hydrocarbons such as alkanes, alkenes, alkadienes, alkatrienes, alkynes, and arenes. 10 n hydrogen atoms have been removed 10Examples of monovalent groups having a structure in which one hydrogen atom bonded to a carbon atom constituting the aromatic ring skeleton of toluene has been removed include a 2-methylphenyl group (o-tolyl group), a 3-methylphenyl group (m-tolyl group), and a 4-methylphenyl group (p-tolyl group) (-CHCH). On the other hand, an example of a monovalent group having a structure in which one hydrogen atom bonded to a carbon atom constituting the methyl group of toluene has been removed is a benzyl group (phenylmethyl group) (-CHCH).

[0094] Z 11 Among the preferred hydrocarbon groups in the above, examples of the monovalent group include an alkyl group, an alkenyl group, an alkynyl group, an aryl group, an aralkyl group (arylalkyl group), and an arylalkenyl group. Z 11 The alkyl group, alkenyl group, alkynyl group, aryl group, and aralkyl group (arylalkyl group) in 11 and R 12 Examples of the alkyl group, alkenyl group, alkynyl group, aryl group, and aralkyl group (arylalkyl group) in Z include the same as those in Z. 11 Examples of the arylalkenyl group in the above formula include groups having a structure in which one hydrogen atom in the alkenyl group is substituted with the above aryl group. Among these, Z 11 The monovalent hydrocarbon group in the formula (I) is more preferably an alkyl group having 3 to 12 carbon atoms, an alkenyl group having 3 to 12 carbon atoms, an alkynyl group having 3 to 12 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, or an arylalkenyl group having 8 to 14 carbon atoms.

[0095] Z 11 Among the preferred divalent hydrocarbon groups in the above, for example, alkylene groups, alkenylene groups, alkynylene groups, arylene groups, aralkylene groups, etc. can be mentioned. Z 11Examples of the alkylene group, alkenylene group, alkynylene group, and arylene group in the above formula (I) include divalent groups having a structure in which one hydrogen atom bonded to a carbon atom having no free valence is removed from the alkyl group, alkenyl group, alkynyl group, and aryl group. 11 Examples of the aralkylene group in the above formula include divalent groups having a structure in which one hydrogen atom bonded to a carbon atom forming an aromatic ring skeleton in the aralkyl group has been removed. Z 11 In the arylene group, the position of the carbon atom having a free valence is not particularly limited. For example, in the case of a phenylene group (—C H —), it may be any of a 1,2-phenylene group, a 1,3-phenylene group, and a 1,4-phenylene group. Among these, Z 11 The divalent hydrocarbon group in the formula (I) is more preferably an alkylene group having 3 to 12 carbon atoms, an alkenylene group having 3 to 12 carbon atoms, an alkynylene group having 3 to 12 carbon atoms, or an arylene group having 6 to 12 carbon atoms.

[0096] Z 11 When the hydrocarbon group in the formula (I) is a group having an unsaturated hydrocarbon ring, the unsaturated hydrocarbon ring may form a coordinate bond with a metal to chelate it.

[0097] Z 11 The hydrocarbon group in the formula (I) may or may not have a substituent. Z 11 When the hydrocarbon group in formula (I) has two or more substituents, these substituents may be the same or different from one another, i.e., all the substituents may be the same, all the substituents may be different, or only some of the substituents may be the same. Z 11 The bonding position of the substituent in the hydrocarbon group in the formula (I) is not particularly limited, and the substituent may be bonded to a terminal carbon atom of the hydrocarbon group or to a non-terminal carbon atom. Z 11When the hydrocarbon group has two or more substituents, the multiple (2 to 3) substituents may be bonded to the same carbon atom, or the substituents may be bonded to different carbon atoms.

[0098] Examples of the substituent on the hydrocarbon group include a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0099] Examples of the alkenyl group having 2 to 6 carbon atoms in the substituent include R 11 and R 12 Among the alkenyl groups in the above, those having 2 to 6 carbon atoms are exemplified. Examples of the fluorinated alkyl group having 1 to 3 carbon atoms in the substituent include groups having a structure in which one or more hydrogen atoms in a methyl group, an ethyl group, an n-propyl group, or an isopropyl group are substituted with fluorine atoms, and may be, for example, a monofluoroalkyl group or a perfluoroalkyl group. Examples of the chlorinated alkyl group having 1 to 3 carbon atoms in the substituent include groups having a structure in which one or more hydrogen atoms in a methyl group, an ethyl group, an n-propyl group, or an isopropyl group are substituted with chlorine atoms, and may be, for example, a monochloroalkyl group or a perchloroalkyl group. Examples of the acyloxy group having 2 to 4 carbon atoms in the substituent include a monovalent group having a structure in which an oxygen atom is bonded to the carbon atom constituting the carbonyl group in an acyloxy group having 2 to 4 carbon atoms, such as an acetyl group (CHCO-), a propionyl group (CHCHCO-), a butyryl group (CH(CH)CO-), or an isobutyryl group ((CH)CHCO-).

[0100] R 11 When is the hydrocarbon group which may have a substituent, Z 11 and R11 are mutually connected to each other, and these (Z 11 and R 11 ) may form a ring together with the carbon atom to which it is attached.

[0101] Z 11 R 11 The bonding position with may be, for example, a terminal carbon atom or a non-terminal carbon atom. Similarly, R 11 Z 11 The bonding position with may be, for example, a terminal carbon atom or a non-terminal carbon atom.

[0102] Z 11 and R 11 The number of bonds in may be 1 or 2 or more. 11 and R 11 The ring formed by may be either monocyclic or polycyclic. Z 11 and R 11 If the number of bonds is 2 or more, Z 11 and R 11 The ring formed by Z is polycyclic. 11 and R 11 If the number of bonds in is 1, then Z 11 and R 11 The ring formed by Z can be either monocyclic or polycyclic. 11 and R 11 is a combination of an alkyl group and an aralkyl group, and the ring formed by the mutual bonding of the carbon atoms in the alkyl group and the carbon atoms constituting the aromatic ring skeleton in the aralkyl group is bicyclic.

[0103] Z 11 and R 11 The number of ring members (the number of atoms constituting the ring skeleton) of the ring formed by is not particularly limited as long as it is 3 or more, and is preferably 5 to 10.

[0104] Z 11 and R 11The ring formed by may be, for example, either a saturated aliphatic ring or an unsaturated aliphatic ring whose ring skeleton is made up of only carbon atoms, or an aromatic ring (aromatic hydrocarbon ring). For example, Z 11 and R 11 are all unsaturated hydrocarbon groups such as alkenyl groups, these unsaturated hydrocarbon groups may be bonded to each other to form an aromatic hydrocarbon ring together with the carbon atoms to which these unsaturated hydrocarbon groups are bonded.

[0105] Z 11 is preferably an alkyl group having 3 to 12 carbon atoms which may have a substituent, an alkenyl group having 3 to 12 carbon atoms which may have a substituent, an alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, and the substituent is preferably one or more selected from the group consisting of a fluorine atom, a chlorine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0106] In the formula, X 11 is a leaving group in compound (10), which is a group represented by general formula (101) above, a group represented by general formula (102) above, or a bromine atom. The bond marked with a symbol * in the general formula (101) and the bond marked with a symbol * in the general formula (102) are both X 11 The carbon atom to which R is attached (more specifically, 11 , R 12 and Z 11 is formed relative to the carbon atom to which it is bonded.

[0107] R 13is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group. R 13 The alkyl group, aryl group and aralkyl group in R 11 and R 12 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above.

[0108] R 13 Examples of the alkoxy group in 11 and R 12 and monovalent groups having a structure in which the alkyl group is bonded to an oxygen atom. R 13 Examples of the chain (linear or branched) alkoxy group in the formula (I) include a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, a tert-butoxy group, an n-pentyloxy group, an isopentyloxy group, a neopentyloxy group, a tert-pentyloxy group, a 1-methylbutyloxy group, an n-hexyloxy group, a 2-methylpentyloxy group, a 3-methylpentyloxy group, a 2,2-dimethylbutyloxy group, a 2,3-dimethylbutyloxy group, an n-hexyloxy group, a 2,3-dimethylbutyloxy group, a 2,4-dimethylbutyloxy group, a 2,5-dimethylbutyloxy group, a 2,6-dimethylbutyloxy group, a 2,7-dimethylbutyloxy group, a 2,8-dimethylbutyloxy group, a 2,9-dimethylbutyloxy group, a 2,10-dimethylbutyloxy group, a 2,11-dimethylbutyloxy group, a 2,12-dimethylbutyloxy group, a 2,13-dimethylbutyloxy group, a 2,14-dimethylbutyloxy group, a 2,15-dimethylbutyloxy group, a 2,16-dimethylbutyloxy group, a 2,17-dimethylbutyloxy group, a 2,18-dimethylbutyloxy group, a 2,19-dimethylbutyloxy group, a 2,20-dimethylbutyloxy group, a 2,21-dimethylbutyloxy group, a 2,22-dimethylbutyloxy group, a 2,23-dimethylbutyloxy group, a 2,24-dimethylbutyloxy group, a 2,25-dimethylbutyloxy group, a 2,26-dimethylbutyloxy group, a 2,27-dimethylbutyloxy group, a 2,28-dimethylbutyloxy group, a 2,29-dimethylbutyloxy group, a 2,30-dimethylbutyloxy group, a 2,3 Examples of such alkyl groups include linear alkoxy groups having 1 to 12 carbon atoms, such as butyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 2,2-dimethylpentyloxy, 2,3-dimethylpentyloxy, 2,4-dimethylpentyloxy, 3,3-dimethylpentyloxy, 3-ethylpentyloxy, 2,2,3-trimethylbutyloxy, n-octyloxy, isooctyloxy, 2-ethylhexyloxy, nonyloxy, decyloxy, undecyloxy, and dodecyloxy. R 13Examples of the cyclic (monocyclic or polycyclic) alkoxy group in the formula (I) include cyclic alkoxy groups having 3 to 12 carbon atoms, such as a cyclopropyloxy group, cyclobutyloxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group, cyclooctyloxy group, cyclononyloxy group, cyclodecyloxy group, norbornyloxy group, isobornyloxy group, 1-adamantyloxy group, 2-adamantyloxy group, and tricyclodecyloxy group. R 13 Examples of the alkoxy group having a cyclic structure in the above include cyclic substituted alkoxy groups having 4 to 24 carbon atoms in which one or more hydrogen atoms in the cyclic alkoxy group are substituted with the chain (straight-chain or branched-chain) or cyclic (monocyclic or polycyclic) alkyl group described above.

[0109] R 13 Examples of the aryloxy group in 11 and R 12 and monovalent groups having a structure in which the aryl group in the above formula is bonded to an oxygen atom. R 13 Examples of the aryloxy group in the formula (I) include monocyclic or polycyclic aryloxy groups having 6 to 15 carbon atoms, such as a phenoxy group, a 2-methylphenoxy group (o-tolyloxy group), a 3-methylphenoxy group (m-tolyloxy group), a 4-methylphenoxy group (p-tolyloxy group), a dimethylphenoxy group (xylyloxy group), a 1-naphthyloxy group, and a 2-naphthyloxy group.

[0110] R 13 Examples of the aralkyloxy group in R include a benzyloxy group (phenylmethyloxy group) and a phenethyloxy group (phenylethyloxy group). 11 and R 12 and monovalent groups having a structure in which the aralkyl group in the formula (I) is bonded to an oxygen atom. R 13 The aralkyloxy group in the formula (I) may have 7 to 27 carbon atoms, for example.

[0111] R 13 The dialkylamino group in the formula (I) is, for example, a group in which two hydrogen atoms in the amino group (—NH) are 11 and R 12 Examples of the monovalent group include a group having a structure substituted with the alkyl group shown in the above formula. R 13 In the dialkylamino group in the formula (I), the two alkyl groups may be the same as each other (an example of such a dialkylamino group is a dimethylamino group) or may be different from each other (an example of such a dialkylamino group is an ethylmethylamino group). R 13 The dialkylamino group in the formula (I) may have 2 to 24 carbon atoms, for example.

[0112] R 13 is preferably an alkyl group having 1 to 12 carbon atoms, an alkoxy group having 1 to 12 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, an aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms.

[0113] R 14 is an alkyl group, an aryl group, or an aralkyl group. R 14 The alkyl group, aryl group and aralkyl group in R 13 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above. R 14 is preferably an alkyl group or an aryl group, more preferably an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms.

[0114] n 10 If is 2 or more, n 10 X's 11 may be the same or different from each other. That is, n 10 X's 11may all be the same, may all be different, or may only be partially the same.

[0115] An example of a preferred compound (10) is a compound represented by the following general formula (10)-1

[0116] [ka] (In the formula, R 111 and R 121 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 111 and R 121 at least one of is a hydrogen atom; Z 111 represents an alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 111 When is the alkyl group having 1 to 7 carbon atoms, Z 111 and R 111 may be bonded to each other to form a ring; X 111 is represented by the following general formula (101)-1

[0117] [ka] (In the formula, R 131 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X111 is formed with respect to the carbon atom to which the following is bonded.)

[0118] [ka] (In the formula, R 141 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 111 is formed with respect to the carbon atom to which is bonded.) or a bromine atom.) (sometimes referred to as "compound (10)-1" in this specification).

[0119] In the formula, R 111 and R 121 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R 111 and R 121 The alkyl group having 1 to 7 carbon atoms in R 11 and R 12 It is the same as the alkyl group having 1 to 7 carbon atoms in the above. However, R bonded to the same carbon atom 111 and R 121 At least one of R is a hydrogen atom. 111 and R 121 are all hydrogen atoms or a combination of a hydrogen atom and the alkyl group having 1 to 7 carbon atoms. 111 and R 121 When at least one of the groups is a hydrogen atom, the compound (10)-1 has good reactivity.

[0120] In the formula, Z 111 represents an alkyl group, alkenyl group or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, and these are 11in the above, it is the same as the alkyl group having 3 to 12 carbon atoms which may have a substituent, the alkenyl group having 3 to 12 carbon atoms which may have a substituent, the alkynyl group having 3 to 12 carbon atoms which may have a substituent, the aryl group having 6 to 12 carbon atoms which may have a substituent, the aralkyl group having 7 to 13 carbon atoms which may have a substituent, or the arylalkenyl group having 8 to 14 carbon atoms which may have a substituent. Z 111 The alkenyl group having 2 to 6 carbon atoms, the fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms as the substituent in Z 11 These groups are the same as the alkenyl group having 2 to 6 carbon atoms, the fluorinated alkyl group having 1 to 3 carbon atoms, the chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms as the substituents in the above formula (I). The alkyl group, alkenyl group, and alkynyl group having 3 to 12 carbon atoms, the aryl group having 6 to 12 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, and the arylalkenyl group having 8 to 14 carbon atoms may have, as a substituent, one or more substituents selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0121] R 111 When is the alkyl group having 1 to 7 carbon atoms, Z 111 and R 111 are mutually bonded to each other, and these (Z 111 and R 111 ) may form a ring together with the carbon atom to which it is bonded. 111 and R 111 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring.

[0122] In the formula, X 111is the general formula (101)-1, the general formula (102)-1, or a bromine atom. The bond marked with a symbol * in general formula (101)-1 and the bond marked with a symbol * in general formula (102)-1 are both X 111 The carbon atom to which R is attached (more specifically, 111 , R 121 and Z 111 is formed relative to the carbon atom to which it is bonded.

[0123] In the formula, R 131 is an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms, and these are R 13 in the above, which is the same as the alkyl group having 1 to 12 carbon atoms, the alkoxy group having 1 to 12 carbon atoms, the aryl group having 6 to 10 carbon atoms, the aryloxy group having 6 to 10 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, the aralkyloxy group having 7 to 13 carbon atoms, or the dialkylamino group having 2 to 4 carbon atoms.

[0124] In the formula, R 141 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms, and these are R 14 In the above, it is the same as the alkyl group having 1 to 12 carbon atoms or the aryl group having 6 to 10 carbon atoms.

[0125] Other examples of preferred compounds (10) include compounds represented by the following general formula (10)-2

[0126] [ka] (In the formula, R 112 and R 122 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 112 and R 122 At least one of R is a hydrogen atom, and two R 112may be the same or different, and two R 122 may be the same or different from each other; Z 112 represents an alkylene group, alkenylene group, or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 112 When is the alkyl group having 1 to 7 carbon atoms, Z 112 and R 112 may be bonded to each other to form a ring; X 112 is represented by the following general formula (101)-2

[0127] [ka] (In the formula, R 132 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X 112 is formed with respect to the carbon atom to which the following is bonded.)

[0128] [ka] (In the formula, R 142 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 112 is formed with respect to the carbon atom to which the bond is made. ) or a bromine atom. ) (sometimes referred to as "compound (10)-2" in this specification).

[0129] In the formula, R 112 and R 122 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, and R 112 and R 122 The alkyl group having 1 to 7 carbon atoms in the general formula (10-1) is R 111 and R 121 The alkyl group has the same structure as the alkyl group having 1 to 7 carbon atoms. However, R bonded to the same carbon atom 112 and R 122 At least one of the R is a hydrogen atom. 112 and R 122 are all hydrogen atoms or a combination of a hydrogen atom and the alkyl group having 1 to 7 carbon atoms. 112 and R 122 When at least one of the groups is a hydrogen atom, the compound (10)-2 has good reactivity. 2 R's 112 may be the same or different, and two R 122 may be the same or different from each other.

[0130] In the formula, Z 112 represents an alkylene group, alkenylene group or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent. Z 112 Examples of the alkylene group having 3 to 12 carbon atoms in 111 Examples of such a divalent group include a divalent group having a structure in which one hydrogen atom has been removed from the alkyl group having 3 to 12 carbon atoms. Z 112 Examples of the alkenylene group having 3 to 12 carbon atoms in 111 Examples of the alkenyl group include a divalent group having a structure in which one hydrogen atom has been removed from the alkenyl group having 3 to 12 carbon atoms in the above formula. Z 112 Examples of the alkynylene group having 3 to 12 carbon atoms in the formula (I) include Z111 Examples of the alkynyl group include a divalent group having a structure in which one hydrogen atom has been removed from the alkynyl group having 3 to 12 carbon atoms in the above formula. Z 112 In the above, examples of the arylene group having 6 to 12 carbon atoms include Z 111 Examples of the aryl group include a divalent group having a structure in which one hydrogen atom has been removed from the aryl group having 6 to 12 carbon atoms in the above formula. Z 112 The alkenyl group having 2 to 6 carbon atoms, the fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms as the substituent in Z 11 These groups are the same as the alkenyl group having 2 to 6 carbon atoms, the fluorinated alkyl group having 1 to 3 carbon atoms, the chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms as the substituents in the above formula (I). The alkylene group, alkenylene group, and alkynylene group having 3 to 12 carbon atoms, and the arylene group having 6 to 12 carbon atoms may have, as a substituent, one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0131] R 112 When is the alkyl group having 1 to 7 carbon atoms, Z 112 and R 112 are mutually bonded to each other, and these (Z 112 and R 112 ) may form a ring together with the carbon atom to which it is bonded. 112 and R 112 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring.

[0132] In the formula, X 112 is the general formula (101)-2, the general formula (102)-2, or a bromine atom. The bond marked with a symbol * in general formula (101)-2 and the bond marked with a symbol * in general formula (102)-2 are both X 112 The carbon atom to which R is attached (more specifically, 112 , R 122 and Z 112 is formed relative to the carbon atom to which it is bonded.

[0133] In the formula, R 132 is an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms, and these are R 13 in the above, which is the same as the alkyl group having 1 to 12 carbon atoms, the alkoxy group having 1 to 12 carbon atoms, the aryl group having 6 to 10 carbon atoms, the aryloxy group having 6 to 10 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, the aralkyloxy group having 7 to 13 carbon atoms, or the dialkylamino group having 2 to 4 carbon atoms.

[0134] In the formula, R 142 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms, and these are R 14 In the above, it is the same as the alkyl group having 1 to 12 carbon atoms or the aryl group having 6 to 10 carbon atoms.

[0135] Further examples of preferred compounds (10) include compounds represented by the general formula (10) 11 X 11 , R 11 and R 12 is an ethenylene group (***-HC=CH-**) or a group of the general formula "***-R 8 In the formula, the bond marked with the symbol ** is a compound represented by Z 11 The carbon atom to which X is bonded (i.e., X 11 , R 11 and R 12 The bond marked with *** is formed to the carbon atom to which Z is bonded. 11is formed for the carbon atom of the remaining site in the formula 8 is Z 11 The compound (1) or compound (1') obtained by forming a new carbon-silicon (C-Si) bond using such a compound (10) has the general formula "***-HC=CH-CR 11 R 12 -SiR 91 3" or a group represented by the general formula "***-R 8 C=CH-CR 11 R 12 -SiR 91 3". In general, allylsilane-type organosilicon compounds are useful as synthetic intermediates for various compounds, and the allylsilane-type organosilicon compounds, Compound (1) and Compound (1'), are highly useful in industry.

[0136] The compound (10) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0137] <Compound (9)> The compound (9) is represented by the general formula (9). In the formula, R 91 is a group bonded to a silicon atom, and is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group.

[0138] R 91 The alkyl group, aryl group, aralkyl group, alkoxy group, aryloxy group and aralkyloxy group in 13 Examples of the alkyl group, aryl group, aralkyl group, alkoxy group, aryloxy group and aralkyloxy group in the above formula (I) include the same as the alkyl group, aryl group, aralkyl group, alkoxy group, aryloxy group and aralkyloxy group in the above formula (I).

[0139] R 91 Examples of the trialkylsilyloxy group in11 and R 12 and a monovalent group having a structure in which three of the alkyl groups in the above formula are bonded to a silicon atom. R 91 In the trialkylsilyloxy group in the formula (I), the three alkyl groups may be the same or different from one another. That is, the three alkyl groups may all be the same (an example of such a trialkylsilyloxy group is a trimethylsilyloxy group), all be different (an example of such a trialkylsilyloxy group is an ethylmethylpropylsilyloxy group), or only some of them may be the same (an example of such a trialkylsilyloxy group is an ethyldimethylsilyloxy group). R 91 The trialkylsilyloxy group in the formula (I) may have any one of 3 to 36 carbon atoms, 3 to 24 carbon atoms, 3 to 12 carbon atoms, and 3 to 6 carbon atoms.

[0140] In the formula, six R 91 may be the same or different from each other. That is, six R 91 may be all the same, all different, or only some of them may be the same. In terms of ease of obtaining or producing compound (9), it is preferable that the six R 91 are preferably all the same. In compound (9), three R bonded to the silicon atom 91 The combination of the three R may be the same or different between the two silicon atoms. In terms of ease of availability and production of compound (9), 91 are preferably identical to each other between two silicon atoms.

[0141] R 91is preferably an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, an aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms. That is, preferred compounds (9) are those represented by the following general formula (9)-1

[0142] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (sometimes referred to as "compound (9)-1" in this specification).

[0143] More preferred examples of the compound (9) include hexaalkyldisilanes such as hexamethyldisilane; 1,2-dialkoxy-1,1,2,2-tetraalkyldisilanes such as 1,2-di-tert-butoxy-1,1,2,2-tetramethyldisilane; 1,1,2,2-tetraalkyl-1,2-diaralkyldisilanes such as 1,2-dibenzyl-1,1,2,2-tetramethyldisilane; 1,1,2,2-tetraalkyl-1,2-diaryldisilanes such as 1,1,2,2-tetramethyl-1,2-diphenyldisilane and 1,1,2,2-tetramethyl-1,2-bis(4-methylphenyl)disilane; 1,2-dialkyl-1,1,2,2-tetraaryldisilanes such as 1,2-dimethyl-1,1,2,2-tetraphenyldisilane; Examples include 1,2-bis(trialkylsilyloxy)-1,1,2,2-tetraalkyldisilanes such as 1,2-bis(trimethylsiloxy)-1,1,2,2-tetramethyldisilane.

[0144] The compound (9) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0145] <Compound (1)> Compound (1) is one of the target compounds in production method (1) and is represented by the general formula (1). 10 Regardless of the value of n in compound (10), 10 All X's 11 is represented by the general formula "-SiR 91 It has a structure substituted with a group represented by "3".

[0146] In the formula, n 10 , R 11 , R 12 and Z 11 is n in general formula (10) 10 , R 11 , R 12 and Z 11 is the same as R 91 is R in general formula (9) 91 is the same as: n 10 If is 2 or more, n 10 The general formula -SiR 91 The groups represented by "n 3" may be the same or different. 10 The general formula -SiR 91 The groups represented by "3" may all be the same, all be different, or only some may be the same.

[0147] In the reaction step, by adjusting the reaction conditions, it is possible to obtain only one type of compound (1), or two or more types of compound (1), and when two or more types are obtained, the combination and ratio thereof may be adjusted.

[0148] In the production method (1), compound (10)-1 is used as compound (10) and compound (9)-1 is used as compound (9), whereby n 10When is 1, the compound (1) is, for example, a compound represented by the following general formula (1)-1

[0149] [ka] (In the formula, R 111 , R 121 , Z 111 and R 911 is the same as above.) (sometimes referred to as "compound (1)-1" in this specification) can be suitably obtained.

[0150] In the production method (1), compound (10)-2 is used as compound (10) and compound (9)-1 is used as compound (9), whereby n 10 When is 2, the compound (1) may be, for example, a compound represented by the following general formula (1)-2

[0151] [ka] (In the formula, R 112 , R 122 , Z 112 and R 911 is the same as above.) (sometimes referred to as "compound (1)-2" in this specification) can be suitably obtained.

[0152] When compound (10)-1 or compound (10)-2, and compound (9)-1 are used in the reaction step of production method (1), the catalyst may be, for example, zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or a compound in which gold is supported on carbon.

[0153] <Compound (1')> Compound (1') is another type of target compound in production method (1) and is represented by the general formula (1'). Compound (1') is a compound represented by the general formula (1') 10 is an integer of 2 or more, and 10Of these, n 12 X's 11 is unreacted and n 11 X's 11 is represented by the general formula "-SiR 91 It has a structure substituted with a group represented by "3".

[0154] In the formula, n 11 is the general formula "-CR 11 R 12 SiR 91 Z of the group represented by "3" 11 is the number of bonds to the n 11 is Z 11 Although it is determined depending on the type of, it is preferably 1 to 3, and more preferably 1 or 2. Such a compound (1') can be produced more easily. In the formula, n 12 is the general formula "-CR 11 R 12 X 11 Z of the group represented by 11 is the number of bonds to the n 12 is Z 11 Although it is determined depending on the type of, it is preferably 1 to 3, and more preferably 1 or 2. Such a compound (1') can be produced more easily. However, n 11 +n 12 =n 10 and n 11 +n 12 The compound (1) is represented by the general formula (1'), where n 12 When the definition of is changed to "an integer greater than or equal to 0", 12 corresponds to the compound where is 0.

[0155] In the formula, n 10 , R 11 , R 12 , Z 11 and X 11 is n in general formula (10) 10 , R 11 , R 12 , Z 11and X 11 is the same as R 91 is R in general formula (9) 91 is the same as:

[0156] n 11 If is 2 or more, n 11 R 11 may be the same or different from each other. That is, n 11 R 11 may all be the same, may all be different, or may only be partially the same. n 11 If is 2 or more, n 11 R 12 may be the same or different from each other. That is, n 11 R 12 may all be the same, may all be different, or may only be partially the same. n 11 If is 2 or more, n 11 The general formula -SiR 91 The groups represented by "n 3" may be the same or different. 11 The general formula -SiR 91 The groups represented by "3" may all be the same, all be different, or only some may be the same.

[0157] n 12 If is 2 or more, n 12 R 11 may be the same or different from each other. That is, n 12 R 11 may all be the same, may all be different, or may only be partially the same. n 12 If is 2 or more, n 12 R 12 may be the same or different from each other. That is, n 12 R 12 may all be the same, may all be different, or may only be partially the same. n 12 If is 2 or more, n 12 X's 11 may be the same or different from each other. That is, n 12 X's 11 may all be the same, may all be different, or may only be partially the same.

[0158] In the compound (1) or compound (1'), Z 11 When the hydrocarbon group in the formula (I) is a group having an unsaturated hydrocarbon ring, the unsaturated hydrocarbon ring may form a coordinate bond with a metal to chelate it.

[0159] Preferred examples of the compound (1) or compound (1′) include compounds represented by the general formula (1) or (1′) below, where Z 11 The general formula of -SiR 91 3”, R 11 and R 12 is an ethenylene group (***-HC=CH-**) or a group of the general formula "***-R 8 In the formula, the bond marked with the symbol ** is a compound represented by Z 11 The carbon atom to which the bond is made (i.e., the general formula "-SiR 91 3”, R 11 and R 12 The bond marked with *** is formed to the carbon atom to which Z is bonded. 11 is formed for the carbon atom of the remaining site in the formula 8 is the above-mentioned substituent. As described above, such a compound (1) or compound (1′) can be prepared by reacting a compound represented by the general formula “***-HC═CH—CR 11 R 12 -SiR 91 3" or a group represented by the general formula "***-R 8 C=CH-CR 11 R 12 -SiR 91It is an allylsilane-type organosilicon compound having a group represented by "3", and is highly useful in industry.

[0160] In the reaction step, by adjusting the reaction conditions, it is possible to obtain only one type of compound (1'), or two or more types, and when two or more types are obtained, the combination and ratio thereof may be adjusted.

[0161] <Other ingredients> In the reaction step, a component other than compound (10), compound (9), or the catalyst may be used (the reaction may be carried out by adding another component) within a range that does not impair the effects of the present invention.

[0162] The other component used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0163] The other components can be selected arbitrarily depending on the purpose and are not particularly limited.

[0164] [solvent] A preferred example of the other component is a solvent. By using a solvent to dissolve either or both of compound (10) and compound (9) and then carrying out the reaction, the yield of compound (1) or compound (1') can be increased. In this specification, unless otherwise specified, the term "solvent" refers not only to a component capable of dissolving a solute in a solution, but also to a component that serves as a dispersion medium in a dispersion liquid.

[0165] The solvent is not particularly limited as long as it is liquid at room temperature, but it is preferable that the solvent is not reactive with both compound (10) and compound (9).

[0166] In this specification, "room temperature" means a temperature that is neither particularly cold nor hot, that is, an ordinary temperature, and examples thereof include temperatures of 15 to 25°C.

[0167] Preferred examples of the solvent include aromatic hydrocarbons such as toluene, benzene, o-xylene (1,2-dimethylbenzene), m-xylene (1,3-dimethylbenzene), and p-xylene (1,4-dimethylbenzene); cyclic ethers such as 1,4-dioxane and tetrahydrofuran (THF); and halogenated aromatic hydrocarbons such as benzotrifluoride.

[0168] The solvent used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0169] <Reaction conditions> In the reaction step, to obtain compound (1), the amount of compound (9) used is preferably 1-fold molar amount or more, and may be, for example, 2-fold molar amount or more, of the amount of compound (10) used. When the amount of compound (9) used is the lower limit or more, the yield of compound (1) becomes higher. The upper limit of the amount of compound (9) used is not particularly limited. In order to prevent excessive use of compound (9), the amount of compound (9) used is preferably 10 times the molar amount of compound (10) or less.

[0170] In the reaction step, in order to obtain compound (1'), the amount of compound (9) used is n 11 or n 12 Although it also depends on the amount of compound (9), it is preferably 0.5 to 2 times the molar amount of compound (10) used, and may be, for example, 1 to 2 times the molar amount. When the amount of compound (9) used is in such a range, the yield of compound (1') becomes higher.

[0171] In the reaction step, the amount of the catalyst used is preferably an amount such that the amount of gold in the catalyst is 0.005 times or more, or may be 0.01 times or more, or 0.02 times or more, by molar ratio relative to the amount of compound (10) used. When the amount of the catalyst used is equal to or greater than the lower limit, the yield of compound (1) or compound (1') is increased. The upper limit of the amount of the catalyst used is not particularly limited. In order to prevent excessive use of the catalyst, the amount of the catalyst used is preferably an amount such that the amount of gold in the catalyst is 0.1 times or less the molar amount of compound (10) used.

[0172] When a solvent is used in the reaction step, the amount of the solvent used is preferably 0.5 L or more per 1 mol of compound (10), and may be, for example, 0.8 L or more. When the amount of the solvent used is equal to or more than the lower limit, the effect obtained by using the solvent is further enhanced. The upper limit of the amount of the solvent used is not particularly limited. In order to prevent excessive use of the solvent, the amount of the solvent used is preferably 5 L or less per 1 mol of compound (10).

[0173] In the reaction step, the reaction temperature may be, for example, 55° C. or higher, preferably 75° C. or higher, and also preferably 90° C. or higher. When the reaction temperature is equal to or higher than the lower limit, the yield of compound (1) or compound (1′) becomes higher. The upper limit of the reaction temperature is not particularly limited, but the reaction temperature is preferably 140° C. or lower, since this avoids excessive heating of the reaction solution and increases the effect of suppressing the generation of impurities.

[0174] In the reaction step, the reaction time can be appropriately adjusted taking into consideration other reaction conditions such as the reaction temperature. Usually, the reaction time is preferably 0.5 hours or more, and may be, for example, 1 hour or more, 5 hours or more, or 10 hours or more. When the reaction time is equal to or more than the lower limit, the yield of compound (1) or compound (1') becomes higher. The upper limit of the reaction time is not particularly limited, but in order to avoid the problem that the yield of the target product does not increase even when the reaction time is extended, it is usually preferable that the reaction time be 30 hours or less. The reaction times shown here are particularly suitable when the reaction temperature is within the above range, for example.

[0175] In the reaction step, the reaction of compound (10) with compound (9) in the presence of the catalyst may be carried out in an atmosphere of an inert gas such as argon gas, helium gas, or nitrogen gas, or in an air atmosphere. However, in terms of increasing the yield of compound (1) or compound (1'), it is preferable to carry out the reaction of compound (10) with compound (9) in the presence of the catalyst under dehydration conditions. To this end, it is preferable to use compound (10), compound (9), the catalyst, and, if necessary, the solvent, which have been dehydrated by a known method.

[0176] In production method (1), after completion of the reaction step, compound (1) or compound (1') can be isolated by performing post-treatment using a known method, if necessary. That is, as needed, post-treatment procedures such as filtration, washing, extraction, pH adjustment, dehydration, and concentration can be performed, either alone or in combination, and compound (1) or compound (1') can be isolated by concentration, crystallization, reprecipitation, column chromatography, etc. Furthermore, the isolated compound (1) or compound (1') can be further purified, if necessary, by performing crystallization, reprecipitation, column chromatography, extraction, stirring and washing of crystals with a solvent, either alone or in combination, once or more times. Alternatively, after completion of the reaction step, compound (1) or compound (1') can be used for the intended purpose without isolation, after performing post-treatment as needed. For example, compound (1) or compound (1') can be subjected to the next intended reaction without isolation.

[0177] The structures of Compound (1) and Compound (1') can be confirmed by known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), and infrared spectroscopy (IR).

[0178] In production method (1), after the reaction step, the catalyst used in the reaction step may be recovered, and the recovered catalyst may be used to carry out the reaction step again, a re-reaction step being carried out one or more times. The catalyst is solid, and after the reaction, contamination of compound (1) or compound (1') can be avoided. It can be easily recovered by filtering and washing, and can be reused repeatedly. Furthermore, even when the catalyst is reused in this way, compound (1) or compound (1') can be obtained at the same reaction rate and yield as when a non-recycled catalyst is used, and therefore production method (1) has excellent suitability for catalyst reuse.

[0179] When the catalyst is to be reused, it is preferable to wash the catalyst taken out from the reaction solution with a solvent and dry it before reuse. In this case, examples of the washing solvent include ethers such as diethyl ether. The catalyst after washing may be dried by any of atmospheric drying, reduced pressure drying, and air drying, or by heated drying (for example, heated atmospheric drying, heated reduced pressure drying, and heated air drying).

[0180] The re-reaction step may be the same as the reaction step, except that the recovered catalyst is used as the catalyst.

[0181] A preferred example of the production method (1) is a production method (sometimes referred to as "production method (1)-1" in this specification) in which compound (10) is compound (10)-1, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (1) is compound (1)-1. That is, the production method (1)-1 is a method in which compound (10) is compound (10)-1

[0182] [ka] (In the formula, R 111 and R 121are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 111 and R 121 at least one of is a hydrogen atom; Z 111 represents an alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 111 When is the alkyl group having 1 to 7 carbon atoms, Z 111 and R 111 may be bonded to each other to form a ring; X 111 is represented by the following general formula (101)-1

[0183] [ka] (In the formula, R 131 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X 111 is formed with respect to the carbon atom to which the following is bonded.)

[0184] [ka] (In the formula, R 141 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 111a compound (10)-1) represented by the formula (I) or a bromine atom, The following general formula (9)-1

[0185] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (1-1)

[0186] [ka] (In the formula, R 111 , R 121 , Z 111 and R 911 is the same as above.) The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0187] Another preferred example of the production method (1) is a production method (sometimes referred to as "production method (1)-2" in this specification) in which compound (10) is compound (10)-2, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (1) is compound (1)-2. That is, the production method (1)-1 may be a production method in which compound (10)-2 is represented by the following general formula (10)-2.

[0188] [ka] (In the formula, R 112 and R122 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 112 and R 122 At least one of R is a hydrogen atom, and two R 112 may be the same or different, and two R 122 may be the same or different from each other; Z 112 represents an alkylene group, alkenylene group, or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 112 When is the alkyl group having 1 to 7 carbon atoms, Z 112 and R 112 may be bonded to each other to form a ring; X 112 is represented by the following general formula (101)-2

[0189] [ka] (In the formula, R 132 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; a bond marked with an * represents X 112 is formed with respect to the carbon atom to which the following is bonded.)

[0190] [ka] (In the formula, R 142 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 112a compound (10)-2) represented by the formula (I) or a bromine atom, The following general formula (9)-1

[0191] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (1)-2

[0192] [ka] (In the formula, R 112 , R 122 , Z 112 and R 911 is the same as above.) (compound (1)-2), The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0193] When compound (10)-1 is used, that is, n 10 is 1, and compound (1)-2 is compound (10)-2, that is, n 10 is compound (1) when n is 2. 10 An example of a method for producing compound (1) using a preferred compound (10) in which R is not limited to 1 or 2 is a method for producing compound (1) using a compound represented by the following general formula (10)-01

[0194] [ka] (In the formula, n 010is an integer greater than or equal to 1; R 011 and R 012 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 011 and R 012 At least one of is a hydrogen atom, and n 010 If is 2 or more, n 010 R 011 may be the same or different, and n 010 R 012 may be the same or different from each other; Z 011 represents a hydrocarbon group having 3 to 14 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 011 When Z is the hydrocarbon group having 3 to 14 carbon atoms which may have a substituent, 011 and R 011 may be bonded to each other to form a ring; X 011 is represented by the following general formula (101)-01

[0195] [ka] (In the formula, R 013 represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X 011 is formed with respect to the carbon atom to which the following is bonded.)

[0196] [ka] (In the formula, R 014 represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X 011 is formed with respect to the carbon atom to which n is bonded. 010 If is 2 or more, n 010 X's 011 may be the same or different from each other.) (in this specification, may be referred to as "compound (10)-01"), The following general formula (9)-1

[0197] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), In the presence of a catalyst, the following general formula (1-01)

[0198] [ka] (In the formula, n 010 , R 011 , R 012 , Z 011 and R 911 is the same as above, and the general formula "-SiR 911 Three R's in "3" 911 may be the same or different, and n 010 If is 2 or more, n 010 R 011 may be the same or different, and n 010 R 012 may be the same or different, and n 010 The general formula -SiR 911The groups represented by "3" may be the same or different from each other.) (in this specification, this may be referred to as "compound (1)-01"); 010 is an integer of 2 or more, the following general formula (1')-01

[0199] [ka] (In the formula, n 011 and n 012 are each independently an integer of 1 or more, provided that n 011 +n 012 =n 010 (≥2); n 010 , R 011 , R 012 , Z 011 , X 011 and R 911 is the same as above; General formula “-SiR 911 Three R's in "3" 911 may be the same or different: n 011 If is 2 or more, n 011 R 011 may be the same or different, and n 011 R 012 may be the same or different, and n 011 The general formula -SiR 911 The groups represented by "3" may be the same or different from each other; n 012 If is 2 or more, n 012 R 011 may be the same or different, and n 012 R 012 may be the same or different, and n 012 X's 011 may be the same or different from each other.) (in this specification, it may be referred to as "compound (1')-01"), The method for producing a compound includes a method in which the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0200] In the formula, n 010 is an integer equal to or greater than 1, and 10 is the same as: In the formula, R 011 and R 012 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. 011 and R 012 In the formula, the alkyl groups having 1 to 7 carbon atoms are R 112 and R 122 At least one of the R 111 The same applies to the alkyl group having 1 to 7 carbon atoms in the above.

[0201] In the formula, Z 011 may have a substituent, n 010 Valence, or n 011 +n 012 It is a hydrocarbon group having 3 to 14 carbon atoms. Z 011 Among the hydrocarbon groups having 3 to 14 carbon atoms which may have a substituent, examples of the monovalent group include Z 111 Examples of the alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, are the same as those in Z 011 Among the hydrocarbon groups having 3 to 14 carbon atoms which may have a substituent, examples of the divalent group include Z 112 Examples thereof include alkylene groups, alkenylene groups or alkynylene groups having 3 to 12 carbon atoms which may have a substituent, and arylene groups having 6 to 12 carbon atoms which may have a substituent, as in the above.

[0202] R 011When Z is the hydrocarbon group having 3 to 14 carbon atoms which may have a substituent, 011 and R 011 are mutually bonded to each other, and these (Z 011 and R 011 ) may form a ring together with the carbon atom to which it is bonded. 011 and R 011 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring.

[0203] In the formula, R 013 is an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms, and these are R 13 in the above, which is the same as the alkyl group having 1 to 12 carbon atoms, the alkoxy group having 1 to 12 carbon atoms, the aryl group having 6 to 10 carbon atoms, the aryloxy group having 6 to 10 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, the aralkyloxy group having 7 to 13 carbon atoms, or the dialkylamino group having 2 to 4 carbon atoms. In the formula, R 014 is an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms, and these are R 14 In the above, it is the same as the alkyl group having 1 to 12 carbon atoms or the aryl group having 6 to 10 carbon atoms. The bond marked with a symbol * in the general formula (101)-01 and the bond marked with a symbol * in the general formula (102)-01 are both X 011 The carbon atom to which R is attached (more specifically, 011 , R 012 and Z 011 is formed relative to the carbon atom to which it is bonded.

[0204] In the formula, n 011 and n 012 are each independently an integer of 1 or more, and are the same as the n 11 and n 12 Same as n011 +n 012 =n 010 (≧2).

[0205] In the reaction step of the production method (1), X in the compound (10) 11 and X 11 The carbon atom to which R 11 , R 12 and Z 11 It is presumed that the bond between the carbon atom to which the carbon atom is bonded and the carbon-oxygen (CO) bond or the carbon-bromine (C-Br) bond is broken by the action of the catalyst, generating a carbon radical (C·), which triggers the formation of a new carbon-silicon (C-Si) bond, thereby producing compound (1) or compound (1'). In that the carbon radical (C·) is generated by the action of the catalyst, which triggers the subsequent reaction to form a new carbon-silicon bond, production method (1) has something in common with production methods (2) to (5) described below.

[0206] According to production method (1), by using the catalyst, compound (1) or compound (1') can be easily produced using compound (10) and compound (9) as raw materials. During this reaction, a carbon-oxygen (CO) bond or a carbon-bromine (C-Br) bond in compound (10) is cleaved, and a new carbon-silicon (C-Si) bond is formed, which is a novel reaction not previously known. Furthermore, the catalyst can be easily recovered and repeatedly reused. Thus, the reaction of compound (10) and compound (9) in the presence of the catalyst to obtain compound (1) or compound (1') is extremely useful as a synthetic reaction for organosilicon compounds.

[0207] Additionally, X 11 is a group represented by general formula (101), the compound (10) is a carboxylic acid ester, a urethane or a carbonate ester, and X 11 is a group represented by general formula (102), the compound (10) is an ether, and X 11When is a bromine atom, compound (10) is a bromide, which is relatively stable and can be produced simply and easily from an alcohol. Furthermore, these raw materials are readily available as a wide variety of commercial products. Furthermore, these raw materials are relatively inexpensive. Compound (9) is also easy to produce or obtain, is relatively stable, and is relatively inexpensive. Furthermore, because compound (10) and compound (9) are relatively stable, compound (1) or compound (1'), which could not be produced by conventional methods, can be easily produced. Thus, production method (1) exhibits significant advantages in terms of usefulness and versatility.

[0208] <<Manufacturing method (2)>> A method for producing a compound according to one embodiment of the present invention (sometimes referred to herein as "production method (2)") comprises reacting a compound represented by the following general formula (20):

[0209] [ka] (In the formula, Z 21 is a hydrocarbon group which may have a substituent, and a carbon atom in the hydrocarbon group may be substituted with a nitrogen atom together with a hydrogen atom bonded to the carbon atom (sometimes referred to as "compound (20)" in this specification), The following general formula (9)

[0210] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) (i.e., compound (9)), in the presence of a catalyst to form a compound represented by the following general formula (2):

[0211] [ka] (In the formula, Z 21 and R 91 is the same as above.) (sometimes referred to as "compound (2)" in this specification), The catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0212] According to the production method (2), by using the catalyst, the versatile compound (20) and compound (9) are used as raw materials to form a carbon-silicon bond, thereby obtaining compound (2) as an organosilicon compound.

[0213] <Catalyst> The catalyst and its production method in the production method (2) are the same as the catalyst and its production method in the production method (1).

[0214] The catalyst used in the reaction step of the production method (2) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0215] The catalyst in production method (2) is preferably a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetroxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon. Use of such a catalyst allows compound (2) to be obtained more easily and in a higher yield.

[0216] <Compound (20)> The compound (20) is represented by the general formula (20). In the formula, Z 21 is a divalent hydrocarbon group which may have a substituent. Z 21The hydrocarbon group in may be linear, branched, or cyclic, and may have both a linear structure (linear or branched) and a cyclic structure. When the hydrocarbon group has a cyclic structure, including when it is cyclic, the cyclic structure may be either an aliphatic hydrocarbon ring (e.g., an aliphatic hydrocarbon group) or an aromatic hydrocarbon ring (e.g., an aromatic hydrocarbon group), and may be either monocyclic or polycyclic. The hydrocarbon group may be either a saturated hydrocarbon group or an unsaturated hydrocarbon group, and may be either an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

[0217] Z 21 The hydrocarbon group in the formula (I) preferably has 1 to 10 carbon atoms, more preferably 1 to 6 carbon atoms, and may have, for example, 1 to 5 carbon atoms, 2 to 6 carbon atoms, or 2 to 5 carbon atoms.

[0218] Z 21 Preferred examples of the hydrocarbon group in the formula (I) include an alkylene group, an alkenylene group, an alkadienylene group, an alkynylene group, and an arylene group.

[0219] Z 21 The alkylene group, alkenylene group, alkynylene group, and arylene group in 11 Examples of the alkylene group, alkenylene group, alkynylene group and arylene group in the above formula (I) include the same as the alkylene group, alkenylene group, alkynylene group and arylene group in the above formula (I). Z 21 Examples of the alkadienylene group in the above formula include groups having a structure in which one single bond (CC) between carbon atoms in the alkenylene group is replaced with a double bond (C=C). In the alkadienylene group, it is preferred that the two double bonds between carbon atoms are not adjacent to each other (in other words, one carbon atom is not involved in the formation of two double bonds). Among these, Z 21 The hydrocarbon group in the formula (I) is more preferably an alkylene group having 1 to 5 carbon atoms or an alkenylene group having 2 to 6 carbon atoms.

[0220] Z 21The hydrocarbon group in the formula (I) may or may not have a substituent. Z 21 When the hydrocarbon group in formula (I) has two or more substituents, these substituents may be the same or different from one another, i.e., all the substituents may be the same, all the substituents may be different, or only some of the substituents may be the same. Z 21 The bonding position of the substituent in the hydrocarbon group in the formula (I) is not particularly limited, and the substituent may be bonded to a terminal carbon atom of the hydrocarbon group or to a non-terminal carbon atom. Z 21 When the hydrocarbon group has two or more substituents, the multiple (2 to 3) substituents may be bonded to the same carbon atom, or the substituents may be bonded to different carbon atoms.

[0221] Z 21 Examples of the substituent carried by the hydrocarbon group in the formula (I) include a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 6 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0222] Z 21 In the above substituents, examples of the alkenyl group having 2 to 6 carbon atoms, the fluorinated alkyl group having 1 to 3 carbon atoms, the chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms include Z 11 Examples of the substituents include the same alkenyl group having 2 to 6 carbon atoms, the fluorinated alkyl group having 1 to 3 carbon atoms, the chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms. Z 21 The aryl group having 6 to 10 carbon atoms in the substituents in R 14 Examples of the aryl group include the same aryl groups having 6 to 10 carbon atoms as those mentioned above.

[0223] Z21 In the formula, the carbon atoms in the hydrocarbon group may be substituted with nitrogen atoms, together with the hydrogen atoms bonded to the carbon atoms. For example, the group represented by the formula "-CH(-)-" in the hydrocarbon group may be substituted with a group represented by the formula "-N(-)-", and the group represented by the formula "-CH=" may be substituted with a group represented by the formula "-N=". The number of carbon atoms substituted in this way is Z 21 Although it is determined depending on the type of, it is preferably 1 or 2, and more preferably 1. Such a compound (20) is easier to produce or obtain.

[0224] An example of a preferred compound (20) is a compound represented by the following general formula (20)-1

[0225] [ka] (wherein m1 is an integer of 1 to 5; R 211 and R 212 are each independently a hydrogen atom, an alkyl group of 1 to 7 carbon atoms which may have a substituent, an alkenyl group of 2 to 7 carbon atoms which may have a substituent, or an aryl group of 6 to 10 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group of 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group of 1 to 3 carbon atoms, an acyloxy group of 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group, and when m1 is 2 or more, 211 may be the same or different, and m R 212 may be the same or different, and R 211 and R 212 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 211 and R 212may be bonded to each other to form a ring, m1 is 2 or more, and R 211 Comrades or R 212 When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R 211 R 212 may be bonded to each other to form a ring, and R 211 and R 212 When either or both of R 211 and R 212 may be replaced with a nitrogen atom, together with the hydrogen atom attached to said carbon atom; m2 is 0 or 1; R 213 and R 214 each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 213 and R 214 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 213 and R 214 may be bonded to each other to form a ring) (sometimes referred to as “compound (20)-1” in this specification).

[0226] In the formula, m1 is a group represented by the general formula "-CR 211 R 212 -” and is an integer of 1 to 5. m1 is preferably 1 to 3, more preferably 1 to 8, and more preferably 1 to 6, and may be, for example, 1 to 4. Such a compound (20) is easier to produce or obtain.

[0227] In the formula, R 211 and R 212 are each independently a hydrogen atom, an optionally substituted alkyl group having 1 to 7 carbon atoms, an optionally substituted alkenyl group having 2 to 7 carbon atoms, or an optionally substituted aryl group having 6 to 10 carbon atoms. R 211 and R 212 In the above, the alkyl group having 1 to 7 carbon atoms and the alkenyl group having 2 to 7 carbon atoms include R 11 and R 12 Examples of the alkyl group having 1 to 7 carbon atoms and the alkenyl group having 2 to 7 carbon atoms in R 211 and R 212 In the formula (I), the aryl group having 6 to 10 carbon atoms includes R 13 Examples of the aryl group include the same as the aryl group having 6 to 10 carbon atoms.

[0228] R 211 and R 212 As the alkenyl group having 2 to 6 carbon atoms, the fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms as the substituent in 11 Examples of the substituent in the formula (I) include the same as the alkenyl group having 2 to 6 carbon atoms, the fluorinated alkyl group having 1 to 3 carbon atoms, the chlorinated alkyl group having 1 to 3 carbon atoms, and the acyloxy group having 2 to 4 carbon atoms. R 211 and R 212In the above formula (I), the alkyl group having 1 to 7 carbon atoms, the alkenyl group having 2 to 7 carbon atoms, and the aryl group having 6 to 10 carbon atoms may have, as a substituent, one or more substituents selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group.

[0229] If m1 is 2 or more, m1 R 211 may be the same or different from each other. That is, m R 211 may all be the same, may all be different, or may only be partially the same. If m1 is 2 or more, m1 R 212 may be the same or different from each other. That is, m R 212 may all be the same, may all be different, or may only be partially the same.

[0230] R attached to the same carbon atom 211 and R 212 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 211 and R 212 are mutually bonded to each other, and these (R 211 and R 212 ) may form a ring together with the carbon atom to which it is bonded. 211 and R 212 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring. For example, R 211 and R 212 are all the above alkenyl groups, these alkenyl groups may be bonded to each other to form an aromatic hydrocarbon ring together with the carbon atoms to which these alkenyl groups are bonded.

[0231] m1 is 2 or more, that is, compound (20) is represented by the general formula "-CR 211 R 212 -" and R bonded to adjacent carbon atoms in this repeating structure. 211 Comrades or R 212 When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R 211 R 212 are mutually bonded to each other, and these (R 211 Comrades or R 212 (each other) may form a ring together with the carbon atom to which they are bonded. 211 Comrades or R 212 The embodiment in which they are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring. For example, R 211 Comrades or R 212 When both are the above-mentioned alkenyl groups, these alkenyl groups may be bonded to each other to form an aromatic hydrocarbon ring together with the carbon atoms to which these alkenyl groups are bonded.

[0232] R 211 and R 212 When either or both of R 211 and R 212 The carbon atom to which is bonded may be substituted with a nitrogen atom together with the hydrogen atom bonded to the carbon atom. For example, a group represented by the formula "-CH(-)-" may be substituted with a group represented by the formula "-N(-)-", and a group represented by the formula "-CH=" may be substituted with a group represented by the formula "-N=". The number of carbon atoms substituted in this manner is determined depending on the type of m1, but is preferably 1 or 2, and more preferably 1. Such a compound (20)-1 is easier to produce or obtain.

[0233] In the formula, m2 is the general formula “-CR 213 =CR 214 m2 is the number of repeats of the group represented by the general formula "-CR 211 R 212 R in the group represented by "-" 211 and R 212 Of the carbon atoms to which is bonded, the carbon atom closest to the oxygen atom in general formula (20)-1 is directly bonded to the oxygen atom.

[0234] In the formula, R 213 and R 214 are each independently a hydrogen atom, an alkyl group of 1 to 7 carbon atoms which may have a substituent, an alkenyl group of 2 to 7 carbon atoms which may have a substituent, or an aryl group of 6 to 10 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group of 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group of 1 to 3 carbon atoms, an acyloxy group of 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group. R 213 and R 214 The alkyl group having 1 to 7 carbon atoms which may have a substituent, the alkenyl group having 2 to 7 carbon atoms which may have a substituent, and the aryl group having 6 to 10 carbon atoms which may have a substituent in the formula (I) include R 211 and R 212 Examples of the alkyl group include the alkyl group having 1 to 7 carbon atoms which may have a substituent, the alkenyl group having 2 to 7 carbon atoms which may have a substituent, and the aryl group having 6 to 10 carbon atoms which may have a substituent.

[0235] R 213 and R 214 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 213 and R 214 are mutually bonded to each other, and these (R 213 and R 214) may form a ring together with the carbon atom to which it is attached. At this time, R 213 and R 214 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring (or R 211 and R 212 are bonded to each other to form a ring). For example, R 213 and R 214 may be bonded to each other to form an aromatic hydrocarbon ring together with the carbon atoms to which they are attached.

[0236] The compound (20) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0237] <Compound (9)> The compound (9) in the production method (2) is the same as the compound (9) in the production method (1).

[0238] A preferred compound (9) in the production method (2) is a compound represented by the following general formula (9)-1

[0239] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) that is, compound (9)-1.

[0240] More preferred compounds (9) in the production method (2) include the same as the more preferred compounds (9) in the production method (1).

[0241] The compound (9) used in the reaction step of the production method (2) may be one type or two or more types. When two or more types are used, the combination and ratio thereof can be arbitrarily selected depending on the purpose.

[0242] <Compound (2)> Compound (2) is the target product of production method (2) and is represented by the above general formula (2). In the formula, Z 21 is Z in general formula (20) 21 is the same as R 91 is R in general formula (9) 91 is the same as:

[0243] In the production method (2), compound (20)-1 is used as compound (20) and compound (9)-1 is used as compound (9), and thus compound (2) can be prepared, for example, by using a compound represented by the following general formula (2)-1

[0244] [ka] (In the formula, m1, m2, R 211 , R 212 , R 213 , R 214 and R 911 is the same as above.) (sometimes referred to as "compound (2)-1" in this specification) can be suitably obtained.

[0245] When compound (20)-1 and compound (9)-1 are used in the reaction step of production method (2), the catalyst may be, for example, zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or a compound in which gold is supported on carbon.

[0246] <Other ingredients> In the reaction step of production method (2), a component other than compound (20), compound (9), or the catalyst may be used (the reaction may be carried out by adding another component) within a range that does not impair the effects of the present invention.

[0247] The other component used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0248] The other components can be selected arbitrarily depending on the purpose and are not particularly limited.

[0249] [solvent] A preferred example of the other component is the same solvent as in the production method (1). By dissolving either or both of compound (20) and compound (9) in a solvent and carrying out the reaction, the yield of compound (2) can be increased. The solvent is preferably one that is unreactive with both compound (20) and compound (9).

[0250] As in the case of Production Method (1), preferred examples of the solvent in Production Method (2) include aromatic hydrocarbons such as toluene, benzene, o-xylene (1,2-dimethylbenzene), m-xylene (1,3-dimethylbenzene), and p-xylene (1,4-dimethylbenzene); cyclic ethers such as 1,4-dioxane and tetrahydrofuran (THF); and halogenated aromatic hydrocarbons such as benzotrifluoride.

[0251] The solvent used in the reaction step of the production method (2) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0252] <Reaction conditions> The reaction conditions in the reaction step of Production Method (2) (e.g., the amount of compound (9) used, the amount of the catalyst used, the amount of solvent used, the reaction temperature, the reaction time, the atmosphere, etc.) can be the same as the reaction conditions in the reaction step of Production Method (1) (particularly, the reaction conditions for producing Compound (1)), except that Compound (20) is used instead of Compound (10).

[0253] In Production Method (2), after completion of the reaction step, compound (2) can be isolated by performing post-treatment, if necessary, using a known method, as in Production Method (1). The isolated compound (2) may be purified as in Production Method (1), or, after completion of the reaction step, compound (2) may be used for the intended purpose without being isolated, after performing post-treatment, if necessary.

[0254] The structure of compound (2) can be confirmed by known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), and infrared spectroscopy (IR).

[0255] In production method (2), as in production method (1), after the reaction step, the catalyst used in the reaction step may be recovered, and the recovered catalyst may be used to carry out the reaction step again, a re-reaction step being carried out one or more times. The catalyst is solid, and after the reaction, contamination of compound (2) can be avoided. It can be easily recovered by filtering and washing, and can be reused repeatedly. Furthermore, even when the catalyst is reused in this way, compound (2) can be obtained at the same reaction rate and yield as when a non-recycled catalyst is used, and therefore production method (2) has excellent suitability for catalyst reuse.

[0256] In the production method (2), the catalyst can be reused (for example, washed and dried) in the same manner as in the production method (1).

[0257] In the production method (2), the re-reaction step may be the same as the reaction step, except that the recovered catalyst is used as the catalyst.

[0258] A preferred example of production method (2) is a production method in which compound (20) is compound (20)-1, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (2) is compound (2)-1 (sometimes referred to as “production method (2)-1” in this specification). That is, in the production method (2)-1, a compound represented by the following general formula (20)-1

[0259] [ka] (wherein m1 is an integer of 1 to 5; R 211 and R 212 are each independently a hydrogen atom, an alkyl group of 1 to 7 carbon atoms which may have a substituent, an alkenyl group of 2 to 7 carbon atoms which may have a substituent, or an aryl group of 6 to 10 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group of 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group of 1 to 3 carbon atoms, an acyloxy group of 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group, and when m1 is 2 or more, 211 may be the same or different, and m R 212 may be the same or different, and R 211 and R 212 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 211 and R 212 may be bonded to each other to form a ring, m1 is 2 or more, and R 211 Comrades or R 212 When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R211 R 212 may be bonded to each other to form a ring, and R 211 and R 212 When either or both of R 211 and R 212 may be replaced with a nitrogen atom, together with the hydrogen atom attached to said carbon atom; m2 is 0 or 1; R 213 and R 214 each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 213 and R 214 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 213 and R 214 may be bonded to each other to form a ring (compound (20)-1), The following general formula (9)-1

[0260] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (2)-1

[0261] [ka] (In the formula, m1, m2, R 211 , R 212 , R 213 , R 214 and R 911 is the same as above.) The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0262] In the reaction step of the production method (2), Z in the compound (20) 21 And Z 21 It is presumed that the bond between the carbon atom to which is bonded and the carbon-oxygen (CO) bond is broken by the action of the catalyst, generating a carbon radical (C·), which triggers the formation of a new carbon-silicon (C-Si) bond, thereby producing compound (2). In that the action of the catalyst generates the carbon radical (C·), which triggers the subsequent reaction to form a new carbon-silicon bond, production method (2) has something in common with production method (1) and production methods (3) to (5) described below.

[0263] According to production method (2), by using the catalyst, compound (2) can be easily produced using compound (20) and compound (9) as raw materials. During this reaction, the carbon-oxygen (CO) bond in compound (20) is broken, and a new carbon-silicon (C-Si) bond is formed, which is a novel reaction not previously known. Furthermore, the catalyst can be easily recovered and reused repeatedly. Thus, the reaction of compound (20) with compound (9) in the presence of the catalyst to obtain compound (2) is extremely useful as a synthetic reaction for organosilicon compounds.

[0264] Furthermore, compound (20) is relatively stable and can be produced simply and easily from an alcohol. Compound (20) is readily available as a variety of commercially available products. Compound (20) is also relatively inexpensive. Compound (9) is also easily produced or readily available, relatively stable, and relatively inexpensive. Furthermore, because compound (20) and compound (9) are relatively stable, compound (2), which could not be produced by conventional methods, can be easily produced. Thus, production method (2) exhibits significant advantages in terms of usefulness and versatility.

[0265] <<Manufacturing method (3)>> A method for producing a compound according to one embodiment of the present invention (sometimes referred to herein as "production method (3)") comprises reacting a compound represented by the following general formula (30):

[0266] [ka] (wherein l1 is an integer of 2 or more; l2 is 0 or 1; R 31 is an alkylene group, one or more methylene groups in the alkylene group may be substituted with an arylene group, and 11 R 31 may be the same or different from each other; R 32 is an alkylene group or an arylene group, and when l2 is 1, l1 R 32 may be the same or different from each other; wherein the terminal carboxy group may form a salt.) (sometimes referred to as "compound (30)" in this specification), The following general formula (9)

[0267] [ka] (In the formula, R 91is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) (i.e., compound (9)), in the presence of a catalyst to form a compound represented by the following general formula (3):

[0268] [ka] (In the formula, R 31 and R 91 is the same as above.) (sometimes referred to as "compound (3)" in this specification), The catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0269] According to the production method (3), by using the catalyst, the versatile compound (30) and compound (9) are used as raw materials to form a carbon-silicon bond, thereby obtaining compound (3) as an organosilicon compound.

[0270] <Catalyst> The catalyst and its production method in the production method (3) are the same as the catalyst and its production method in the production method (1).

[0271] The catalyst used in the reaction step of the production method (3) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0272] The catalyst in production method (3) is preferably a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon. Use of such a catalyst allows compound (3) to be obtained more easily and in a higher yield.

[0273] <Compound (30)> The compound (30) is represented by the general formula (30). In the formula, l1 is the number of repetitions of the chain structure to which this symbol is attached, and is an integer of 2 or more. That is, compound (30) includes both oligomers and polymers. l1 is preferably 2 to 200. In particular, when compound (30) is a polymer, l1 is preferably 5 to 100, and more preferably 10 to 80. Production method (3) is extremely useful in that compound (30) which is a polymer can be used.

[0274] In the formula, l2 represents a group represented by the general formula "-C(=O)-R 32 is the number of groups represented by "-", and is 0 or 1. When l2 is 0, an example of compound (30) is polycarbonate. When l2 is 1, an example of compound (30) is polyester.

[0275] In the formula, R 31 is an alkylene group, and Z 11 The alkylene groups are the same as those in the above. R 31 The alkylene group in R is preferably an alkylene group having 3 to 12 carbon atoms, and more preferably an alkylene group having 2 to 8 carbon atoms. 31 Compound (30) in which is an alkylene group having 2 carbon atoms (i.e., an ethylene group), an alkylene group having 4 carbon atoms (i.e., a butylene group), or an alkylene group having 6 carbon atoms (i.e., a hexylene group) is easier to produce or obtain.

[0276] R 31 In the above formula, one or more methylene groups in the alkylene group may be substituted with an arylene group. Examples of the arylene group in which the methylene group is substituted include Z 11 Examples of the arylene group include the same arylene groups as those in the above formula. The arylene group is preferably an arylene group having 6 to 12 carbon atoms, and more preferably a phenylene group. R31 When two or more methylene groups in the alkylene group in the formula (I) are substituted with arylene groups, it is preferable that these substituted methylene groups are not adjacent to each other. For example, in the formula (I), two or more methylene groups are substituted with arylene groups. 31 An example of the formula is —C6H4—C(CH3)2—C6H4—.

[0277] R 31 When a methylene group in the alkylene group is substituted with an arylene group, the number of substitutions is 31 The number of carbon atoms is less than or equal to R 31 It is preferable that the number of carbon atoms is less than 1, and usually 1 or 2 is preferable.

[0278] l1 R 31 may be the same or different from each other. That is, l1 R 31 may be all the same, all different, or only some of them may be the same. For example, in terms of easier production or availability of compound (30), 31 are preferably all the same.

[0279] In the formula, R 32 is an alkylene group or an arylene group. R 32 The alkylene group in 11 The alkylene groups in R 32 The alkylene group in the formula (I) is preferably an alkylene group having 3 to 12 carbon atoms, and more preferably an alkylene group having 2 to 6 carbon atoms. R 32 As the arylene group in 11 The arylene groups in R 32 The arylene group in the formula (I) is preferably an arylene group having 6 to 12 carbon atoms.

[0280] If l2 is 1, then l1 R 32may be the same or different from each other. That is, l1 R 32 may be all the same, all different, or only some of them may be the same. For example, in terms of easier production or availability of compound (30), 32 are preferably all the same.

[0281] The terminal carboxy group (-C(=O)-OH) in the formula may form a salt. Here, when l2 is 0, the terminal carboxy group is a group represented by the general formula "-OR 31 - is a carboxyl group attached to the oxygen atom in "-", and when l2 is 1, R 32 is a carboxyl group bonded to Examples of the salts include alkali metal salts such as sodium salts, potassium salts, and lithium salts; and quaternary ammonium salts.

[0282] An example of a preferred compound (30) is a compound represented by the following general formula (30)-1

[0283] [ka] (In the formula, l 11 is an integer greater than or equal to 2; l 21 is 0 or 1; R 311 is an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group; 11 R 311 may be the same or different from each other; R 321 is an alkylene group having 2 to 6 carbon atoms or an arylene group having 6 to 12 carbon atoms, 21 If is 1, then l 11 R 321 may be the same or different from each other; In the formula, the terminal carboxy group may form a salt.) (sometimes referred to herein as "compound (30)-1").

[0284] In the formula, l 11 is the number of repetitions of the chain structure to which this symbol is attached, and is an integer of 2 or more, and may be in the same numerical range as l1.

[0285] In the formula, l 21 is represented by the general formula "-C(=O)-R 321 - is the number of groups represented by "-" and is 0 or 1. 21 An example of the compound (30)-1 when is 0 is polycarbonate. 21 When is 1, an example of the compound (30)-1 is a polyester.

[0286] In the formula, R 311 is an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group. Except for the fact that the number of carbon atoms is limited to 2 to 8, R 31 is the same as: l 11 R 311 may be the same or different from each other. 11 R 311 may all be the same, may all be different, or may only be partially the same.

[0287] In the formula, R 321 is an alkylene group having 2 to 6 carbon atoms or an arylene group having 6 to 12 carbon atoms. 321 The alkylene group having 2 to 6 carbon atoms in R is the same as R except that the number of carbon atoms is limited. 32 is the same as the alkylene group in R 321 The arylene group having 6 to 12 carbon atoms in the formula (I) is the same as R except that the number of carbon atoms is limited. 32 is the same as the arylene group in l 21 If is 1, then l11 R 321 may be the same or different from each other. 11 R 321 may all be the same, may all be different, or may only be partially the same.

[0288] The terminal carboxy group in the formula may form a salt, and the mode of forming the salt in this case is the same as the mode of forming the salt of the terminal carboxy group in general formula (30). For example, the terminal carboxy group in general formula (30)-1 is 21 When is 0, the general formula "-OR 311 - is a carboxyl group attached to the oxygen atom in l 21 If is 1, then R 321 is a carboxyl group bonded to

[0289] The compound (30) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0290] <Compound (9)> The compound (9) in the production method (3) is the same as the compound (9) in the production method (1).

[0291] A preferred compound (9) in the production method (3) is a compound represented by the following general formula (9)-1

[0292] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) that is, compound (9)-1.

[0293] More preferred compounds (9) in the production method (3) include the same as the more preferred compounds (9) in the production method (1).

[0294] The compound (9) used in the reaction step of the production method (3) may be one type or two or more types. When two or more types are used, the combination and ratio thereof can be arbitrarily selected depending on the purpose.

[0295] <Compound (3)> Compound (3) is the target product of production method (3) and is represented by the above general formula (3). In the formula, R 31 is R in general formula (30) 31 is the same as R 91 is R in general formula (9) 91 is the same as:

[0296] In the production method (3), compound (30)-1 is used as compound (30) and compound (9)-1 is used as compound (9), and thus compound (3) can be prepared, for example, by using a compound represented by the following general formula (3)-1

[0297] [ka] (In the formula, R 311 and R 911 is the same as above.) (sometimes referred to as "compound (3)-1" in this specification) can be suitably obtained.

[0298] When compound (30)-1 and compound (9)-1 are used in the reaction step of production method (3), the catalyst may be, for example, zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or a compound in which gold is supported on carbon.

[0299] <Other ingredients> In the reaction step of production method (3), a component other than compound (30), compound (9), or the catalyst may be used (the reaction may be carried out by adding another component) within a range that does not impair the effects of the present invention.

[0300] The other component used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0301] The other components can be selected arbitrarily depending on the purpose and are not particularly limited.

[0302] [solvent] Preferable examples of the other components include the same solvents as in the production method (1). By dissolving either or both of compound (30) and compound (9) in a solvent and carrying out the reaction, the yield of compound (3) can be increased. The solvent is preferably one that is unreactive with both compound (30) and compound (9).

[0303] As in the case of Production Method (1), preferred examples of the solvent in Production Method (3) include aromatic hydrocarbons such as toluene, benzene, o-xylene (1,2-dimethylbenzene), m-xylene (1,3-dimethylbenzene), and p-xylene (1,4-dimethylbenzene); cyclic ethers such as 1,4-dioxane and tetrahydrofuran (THF); and halogenated aromatic hydrocarbons such as benzotrifluoride.

[0304] The solvent used in the reaction step of the production method (3) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0305] <Reaction conditions> The reaction conditions in the reaction step of Production Method (3) (e.g., the amount of compound (9) used, the amount of the catalyst used, the amount of solvent used, the reaction temperature, the reaction time, the atmosphere, etc.) can be the same as the reaction conditions in the reaction step of Production Method (1) (particularly, the reaction conditions for producing Compound (1)), except that Compound (30) is used instead of Compound (10).

[0306] The reaction conditions in the reaction step of production method (3) may be adjusted appropriately depending on the value of l1 in general formula (30), i.e., the molecular size of compound (30). For example, as described above, when compound (30) is an oligomer or polymer, such as when l1 is 5 to 100, the reaction temperature may be either 80°C or higher or 100°C or higher, in order to increase the yield of compound (3). On the other hand, the reaction temperature may be 180°C or lower, in order to avoid excessive heating of the reaction solution and to increase the effect of suppressing the generation of impurities.

[0307] Similarly, when compound (30) is an oligomer or a polymer, such as when l1 is 5 to 100, the amount of compound (9) used may be 3 to 12 times by mass the amount of compound (10) used, in order to increase the ratio of the total number of reacted sites to the total number of reactive sites of compound (30) (i.e., the reaction rate) and to prevent excessive use of compound (9). Similarly, when compound (30) is an oligomer or a polymer, such as when l1 is 5 to 100, the amount of the catalyst used may be such that the amount of gold in the catalyst is 0.006 to 0.03 times by mass the amount of compound (10) used, in order to further increase the reaction rate of compound (30) and prevent excessive use of the catalyst. Similarly, when l1 is 5 to 100, for example, compound (30) is an oligomer or polymer, and a solvent is used, the amount of solvent used may be 1 to 4 L per kg of compound (10), in order to enhance the effect obtained by using the solvent and to prevent excessive use of the solvent.

[0308] In Production Method (3), after completion of the reaction step, compound (3) can be isolated by performing post-treatment, if necessary, using a known method, as in Production Method (1). The isolated compound (3) may be purified as in Production Method (1), or, after completion of the reaction step, compound (3) may be used for the intended purpose without being isolated after performing post-treatment, if necessary.

[0309] The structure of compound (3) can be confirmed by known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), and infrared spectroscopy (IR).

[0310] In production method (3), as in production method (1), after the reaction step, the catalyst used in the reaction step may be recovered, and the recovered catalyst may be used to carry out the reaction step again, a re-reaction step being carried out one or more times. The catalyst is solid, and after the reaction, contamination of compound (3) can be avoided. It can be easily recovered by filtering and washing, and can be reused repeatedly. Furthermore, even when the catalyst is reused in this way, compound (3) can be obtained at the same reaction rate and yield as when a non-recycled catalyst is used, and therefore production method (3) has excellent suitability for catalyst reuse.

[0311] In the production method (3), the catalyst can be reused (for example, washed and dried) in the same manner as in the production method (1).

[0312] In the production method (3), the re-reaction step may be the same as the reaction step, except that the recovered catalyst is used as the catalyst.

[0313] A preferred example of production method (3) is a production method in which compound (30) is compound (30)-1, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (3) is compound (3)-1 (sometimes referred to as “production method (3)-1” in this specification). That is, in the production method (3)-1, a compound represented by the following general formula (30)-1

[0314] [ka] (In the formula, l 11 is an integer greater than or equal to 2; l 21 is 0 or 1; R 311 is an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group; 11 R 311 may be the same or different from each other; R 321 is an alkylene group having 2 to 6 carbon atoms or an arylene group having 6 to 12 carbon atoms, 21 If is 1, then l 11 R 321 may be the same or different from each other; wherein the terminal carboxy group may form a salt.) (compound (30)-1), The following general formula (9)-1

[0315] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (3)-1

[0316] [ka] (In the formula, R 311 and R 911is the same as above.) The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0317] In the reaction step of the production method (3), R 31 and R 31 It is presumed that the bond between the two oxygen atoms bonded to and, more specifically, the carbon-oxygen (CO) bond, is broken by the action of the catalyst to generate a carbon radical (C·), which triggers the formation of a new carbon-silicon (C-Si) bond, thereby producing compound (3). In that the action of the catalyst generates the carbon radical (C·), which triggers the subsequent reaction to form a new carbon-silicon bond, production method (3) has something in common with production methods (1) and (2) and production methods (4) and (5) described below.

[0318] According to production method (3), by using the catalyst, compound (30) and compound (9) can be easily produced using them as raw materials. During this reaction, the carbon-oxygen (CO) bond in compound (30) is broken, and a new carbon-silicon (C-Si) bond is formed, which is a novel reaction not previously known. Furthermore, the catalyst can be easily recovered and reused repeatedly. Thus, the reaction of compound (30) with compound (9) in the presence of the catalyst to obtain compound (3) is extremely useful as a synthetic reaction for organosilicon compounds.

[0319] In particular, when compound (30) is a polymer with a large l1 value, many reactive sites (carbon-oxygen bonds) exist in one molecule of compound (30). According to production method (3), the desired reaction can be carried out at all or most of the reactive sites, resulting in the production of a large amount of compound (3). In this case, production method (3) is extremely important not only because it produces a large yield of compound (3), but also because it can decompose the polymeric compound (30) through a reaction. For example, polyester is produced in large quantities as a material for containers, clothing, etc., but after use, it becomes a large amount of waste, and its disposal has become a global problem. Therefore, attempts have been made to recycle used polyester, and the most desirable way to recycle polyester is through polyester decomposition.

[0320] As is well known, polyesters are produced by the dehydration condensation of dicarboxylic acids and diols. Decomposition of polyesters can be achieved by the reverse reaction, i.e., hydrolysis of esters. Conventionally, polyester hydrolysis has been carried out under alkaline conditions. However, in this case, the product obtained along with the starting diol is a dicarboxylic acid disalt (e.g., disodium dicarboxylate when sodium hydroxide is used as the alkali), which is unsuitable for use in the production of various materials, including polyesters. Specifically, the dicarboxylic acid disalt must be converted to a dicarboxylic acid by freeing the carboxyl groups forming the salt through acid treatment. This not only requires an additional step, but also produces a large amount of salt as a by-product. Alternatively, polyesters can be decomposed by hydrogenolysis. However, in this case, the product obtained along with the starting diol is a reduced form of the starting dicarboxylic acid, i.e., an undesired diol different from the starting material. This unintended diol is not necessarily useful as an industrial material, and on the other hand, in order to use it in the production of polyester, it needs to be converted into a dicarboxylic acid by oxidation, which requires an additional process. Thus, conventional polyester decomposition has had problems, such as producing materials that are not necessarily useful as they are and requiring an additional process to produce polyester.

[0321] In contrast, according to production method (3), dicarboxylic acid bissilyl esters are obtained by cleavage of the carbon-oxygen bond in compound (30) under mild conditions, which can be converted to dicarboxylic acids, which are starting materials for polyester production, by hydrolysis under neutral conditions without requiring special reaction conditions. Furthermore, compound (3) obtained at the same time is an organosilicon compound, which is useful as a raw material or intermediate for pharmaceuticals and agricultural chemicals, and is also useful as a functional material and a raw material or intermediate for functional materials, and is an important compound group. Thus, in production method (3), by using polyester as compound (30), polyester can be easily decomposed, and dicarboxylic acid, which is a starting material for polyester production, can be easily produced. In addition, industrially important organosilicon compounds can be produced in large quantities as compound (3), making production method (3) extremely useful.

[0322] Furthermore, compound (30), whether polymeric or not, is relatively stable and can be produced simply and easily from an alcohol (diol). Compound (30) is readily available as a variety of commercially available products. Compound (30) is also relatively inexpensive. Compound (9) is also easy to produce or obtain, is relatively stable, and is relatively inexpensive. Furthermore, because compound (30) and compound (9) are relatively stable, compound (3), which could not be produced by conventional methods, can be easily produced.

[0323] Thus, the production method (3) is extremely effective in terms of usefulness and versatility.

[0324] <<Manufacturing method (4)>> A method for producing a compound according to one embodiment of the present invention (sometimes referred to herein as "production method (4)") comprises reacting a compound represented by the following general formula (40):

[0325] [ka] (In the formula, R 41 and R 42 are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and R 41 and R 42 When both are the alkyl groups, R 41 and R 42 may be bonded to each other to form a ring; R 43 is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group; R 44is an alkyl group, an aryl group, or an aralkyl group.) (sometimes referred to as "compound (40)" in this specification), The following general formula (9)

[0326] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) (i.e., compound (9)), in the presence of a catalyst to form a compound represented by the following general formula (4):

[0327] [ka] (In the formula, R 41 , R 42 , R 43 and R 91 is the same as above.) (sometimes referred to as "compound (4)" in this specification), The catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0328] According to the production method (4), by using the catalyst, the versatile compound (40) and compound (9) are used as raw materials to form a carbon-silicon bond, thereby obtaining compound (4) as an organosilicon compound.

[0329] <Catalyst> The catalyst and its production method in the production method (4) are the same as the catalyst and its production method in the production method (1).

[0330] The catalyst used in the reaction step of the production method (4) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0331] The catalyst in production method (4) is preferably a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon. Use of such a catalyst allows compound (4) to be obtained more easily and in a higher yield.

[0332] <Compound (40)> The compound (40) is represented by the general formula (40). In the formula, R 41 and R 42 are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group. R 41 and R 42 The alkyl group, aryl group and aralkyl group in R 11 and R 12 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above.

[0333] R 41 and R 42 When both are the alkyl groups, R 41 and R 42 are mutually bonded to each other, and these (R 41 and R 42 ) may form a ring together with the carbon atom to which it is attached. At this time, R 41 and R 42 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring.

[0334] R 41 and R 42 are preferably each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.

[0335] In the formula, R43 is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group. R 43 The alkyl group, aryl group and aralkyl group in R 11 and R 12 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above.

[0336] R 43 In the trialkylsilyl group in the above formula, the three alkyl groups bonded to the silicon atom may be linear, branched, or cyclic, and if cyclic, may be monocyclic or polycyclic. The three alkyl groups bonded to the silicon atom may be the same or different, or only some (two) of them may be the same. The combination of these three alkyl groups is not particularly limited. The three alkyl groups bonded to the silicon atom include R 11 and R 12 Examples of the alkyl group include the same as those in the alkyl group. The three alkyl groups bonded to the silicon atom are preferably each independently a chain (straight chain or branched chain), and more preferably each independently a chain alkyl group having 1 to 4 carbon atoms.

[0337] R 43 Preferred examples of the trialkylsilyl group in the above formula (I) include a trimethylsilyl group, a dimethylethylsilyl group, a methyldiethylsilyl group, a triethylsilyl group, a dimethyl-n-propylsilyl group, a methyldi(n-propyl)silyl group, a dimethyl-tert-butylsilyl group, and a methyldi(tert-butyl)silyl group.

[0338] R 43In the dialkylarylsilyl group in the above formula, the two alkyl groups bonded to the silicon atom may be linear, branched, or cyclic, and if cyclic, may be monocyclic or polycyclic. The two alkyl groups bonded to the silicon atom may be the same or different, and the combination of these two alkyl groups is not particularly limited. The two alkyl groups bonded to the silicon atom include the same alkyl groups as those bonded to the silicon atom in the trialkylsilyl group. These two alkyl groups are preferably each independently a chain (linear or branched), and more preferably each independently a chain alkyl group having 1 to 4 carbon atoms. The aryl group bonded to the silicon atom includes R 11 and R 12 The aryl group preferably has 6 to 8 carbon atoms, and the aryl group is preferably a phenyl group, a 2-methylphenyl group (o-tolyl group), a 3-methylphenyl group (m-tolyl group), a 4-methylphenyl group (p-tolyl group), or a dimethylphenyl group (xylyl group).

[0339] R 43 Preferred examples of the dialkylarylsilyl group in the above formula (1) include a dimethylphenylsilyl group, a dimethyl(2-methylphenyl)silyl group (also known as a dimethyl o-tolylsilyl group), a dimethyl(3-methylphenyl)silyl group (also known as a dimethyl m-tolylsilyl group), a dimethyl(4-methylphenyl)silyl group (also known as a dimethyl p-tolylsilyl group), and a dimethyl(dimethylphenyl) group (dimethylxylylsilyl group).

[0340] R 43 is preferably an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms.

[0341] In the formula, R 44 is an alkyl group, an aryl group, or an aralkyl group. R 44 The alkyl group, aryl group and aralkyl group in R 43 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above.

[0342] R 44 is preferably an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.

[0343] An example of a preferred compound (40) is a compound represented by the following general formula (40)-1

[0344] [ka] (In the formula, R 411 and R 421 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and R 411 and R 421 When both are the alkyl groups, R 411 and R 421 may be bonded to each other to form a ring; R 431 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms; R 441 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.) (sometimes referred to as "compound (40)-1" in this specification).

[0345] In the formula, R 411 and R 421are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms. R 411 and R 421 In the above, the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, and the aralkyl group having 7 to 13 carbon atoms include R 41 and R 42 Examples of the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, and the aralkyl group having 7 to 13 carbon atoms are the same as those mentioned above.

[0346] R 411 and R 421 When both are the alkyl groups, R 411 and R 421 are mutually bonded to each other, and these (R 411 and R 421 ) may form a ring together with the carbon atom to which it is attached. At this time, R 411 and R 421 The embodiment in which the groups are bonded to each other to form a ring is the same as that of Z 11 and R 11 are bonded to each other to form a ring.

[0347] In the formula, R 431 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms, and these are R 43 The alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, the trialkylsilyl group having 3 to 8 carbon atoms, or the dialkylarylsilyl group having 8 to 10 carbon atoms in the above formula (I) is the same as the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, the aralkyl group having 7 to 13 carbon atoms, the trialkylsilyl group having 3 to 8 carbon atoms, or the dialkylarylsilyl group having 8 to 10 carbon atoms.

[0348] In the formula, R 441 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and these are represented by R 43The alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the aralkyl group having 7 to 13 carbon atoms in the above formula (I) is the same as the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the aralkyl group having 7 to 13 carbon atoms.

[0349] The compound (40) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0350] <Compound (9)> The compound (9) in the production method (4) is the same as the compound (9) in the production method (1).

[0351] A preferred compound (9) in the production method (4) is a compound represented by the following general formula (9)-1

[0352] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) that is, compound (9)-1.

[0353] More preferred compounds (9) in the production method (4) include the same as the more preferred compounds (9) in the production method (1).

[0354] The compound (9) used in the reaction step of the production method (4) may be one type or two or more types. When two or more types are used, the combination and ratio thereof can be arbitrarily selected depending on the purpose.

[0355] <Compound (4)> Compound (4) is the target product of production method (4) and is represented by the above general formula (4). In the formula, R 41 , R42 and R 43 is R in general formula (40) 41 , R 42 and R 43 is the same as R 91 is R in general formula (9) 91 is the same as:

[0356] In the production method (4), compound (40)-1 is used as compound (40) and compound (9)-1 is used as compound (9), and thus compound (4) can be obtained by using, for example, a compound represented by the following general formula (4)-1

[0357] [ka] (In the formula, R 411 , R 421 , R 431 and R 911 is the same as above.) (sometimes referred to as "compound (4)-1" in this specification) can be suitably obtained.

[0358] When compound (40)-1 and compound (9)-1 are used in the reaction step of production method (4), the catalyst may be, for example, zirconium oxide, titanium oxide, iron trioxide, iron trioxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or a compound in which gold is supported on carbon.

[0359] <Other ingredients> In the reaction step of production method (4), a component other than compound (40), compound (9), or the catalyst may be used (the reaction may be carried out by adding another component) within a range that does not impair the effects of the present invention.

[0360] The other component used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0361] The other components can be selected arbitrarily depending on the purpose and are not particularly limited.

[0362] [solvent] A preferred example of the other component is the same solvent as in the production method (1). By dissolving either or both of compound (40) and compound (9) in a solvent and carrying out the reaction, the yield of compound (4) can be increased. The solvent is preferably one that is unreactive with both compound (40) and compound (9).

[0363] As in the case of Production Method (1), preferred examples of the solvent in Production Method (4) include aromatic hydrocarbons such as toluene, benzene, o-xylene (1,2-dimethylbenzene), m-xylene (1,3-dimethylbenzene), and p-xylene (1,4-dimethylbenzene); cyclic ethers such as 1,4-dioxane and tetrahydrofuran (THF); and halogenated aromatic hydrocarbons such as benzotrifluoride.

[0364] The solvent used in the reaction step of the production method (4) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0365] <Reaction conditions> The reaction conditions in the reaction step of Production Method (4) (e.g., the amount of compound (9) used, the amount of the catalyst used, the amount of solvent used, the reaction temperature, the reaction time, the atmosphere, etc.) can be the same as the reaction conditions in the reaction step of Production Method (1) (particularly, the reaction conditions for producing Compound (1)), except that Compound (40) is used instead of Compound (10).

[0366] In the production method (4), after completion of the reaction step, compound (4) can be isolated by performing post-treatment, if necessary, using a known method, as in the production method (1). The isolated compound (4) may be purified as in the production method (1), or after completion of the reaction step, compound (4) may be used for the intended purpose without being isolated, after performing post-treatment, if necessary.

[0367] The structure of compound (4) can be confirmed by known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), and infrared spectroscopy (IR).

[0368] In Production Method (4), as in Production Method (1), after the reaction step, the catalyst used in the reaction step may be recovered, and the recovered catalyst may be used to carry out the reaction step again, a re-reaction step being carried out one or more times. The catalyst is solid, and after the reaction, contamination of compound (4) can be avoided. It can be easily recovered by filtering and washing, and can be reused repeatedly. Furthermore, even when the catalyst is reused in this way, compound (4) can be obtained at the same reaction rate and yield as when a non-recycled catalyst is used, and therefore Production Method (4) has excellent suitability for catalyst reuse.

[0369] In the production method (4), the catalyst can be reused (for example, washed and dried) in the same manner as in the production method (1).

[0370] In the production method (4), the re-reaction step may be the same as the reaction step, except that the recovered catalyst is used as the catalyst.

[0371] A preferred example of the production method (4) is a production method (sometimes referred to as "production method (4)-1" in this specification) in which compound (40) is compound (40)-1, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (4) is compound (4)-1. That is, the production method (4)-1 is a production method in which compound (40) is compound (40)-1,

[0372] [ka] (In the formula, R 411 and R 421 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and R 411 and R 421 When both are the alkyl groups, R 411 and R 421 may be bonded to each other to form a ring; R 431 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms; R 441 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms (compound (40)-1), The following general formula (9)-1

[0373] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (4)-1

[0374] [ka] (In the formula, R 411 , R 421 , R 431 and R 911 is the same as above.) The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0375] In the reaction step of the production method (4), R 41 and R 42 It is presumed that the carbon-oxygen (CO) bond between the carbon atom to which R is bonded and the oxygen atom to which the carbon atom is bonded is broken by the action of the catalyst, generating a carbon radical (C·), which then triggers the formation of a new carbon-silicon (C-Si) bond, producing compound (4). 41 and R 42 Therefore, the reaction after the carbon radical (C·) is generated differs from that in production methods (1) to (3), and it is presumed that compound (4), which is a different system from compounds (1) to (3), is generated. However, production method (4) has something in common with production methods (1) to (3) and production method (5) described below in that the carbon radical (C·) is generated by the action of the catalyst, which triggers the subsequent reaction to form a new carbon-silicon bond.

[0376] According to production method (4), by using the catalyst, compound (40) and compound (9) can be easily produced using them as raw materials. During this process, the carbon-oxygen (CO) bond in compound (40) is broken, and a new carbon-silicon (C-Si) bond is formed, which is a novel reaction not previously known. Furthermore, the catalyst can be easily recovered and reused repeatedly. Thus, the reaction of compound (40) with compound (9) in the presence of the catalyst to obtain compound (4) is extremely useful as a synthetic reaction for organosilicon compounds.

[0377] Furthermore, compound (40) is relatively stable and can be produced simply and easily from an alcohol. Compound (40) is readily available as a commercially available product, and is relatively inexpensive. Compound (9) is also easy to produce or obtain, is relatively stable, and is relatively inexpensive. Furthermore, because compound (40) and compound (9) are relatively stable, compound (4), which could not be produced by conventional methods, can be easily produced. Thus, production method (4) exhibits significant advantages in terms of usefulness and versatility.

[0378] <<Manufacturing method (5)>> A method for producing a compound according to one embodiment of the present invention (sometimes referred to herein as "production method (5)") comprises reacting a compound represented by the following general formula (50):

[0379] [ka] (In the formula, R 51 is a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; R 52 is an alkyl group, an aryl group, or an aralkyl group.) (sometimes referred to as "compound (50)" in this specification), The following general formula (9)

[0380] [ka] (In the formula, R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.) (i.e., compound (9)), in the presence of a catalyst to form a compound represented by the following general formula (5):

[0381] [ka] (In the formula, R 51 and R 91 is the same as above.) (sometimes referred to as "compound (5)" in this specification), The catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0382] According to the production method (5), by using the catalyst, the versatile compound (50) and compound (9) are used as raw materials to form a carbon-silicon bond, thereby obtaining compound (5) as an organosilicon compound.

[0383] <Catalyst> The catalyst and its production method in the production method (5) are the same as the catalyst and its production method in the production method (1).

[0384] The catalyst used in the reaction step of the production method (5) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0385] The catalyst in production method (5) is preferably a compound in which gold is supported on zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, chromium trioxide, or carbon. Use of such a catalyst allows compound (5) to be obtained more easily and in a higher yield.

[0386] <Compound (50)> The compound (50) is represented by the general formula (50). In the formula, R 51 is a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group. R 51 The alkyl group, aryl group and aralkyl group in R 11 and R 12 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above. R 51 is preferably a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.

[0387] In the formula, R 52 is an alkyl group, an aryl group, or an aralkyl group. R 52 The alkyl group, aryl group and aralkyl group in R 11 and R 12 Examples of the alkyl group, aryl group and aralkyl group are the same as those in the above. R 52 is preferably an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.

[0388] An example of a preferred compound (50) is a compound represented by the following general formula (50)-1

[0389] [ka] (In the formula, R 511 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; R 521 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms.) (sometimes referred to as "compound (50)-1" in this specification).

[0390] In the formula, R511 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms. R 511 In the above, the alkyl group having 1 to 12 carbon atoms is R 51 Examples include the same alkyl groups having 1 to 12 carbon atoms as those mentioned above.

[0391] In the formula, R 521 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and these are represented by R 52 The alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the aralkyl group having 7 to 13 carbon atoms in the above formula (I) is the same as the alkyl group having 1 to 8 carbon atoms, the aryl group having 6 to 12 carbon atoms, or the aralkyl group having 7 to 13 carbon atoms.

[0392] The compound (50) used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0393] <Compound (9)> The compound (9) in the production method (5) is the same as the compound (9) in the production method (1).

[0394] A preferred compound (9) in the production method (5) is a compound represented by the following general formula (9)-1

[0395] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) that is, compound (9)-1.

[0396] More preferred compounds (9) in the production method (5) include the same as the more preferred compounds (9) in the production method (1).

[0397] The compound (9) used in the reaction step of the production method (5) may be one type or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0398] <Compound (5)> Compound (5) is the target product of production method (5) and is represented by the above general formula (5). In the formula, R 51 is R in general formula (50) 51 is the same as R 91 is R in general formula (9) 91 is the same as:

[0399] In the production method (5), compound (50)-1 is used as compound (50) and compound (9)-1 is used as compound (9), and thus compound (5) can be obtained by using, for example, a compound represented by the following general formula (5)-1:

[0400] [ka] (In the formula, R 511 and R 911 is the same as above.) (sometimes referred to as "compound (5)-1" in this specification) can be suitably obtained.

[0401] When compound (50)-1 and compound (9)-1 are used in the reaction step of production method (5), the catalyst may be, for example, zirconium oxide, titanium oxide, iron trioxide, iron tetraoxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or a compound in which gold is supported on carbon.

[0402] <Other ingredients> In the reaction step of production method (5), a component other than compound (50), compound (9), or the catalyst may be used (the reaction may be carried out by adding another component) within a range that does not impair the effects of the present invention.

[0403] The other component used in the reaction step may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0404] The other components can be selected arbitrarily depending on the purpose and are not particularly limited.

[0405] [solvent] Preferable examples of the other components include the same solvents as in the production method (1). By dissolving either or both of compound (50) and compound (9) in a solvent and carrying out the reaction, the yield of compound (5) can be increased. The solvent is preferably one that is unreactive with both compound (50) and compound (9).

[0406] As in the case of Production Method (1), preferred examples of the solvent in Production Method (5) include aromatic hydrocarbons such as toluene, benzene, o-xylene (1,2-dimethylbenzene), m-xylene (1,3-dimethylbenzene), and p-xylene (1,4-dimethylbenzene); cyclic ethers such as 1,4-dioxane and tetrahydrofuran (THF); and halogenated aromatic hydrocarbons such as benzotrifluoride.

[0407] The solvent used in the reaction step of the production method (5) may be one type only, or two or more types. When two or more types are used, the combination and ratio thereof can be selected arbitrarily depending on the purpose.

[0408] <Reaction conditions> The reaction conditions in the reaction step of Production Method (5) (e.g., the amount of compound (9) used, the amount of the catalyst used, the amount of solvent used, the reaction temperature, the reaction time, the atmosphere, etc.) can be the same as the reaction conditions in the reaction step of Production Method (1) (particularly, the reaction conditions for producing Compound (1)), except that Compound (50) is used instead of Compound (10).

[0409] In the production method (5), after completion of the reaction step, compound (5) can be isolated by performing post-treatment, if necessary, using a known method, as in the production method (1). The isolated compound (5) may be purified as in the production method (1), or, after completion of the reaction step, compound (5) may be used for the intended purpose without being isolated after performing post-treatment, if necessary.

[0410] The structure of compound (5) can be confirmed by known techniques such as nuclear magnetic resonance (NMR) spectroscopy, mass spectroscopy (MS), and infrared spectroscopy (IR).

[0411] In Production Method (5), as in Production Method (1), after the reaction step, the catalyst used in the reaction step may be recovered, and the recovered catalyst may be used to carry out the reaction step again, a re-reaction step being carried out one or more times. The catalyst is solid, and after the reaction, contamination of compound (5) can be avoided. It can be easily recovered by filtering and washing, and can be reused repeatedly. Furthermore, even when the catalyst is reused in this way, compound (5) can be obtained at the same reaction rate and yield as when a non-recycled catalyst is used, and therefore Production Method (5) has excellent suitability for catalyst reuse.

[0412] In the production method (5), the catalyst can be reused (for example, washed and dried) in the same manner as in the production method (1).

[0413] In the production method (5), the re-reaction step may be the same as the reaction step, except that the recovered catalyst is used as the catalyst.

[0414] A preferred example of the production method (5) is a production method (sometimes referred to as "production method (5)-1" in this specification) in which compound (50) is compound (50)-1, compound (9) is compound (9)-1, the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon, and compound (5) is compound (5)-1. That is, the production method (5)-1 is a method in which compound (50)-1 is represented by the following general formula (50)-1

[0415] [ka] (In the formula, R 511 represents a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; R 521 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms) (compound (50)-1), The following general formula (9)-1

[0416] [ka] (In the formula, R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different from each other.) (compound (9)-1), in the presence of a catalyst to form a compound represented by the following general formula (5)-1

[0417] [ka] (In the formula, R 511 and R 911 is the same as above.) The catalyst may be a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

[0418] In the reaction step of the production method (5), R 51 It is presumed that the carbon-oxygen (CO) bond between the carbon atom to which the cyclopropyl group is bonded and the oxygen atom to which the carbon atom is bonded is cleaved by the action of the catalyst, generating a carbon radical (C·). This reaction triggers the formation of a new carbon-silicon (C-Si) bond, resulting in the production of compound (5). However, compound (50) contains the cyclopropyl group, and therefore the reaction that follows the generation of the carbon radical (C·) differs from that in production methods (1) to (3), resulting in the production of compound (5), which is a different type of compound from compounds (1) to (3). However, production method (5) shares a commonality with production methods (1) to (4) in that the action of the catalyst generates the carbon radical (C·), which triggers the subsequent reaction that leads to the formation of a new carbon-silicon bond.

[0419] According to production method (5), compound (5) can be easily produced using compound (50) and compound (9) as raw materials by using the catalyst. During this process, the carbon-oxygen (CO) bond in compound (50) is broken, and a new carbon-silicon (C-Si) bond is formed, which is a novel reaction not previously known. Furthermore, the catalyst can be easily recovered and reused repeatedly. Thus, the reaction of compound (50) with compound (9) in the presence of the catalyst to obtain compound (5) is extremely useful as a synthetic reaction for organosilicon compounds.

[0420] Furthermore, compound (50) is relatively stable and can be produced simply and easily from an alcohol. Compound (50) is readily available as a variety of commercially available products. Compound (50) is also relatively inexpensive. Compound (9) is also easily produced or readily available, relatively stable, and relatively inexpensive. Furthermore, because compound (50) and compound (9) are relatively stable, compound (5), which could not be produced by conventional methods, can be easily produced. Thus, production method (5) exhibits significant advantages in terms of usefulness and versatility.

[0421] ◎Compound <<Compound (1A)>> The compound according to one embodiment of the present invention is represented by the following general formula (1):

[0422] [ka] (In the formula, n 10 is an integer greater than or equal to 1; R 11 and R 12 are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 10 If is 2 or more, n 10 R 11 may be the same or different, and n 10 R 12 may be the same or different from each other; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and is represented by the general formula "-SiR 91 Three R's in "3" 91 may be the same or different, and n 10 If is 2 or more, n 10 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11 When is the hydrocarbon group which may have a substituent, Z 11 and R 11 may be bonded to each other to form a ring) (provided that the compound represented by the following formula

[0423] [ka] ) is excluded. The compound of this embodiment is the compound (1) described in the above production method (1), excluding the above-mentioned known compound, and may be referred to as "compound (1A)" in this specification. That is, compound (1A) is included in compound (1). Compound (1A) can be produced by production method (1).

[0424] An example of a preferred compound (1A) is a compound represented by the following general formula (1)-01

[0425] [ka] (In the formula, n 010 is an integer greater than or equal to 1; R 011 and R 012 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 011 and R 012 at least one of is a hydrogen atom; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and is represented by the general formula "-SiR 911 Three R's in "3" 911 may be the same or different from each other; n 010 If is 2 or more, n 010 R011 may be the same or different, and n 010 R 012 may be the same or different, and n 010 The general formula -SiR 911 The groups represented by "3" may be the same or different from each other; Z 011 represents a hydrocarbon group having 3 to 14 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 011 When Z is the hydrocarbon group having 3 to 14 carbon atoms which may have a substituent, 011 and R 011 may be bonded to each other to form a ring (excluding the known compounds). In this specification, the compound of this embodiment may be referred to as "compound (1A)-01." That is, compound (1A)-01 is included in compound (1)-01.

[0426] A more preferred example of the compound (1A) is a compound represented by the following general formula (1)-1

[0427] [ka] (In the formula, R 111 and R 121 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 111 and R 121 at least one of is a hydrogen atom; Z 111represents an alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 111 When is the alkyl group having 1 to 7 carbon atoms, Z 111 and R 111 may be bonded to each other to form a ring; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and three R 911 may be the same or different.) (excluding the known compounds). In this specification, the compound of this embodiment may be referred to as "compound (1A)-1." That is, compound (1A)-1 is included in compound (1)-1.

[0428] Other examples of more preferred compounds (1A) include compounds represented by the following general formula (1)-2

[0429] [ka] (In the formula, R 112 and R 122 are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R 112 and R 122 At least one of R is a hydrogen atom, and two R 112 may be the same or different, and two R 122may be the same or different from each other; Z 112 represents an alkylene group, alkenylene group, or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 112 When is the alkyl group having 1 to 7 carbon atoms, Z 112 and R 112 may be bonded to each other to form a ring; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) that is, compound (1)-2.

[0430] Compound (1) including compound (1A), compound (1)-1 including compound (1A)-1, and compound (1)-2 have already been described in detail, and therefore further detailed description of compound (1A), compound (1A)-1, and compound (1)-2 will be omitted here.

[0431] <<Compound (1')>> The compound according to one embodiment of the present invention is represented by the following general formula (1'):

[0432] [ka] (In the formula, n 11 and n 12 are each independently an integer of 1 or greater; R 11 and R 12are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R 11 and R 12 At least one of is a hydrogen atom, and n 11 If is 2 or more, n 11 R 11 may be the same or different, and n 11 R 12 may be the same or different, and n 12 If is 2 or more, n 12 R 11 may be the same or different, and n 12 R 12 may be the same or different from each other; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and is represented by the general formula "-SiR 91 Three R's in "3" 91 may be the same or different, and n 11 If is 2 or more, n 11 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; Z 11 is a hydrocarbon group which may have a substituent, and R 11 When is the hydrocarbon group which may have a substituent, Z 11 and R 11 may be bonded to each other to form a ring; X 11 is represented by the following general formula (101):

[0433] [ka] (In the formula, R 13 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group; a bond marked with an * is X 11is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102):

[0434] [ka] (In the formula, R 14 is an alkyl group, an aryl group, or an aralkyl group; a bond marked with an * is X 11 is formed with respect to the carbon atom to which n is bonded. 12 If is 2 or more, n 12 X's 11 may be the same or different. The compound of this embodiment is the compound (1') explained in the above production method (1). Compound (1') can be produced by production method (1).

[0435] An example of a preferred compound (1') is a compound represented by the following general formula (1')-01

[0436] [ka] (In the formula, n 011 and n 012 are each independently an integer of 1 or more, provided that n 011 +n 012 =n 010 (≥2); n 010 , R 011 , R 012 , Z 011 , X 011 and R 91 is the same as above, and the general formula "-SiR 911 Three R's in "3" 911 may be the same or different: n 011 If is 2 or more, n 011 R 011 may be the same or different, and n 011 R 012may be the same or different, and n 011 The general formula -SiR 91 The groups represented by "3" may be the same or different from each other; n 012 If is 2 or more, n 012 R 011 may be the same or different, and n 012 R 012 may be the same or different, and n 012 X's 011 may be the same or different. The compound of this embodiment is compound (1')-01 explained in the above production method (1).

[0437] Compound (1') and compound (1')-01 have already been described in detail, so further detailed description thereof will be omitted here.

[0438] <<Compound (2)>> The compound according to one embodiment of the present invention is represented by the following general formula (2):

[0439] [ka] (In the formula, Z 21 represents a hydrocarbon group which may have a substituent, and a carbon atom in the hydrocarbon group may be substituted with a nitrogen atom together with a hydrogen atom bonded to the carbon atom; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different. The compound of this embodiment is the compound (2) explained in the above production method (2). Compound (2) can be produced by production method (2).

[0440] An example of a preferred compound (2) is a compound represented by the following general formula (2)-1

[0441] [ka] (wherein m1 is an integer of 1 to 5; R 211 and R 212 are each independently a hydrogen atom, an alkyl group of 1 to 7 carbon atoms which may have a substituent, an alkenyl group of 2 to 7 carbon atoms which may have a substituent, or an aryl group of 6 to 10 carbon atoms which may have a substituent, and the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group of 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group of 1 to 3 carbon atoms, an acyloxy group of 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group, and when m1 is 2 or more, 211 may be the same or different, and m R 212 may be the same or different, and R 211 and R 212 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 211 and R 212 may be bonded to each other to form a ring, m1 is 2 or more, and R 211 Comrades or R 212 When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R 211 R 212 may be bonded to each other to form a ring, and R 211 and R 212 When either or both of R 211 and R 212may be replaced with a nitrogen atom, together with the hydrogen atom attached to said carbon atom; m2 is 0 or 1; R 213 and R 214 each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R 213 and R 214 is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R 213 and R 214 may be bonded to each other to form a ring; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) (excluding the known compounds). The compound of this embodiment is the compound (2)-1 explained in the above production method (2).

[0442] Compound (2) and compound (2)-1 have already been described in detail, so further detailed description thereof will be omitted here.

[0443] <<Compound (3)>> The compound according to one embodiment of the present invention is represented by the following general formula (3):

[0444] [ka] (In the formula, R 31 represents an alkylene group, and one or more methylene groups in the alkylene group may be substituted with an arylene group; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R 91 may be the same or different from each other.)

[0445] [ka] ) is excluded. The compound of this embodiment is the compound (3) described in the above production method (3), excluding the above-mentioned known compound, and may be referred to as "compound (3A)" in this specification. In other words, compound (3A) is included in compound (3). Compound (3A) can be produced by production method (3).

[0446] An example of a preferred compound (3A) is a compound represented by the following general formula (3)-1

[0447] [ka] (In the formula, R 311 represents an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R 911 may be the same or different.) (excluding the known compounds). In this specification, the compound of this embodiment may be referred to as "compound (3A)-1." That is, compound (3A)-1 is included in compound (3)-1.

[0448] Compound (3) containing compound (3A) and compound (3)-1 containing compound (3A)-1 have already been described in detail, so further detailed description of compound (3A) and compound (3A)-1 will be omitted here.

[0449] <<Compound (4)>> The compound according to one embodiment of the present invention is represented by the following general formula (4):

[0450] [ka] (In the formula, R 41 and R 42 are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and R 41 and R 42 When both are the alkyl groups, R 41 and R 42 may be bonded to each other to form a ring; R 43 is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group; R 91 is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and three R 91 may be the same or different. The compound of this embodiment is the compound (4) explained in the above production method (4). Compound (4) can be produced by production method (4).

[0451] An example of a preferred compound (4) is a compound represented by the following general formula (4)-1

[0452] [ka] (In the formula, R 411 and R 421 are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms, and R 411 and R 421 When both are the alkyl groups, R 411 and R 421 may be bonded to each other to form a ring; R 431 is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms; R 911 is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and three R 911 may be the same or different. The compound of this embodiment is compound (4)-1 explained in the above production method (4).

[0453] Compound (4) and compound (4)-1 have already been described in detail, so further detailed description thereof will be omitted here. [Example]

[0454] The present invention will be described in more detail below with reference to specific examples, although the present invention is not limited to the examples shown below.

[0455] The yields of compounds (1) to (5) shown in the following examples are all based on the amounts of compounds (10) to (50) used. The yield of compound (3) is calculated based on the theoretical amount of the moiety considered to be derived from the diol in compound (30).

[0456] [Manufacturing Example 1] <<Production of Compound (Au / ZrO2)>> A compound in which gold is supported on zirconium oxide (Au / ZrO2) was produced in accordance with a conventional method using the following procedure. Specifically, tetrachloroauric acid (III) and water were mixed, and while stirring at 70°C, 0.1 M aqueous sodium hydroxide solution was added dropwise to obtain an aqueous solution with a pH of 4. Zirconium oxide (ZrO2) was then added to this solution, and 0.1 M aqueous sodium hydroxide solution was then added dropwise to obtain an aqueous dispersion with a pH of 7. The zirconium oxide used was "JRC-ZRO-7" distributed by the Catalysis Society of Japan. The aqueous dispersion was then stirred at 70°C for 1 hour. The insoluble matter was then removed by centrifugation, washed with ion-exchanged water, and dried overnight at 80°C. The dried product was then calcined at 300°C for 1 hour, and the calcined product was then hydrogen-reduced at 200°C for 1 hour. This yielded the compound (Au / ZrO2).

[0457] When the resulting compound (Au / ZrO2) was observed using a high-angle annular dark-field scanning transmission electron microscope (HAADF-STEM), it was confirmed that numerous gold particles with a particle diameter of 2.7±0.9 nm were supported on the zirconium oxide. In this compound (Au / ZrO2), the ratio of the mass of gold to the mass of zirconium oxide (amount of supported gold) was 1 mass%.

[0458] [Manufacturing Example 2] <<Production of Compound (Au / TiO2)>> A compound (Au / TiO2) was obtained in the same manner as in Production Example 1, except that titanium oxide (TiO2) was used instead of zirconium oxide. The titanium oxide used was "JRC-TIO-15" distributed by the Catalysis Society of Japan. The fact that the compound (Au / TiO2) was obtained was confirmed by the same method as in Example 1. In this compound (Au / TiO2), the ratio of the mass of gold to the mass of titanium oxide (amount of supported gold) was 1 mass%.

[0459] [Manufacturing Example 3] <<Production of Compound (Au / C)>> A compound (Au / C) was obtained in the same manner as in Production Example 1, except that carbon (C, carbon black, "Ketjenblack EC300J" manufactured by Lion Specialty Chemicals) was used instead of zirconium oxide. The fact that the compound (Au / C) was obtained was confirmed in the same manner as in Example 1. In this compound (Au / C), the ratio of the mass of gold to the mass of carbon (amount of supported gold) was 1 mass %.

[0460] [Manufacturing Example 4] <<Production of Compound (Au / Fe2O3)>> A compound (Au / Fe2O3) was obtained in the same manner as in Production Example 1, except that diiron trioxide (Fe2O3, manufactured by Wako Pure Chemical Industries, Ltd.) was used instead of zirconium oxide. The fact that the compound (Au / Fe2O3) was obtained was confirmed in the same manner as in Example 1. In this compound (Au / Fe2O3), the ratio of the mass of gold to the mass of diiron trioxide (amount of supported gold) was 1 mass %.

[0461] [Manufacturing Example 5] <<Production of Compound (Au / ZrP2O7)>> The compound (Au / ZrP2O7) was produced with reference to the method described in the non-patent document "M. Machida et al., ACS Catal., 2015, 5, 1986-1994." The fact that the compound (Au / ZrP2O7) was obtained was confirmed by the same method as in Example 1. In this compound (Au / ZrP2O7), the ratio of the mass of gold to the mass of zirconium pyrophosphate (amount of supported gold) was 1 mass %.

[0462] [Manufacturing Example 6] <<Production of Compound (Au / Al2O3)>> A compound (Au / Al2O3) was obtained in the same manner as in Production Example 1, except that aluminum oxide (Al2O3, "AKP-G015" manufactured by Sumitomo Chemical Co., Ltd.) was used instead of zirconium oxide. The fact that the compound (Au / Al2O3) was obtained was confirmed in the same manner as in Example 1. In this compound (Au / Al2O3), the ratio of the mass of gold to the mass of aluminum oxide (amount of supported gold) was 1 mass %.

[0463] <<Production of Compound (1) (Consideration of the Type of Catalyst)>> [Example 1] Under an argon gas atmosphere, compound (10)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO) obtained above (amount equivalent to 0.003 mmol of gold) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 1 hour to allow the reaction. After the reaction, the solid catalyst was removed from the reaction solution by centrifugation, and low-boiling components were distilled off under reduced pressure. The resulting residue was then purified by silica gel column chromatography. In this case, n-hexane and ethyl acetate were used as the developing solvent, and the n-hexane / ethyl acetate (v / v) mixing ratio was varied from 100 / 0 to 90 / 10. As a result of the above, compound (1)-1-1 was obtained (yield 59%, selectivity 69%). The structure of compound (1)-1-1 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.40-1.45 (m, 2H), 1.05-1.35 (m, 8H), 0.91 (d, J= 7.2 Hz, 3H), 0.90 (t, J = 7.2 Hz, 3H), 0.53-0.63 (m, 1H), -0.04 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 32.0, 31.7, 29.5, 28.6, 22.8, 19.5, 14.2, 14.0, -3.2.

[0464] [ka]

[0465] [Example 2] Compound (1)-1-1 was obtained (yield 65%, selectivity 65%) in the same manner as in Example 1, except that compound (Au / TiO) (amount so that the amount of gold was 0.003 mmol) was used instead of the above compound (Au / ZrO) (amount so that the amount of gold was 0.003 mmol).

[0466] [Example 3] Compound (1)-1-1 was obtained (yield 58%, selectivity 62%) in the same manner as in Example 1, except that compound (Au / C) (amount so that the amount of gold was 0.003 mmol) was used instead of the above compound (Au / ZrO2) (amount so that the amount of gold was 0.003 mmol).

[0467] [Example 4] Compound (1)-1-1 was obtained (yield 49%, selectivity 49%) in the same manner as in Example 1, except that compound (Au / Fe2O3) (amount so that the amount of gold was 0.003 mmol) was used instead of the above compound (Au / ZrO2) (amount so that the amount of gold was 0.003 mmol).

[0468] [Example 5] Compound (1)-1-1 was obtained (yield 39%, selectivity 52%) in the same manner as in Example 1, except that compound (Au / ZrP2O7) (amount so that the amount of gold was 0.003 mmol) was used instead of the above compound (Au / ZrO2) (amount so that the amount of gold was 0.003 mmol).

[0469] [Example 6] Compound (1)-1-1 was obtained (yield 24%, selectivity 66%) in the same manner as in Example 1, except that compound (Au / AlO) (amount such that the amount of gold was 0.003 mmol) was used instead of the above compound (Au / ZrO).

[0470] In Examples 2 to 6, compound (1)-1-1 was analyzed by NMR, and the same data as in Example 1 was obtained. Therefore, the description of NMR data is omitted in these Examples.

[0471] As is clear from Examples 1 to 6, the target compound (1) was successfully obtained even when the type of catalyst was changed.

[0472] <<Production of Compound (1) (Consideration of Solvent Types)>> [Example 7] Under an argon gas atmosphere, compound (10)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / TiO2) obtained above (amount to make the amount of gold 0.003 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 1 hour to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-1 (yield 65%, selectivity 65%).

[0473] [ka]

[0474] [Example 8] Compound (1)-1-1 was obtained (yield 54%, selectivity 54%) in the same manner as in Example 7, except that 1,4-dioxane (1.0 mL) was used instead of toluene (1.0 mL) under an argon gas atmosphere.

[0475] [Example 9] Compound (1)-1-1 was obtained (yield 46%, selectivity 63%) in the same manner as in Example 7, except that benzotrifluoride (1.0 mL) was used instead of toluene (1.0 mL) under an argon gas atmosphere.

[0476] In Examples 7 to 9, compound (1)-1-1 was analyzed by NMR, and the same data as in Example 1 was obtained. Therefore, the description of NMR data is omitted in these Examples.

[0477] As is clear from Examples 7 to 9, the target compound (1) was successfully obtained even when the type of solvent was changed.

[0478] <<Production of Compound (1) (Reaction Temperature Consideration)>> [Example 10] Under an argon gas atmosphere, compound (10)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.003 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 1 hour to allow the reaction to occur. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-1 (yield 59%, selectivity 69%).

[0479] [ka]

[0480] [Example 11] Compound (1)-1-1 was obtained in the same manner as in Example 10 (yield 17%, selectivity 42%), except that the stirring temperature of the mixed solution (in other words, the reaction temperature) was changed from 100°C to 60°C.

[0481] [Example 12] Compound (1)-1-1 was obtained in the same manner as in Example 10 (yield 51%, selectivity 59%), except that the stirring temperature of the mixed solution (in other words, the reaction temperature) was changed from 100°C to 110°C.

[0482] [Example 13] Compound (1)-1-1 was obtained in the same manner as in Example 10 (yield 57%, selectivity 66%), except that the stirring temperature of the mixture (in other words, the reaction temperature) was changed from 100°C to 120°C.

[0483] [Example 14] Compound (1)-1-1 was obtained in the same manner as in Example 10 (yield 71%, selectivity 71%), except that the stirring time of the mixture (in other words, the reaction time) was changed from 1 hour to 4 hours.

[0484] In Examples 10 to 14, compound (1)-1-1 was analyzed by NMR, and the same data as in Example 1 was obtained. Therefore, the description of NMR data is omitted in these Examples.

[0485] As is clear from Examples 10 to 13, when the reaction temperature was 100° C. or higher, the target compound (1) was obtained in good yield. As is clear from Examples 10 and 14, the yield of compound (1) was improved by extending the reaction time.

[0486] <<Preparation of Compound (1) (Study on the Type of Leaving Group of Compound (10))>> [Example 15] Under an argon gas atmosphere, compound (10)-1-2 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount to make the amount of gold 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 1 hour to allow the reaction to occur. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-2 (yield 86%). The structure of compound (1)-1-2 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 1.24-1.37 (m, 16H), 0.89 (t, J = 6.8 Hz, 3H), 0.48 (t, J = 8.0 Hz, 2H), -0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 33.7, 31.9, 29.7, 29.6, 29.4, 29.3, 23.9, 22.7, 16.7, 14.1, -1.6.

[0487] [ka]

[0488] [Example 16] Compound (1)-1-2 was obtained (yield 99%) in the same manner as in Example 15, except that compound (10)-1-3 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0489] [ka]

[0490] [Example 17] Compound (1)-1-2 was obtained (yield 21%) in the same manner as in Example 15, except that compound (10)-1-4 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0491] [ka]

[0492] [Example 18] Compound (1)-1-2 was obtained in the same manner as in Example 17, except that the stirring time of the mixture (in other words, the reaction time) was changed from 1 hour to 17 hours (yield: 39%).

[0493] [Example 19] Compound (1)-1-2 was obtained (yield 25%) in the same manner as in Example 15, except that compound (10)-1-5 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0494] [ka]

[0495] [Example 20] Compound (1)-1-2 was obtained (yield 68%) in the same manner as in Example 19, except that the stirring time of the mixture (in other words, the reaction time) was changed from 1 hour to 17 hours.

[0496] [Example 21] Compound (1)-1-2 was obtained (yield 97%) in the same manner as in Example 15, except that compound (10)-1-6 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0497] [ka]

[0498] [Example 22] Compound (1)-1-2 was obtained (yield 99%) in the same manner as in Example 15, except that compound (10)-1-7 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0499] [ka]

[0500] [Example 23] Compound (1)-1-2 was obtained (yield 99%) in the same manner as in Example 15, except that compound (10)-1-8 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 1 hour to 17 hours.

[0501] [ka]

[0502] [Example 24] Compound (1)-1-2 was obtained (yield 99%) in the same manner as in Example 15, except that compound (10)-1-9 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol).

[0503] [ka]

[0504] In Examples 16 to 24, compound (1)-1-2 was analyzed by NMR, and the same data as in Example 15 was obtained. Therefore, the description of NMR data is omitted in these Examples.

[0505] The compound (10) in Examples 15 to 20 is a carboxylic acid ester, the compound (10) in Example 21 is a carbonate ester, the compound (10) in Example 22 is a urethane, the compound (10) in Example 23 is an ether, and the compound (10) in Example 24 is a brominated alkane. These are compounds of different categories, and the leaving group (X in general formula (1) 11 However, in both cases, the target compound (1) was obtained in good yield.

[0506] <<Production of Compound (1) (Investigation of the Main Structure of Compound (1))>> [Example 25] Under an argon gas atmosphere, compound (10)-1-2 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 3 hours to allow the reaction to occur. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-2 (yield 92%).

[0507] [ka]

[0508] [Example 26] Compound (1)-1-2 was obtained (yield 93%) in the same manner as in Example 25, except that the reaction was carried out under an air atmosphere instead of an argon gas atmosphere.

[0509] In Examples 25 and 26, compound (1)-1-2 was analyzed by NMR, and the same data as in Example 15 was obtained. Therefore, the description of NMR data is omitted in these Examples.

[0510] [Example 27] Compound (1)-1-3 was obtained (yield 95%) in the same manner as in Example 25, except that compound (10)-1-10 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 4 hours. The structure of compound (1)-1-3 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 3.54 (t, J = 6.7 Hz, 2H), 1.74-1.81 (m, 2H), 1.41-1.45 (m, 2H), 1.30 (m, 8H), 0.46-0.50 (m, 2H), -0.02 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 45.2, 33.5, 32.7, 29.2, 28.8, 26.9, 23.9, 16.7, -1.6.

[0511] [ka]

[0512] [Example 28] Compound (1)-1-4 was obtained (yield 96%) in the same manner as in Example 25, except that compound (10)-1-11 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol). The structure of compound (1)-1-4 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.76-5.86 (m, 1H), 4.91-5.02 (m, 2H), 2.02-2.08 (m, 2H), 1.37-1.44 (m, 2H), 1.26-1.35 (m, 2H), 0.47-0.51 (m, 2H), -0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 139.2, 114.1, 33.6, 32.8, 23.4, 16.5, -1.6.

[0513] [ka]

[0514] [Example 29] Compound (1)-1-5 was obtained (yield 72%) in the same manner as in Example 25, except that compound (10)-1-12 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 20 hours. The structure of compound (1)-1-5 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.19-7.34 (m, 5H), 2.66-2.71 (m, 2H), 0.91-0.95 (m, 2H), 0.07 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 145.3, 128.8, 127.7, 125.4, 30.0, 18.7, -1.7.

[0515] [ka]

[0516] [Example 30] Compound (1)-1-6 was obtained (yield 83%) in the same manner as in Example 25, except that compound (10)-1-13 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 4 hours. The structure of compound (1)-1-6 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.77-5.87 (m, 1H), 4.97-5.02 (m, 1H), 4.92-4.95 (m, 1H), 2.02-2.08 (m, 2H), 1.37-1.40 (m, 2H), 1.28 (m, 12H), 0.46-0.50 (m, 2H), 0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 139.2, 114.1, 33.9, 33.7, 29.6, 29.4, 29.2, 29.0, 23.9, 16.7, 1.6.

[0517] [ka]

[0518] [Example 31] Compound (1)-1-7 was obtained (yield 56%) in the same manner as in Example 25, except that compound (10)-1-14 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol). The structure of compound (1)-1-7 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.35-5.42 (m, 1H), 5.25-5.31 (m, 1H), 1.99-2.07 (m, 4H), 1.25-1.39 (m, 6H), 0.90 (t, J = 6.9 Hz, 3H), 0.55-0.59 (m, 2H), 0.00 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 132.8, 128.4, 31.5, 29.4, 27.0, 22.6, 21.5, 17.1, 14.1, -1.6.

[0519] [ka]

[0520] [Example 32] Compound (1)-1-8 was obtained (yield 44%) in the same manner as in Example 25, except that compound (10)-1-15 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 6 hours. The structure of compound (1)-1-8 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 2.11-2.22 (m, 4H), 1.26-1.49 (m, 8H), 0.89 (t, J = 6.7 Hz, 3H), 0.77 (t, J = 7.8 Hz, 2H), 0.02 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 82.2, 79.6, 31.4, 29.1, 28.6, 22.6, 18.8, 16.5, 14.1, 13.3, -1.6.

[0521] [ka]

[0522] [Example 33] Compound (1)-1-9 was obtained (yield 84%) in the same manner as in Example 25, except that compound (10)-1-16 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 2 hours. The structure of compound (1)-1-9 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.09-5.13 (m, 1H), 1.88-2.05 (m, 1H), 1.69 (s, 3H), 1.61 (s, 3H), 1.24-1.39 (m, 3H), 1.07-1.17 (m, 2H), 0.86 (d, J = 6.4 Hz, 3H), 0.36-0.53 (m, 2H), -0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 130.6, 124.8, 36.2, 34.8, 30.4, 25.4, 25.3, 18.9, 17.3, 13.0, -2.0.

[0523] [ka]

[0524] [Example 34] Compound (1)-1-10 was obtained (yield 96%) in the same manner as in Example 25, except that compound (10)-1-17 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 2 hours. The structure of compound (1)-1-10 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.65-7.67 (m, 1H), 7.36-7.38 (m, 1H), 7.21-7.25 (m, 1H), 7.10-7.14 (m, 2H), 6.50-6.51 (m, 1H), 4.13 (t, J = 7.1 Hz, 2H), 1.82-1.89 (m, 2H), 1.30-1.34 (m, 10H), 0.47-0.51 (m, 2H), 0.00 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 135.9, 128.5, 127.8, 121.2, 120.9, 119.1, 109.3, 100.7, 46.4, 33.5, 30.2, 29.2, 29.2, 27.1, 23.9, 16.6, -1.6.

[0525] [ka]

[0526] [Example 35] Compound (1)-1-1 was obtained in the same manner as in Example 25 (yield 71%), except that compound (10)-1-1 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 4 hours. In this example, compound (1)-1-1 was analyzed by NMR, and the same data as in Example 1 was obtained. Therefore, in this example, the description of the NMR data is omitted.

[0527] [ka]

[0528] [Example 36] Compound (1)-1-11 was obtained in the same manner as in Example 25 (yield 38%), except that compound (10)-1-18 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 4 hours. The structure of compound (1)-1-10 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.21-1.43 (m, 16H), 0.90 (t, J = 6.9 Hz, 3H), 0.89 (t, J = 6.5 Hz, 3H), 0.49-0.55 (m, 1H), 0.03 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 31.9, 31.4, 29.8, 29.8, 29.4, 29.1, 25.5, 23.2, 22.8, 14.1, 2.1.

[0529] [ka]

[0530] [Example 37] Compound (1)-1-12 was obtained (yield 38%) in the same manner as in Example 25, except that compound (10)-1-19 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 4 hours. The structure of compound (1)-1-12 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.24-7.24 (m, 2H), 7.13-7.15 (m, 2H), 2.79-3.06 (m, 4H), 1.57-1.67 (m, 1H), 0.06 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 177.9, 125.8, 124.1, 34.7, 26.0, -3.0.

[0531] [ka]

[0532] [Example 38] Compound (1)-1-13 was obtained (yield 77%) in the same manner as in Example 25, except that compound (10)-1-20 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 2 hours. The structure of compound (1)-1-13 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.29-7.32 (m, 2H), 7.18-7.22 (m, 3H), 2.80-2.86 (m, 1H), 2.49-2.57 (m, 1H), 1.77-1.85 (m, 1H), 1.39-1.48 (m, 1H), 1.03 (d, J = 7.3 Hz, 3H), 0.63-0.72 (m, 1H), 0.01 (s, 3H); 13 C NMR (100 MHz, CDCl3, ppm) δ 143.1, 128.4, 128.2, 125.5, 35.0, 33.9, 19.4, 13.8, -3.3.

[0533] [ka]

[0534] [Example 39] Compound (1)-1-14 was obtained (yield 84%) in the same manner as in Example 25, except that compound (10)-1-1 (0.3 mmol) was used instead of compound (10)-1-2 (0.3 mmol), compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol), and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 1 hour. The structure of compound (1)-1-14 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.26-1.52 (m, 10H), 1.24 (s, 9H), 0.90 (d, J = 7.4 Hz, 3H), 0.90 (t, J = 7.4 Hz, 3H), 0.07 (s, 3H); 13 C NMR (100 MHz, CDCl3, ppm) δ 71.8, 32.1, 32.0, 31.2, 29.5, 28.9, 22.8, 21.3, 14.2, 13.6, 0.7, 0.9.

[0535] [ka]

[0536] [Example 40] Under an argon gas atmosphere, compound (10)-1-21 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.003 mmol) was suspended as a catalyst. The resulting mixture was stirred at 80 °C for 2 hours to allow the reaction to occur. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-15 (yield 82%). The structure of compound (1)-1-15 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.27-7.34 (m, 5H), 7.15-7.20 (m, 1H), 6.26-6.28 (m, 2H), 1.69-1.70 (m, 2H), 0.08 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 138.5, 128.4, 128.2, 127.8, 126.1, 125.5, 23.9, -1.8.

[0537] [ka]

[0538] [Example 41] Compound (1)-1-16 was obtained (yield 42%) in the same manner as in Example 40, except that compound (10)-1-22 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 3 hours. The obtained compound (1)-1-16 was a mixture containing 70 mol% of E-isomer and 30 mol% of Z-isomer relative to the total amount of the compound. The structure of compound (1)-1-16 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.33-5.43 (m, 1H), 5.20-5.30 (m, 1H), 1.93-1.99 (m, 2H), 1.33-1.48 (m, 4H), 0.87-0.93 (m, 3H), -0.01 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 128.8, 126.1, 34.9, 23.1, 22.6, 13.6, -2.0.

[0539] [ka]

[0540] [Example 42] Compound (1)-1-17 was obtained (yield 45%) in the same manner as in Example 40, except that compound (10)-1-23 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 3 hours. The obtained compound (1)-1-17 was a mixture containing 69 mol% of E-isomer and 31 mol% of Z-isomer relative to the total amount. The structure of compound (1)-1-17 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.09-5.19 (m, 2H), 2.00-209 (m, 4H), 1.70 (s, 3H), 1.68 (s, 3H), 1.70 (s, 3H), 1.55 (s, 3H), 1.40 (d, J = 8.2 Hz, 2H), -0.01 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 132.2, 131.1, 124.5, 120.3, 40.0, 26.8, 25.8, 18.6, 17.7, 15.7, -1.7.

[0541] [ka]

[0542] [Example 43] Compound (1)-1-18 was obtained (yield 59%) in the same manner as in Example 40, except that compound (10)-1-24 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 3 hours. The structure of compound (1)-1-18 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 4.08 (s, 5H), 3.98 (d, J = 8.6 Hz, 4H), 1.73 (s, 2H), 0.06 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 87.4, 68.8, 68.0, 66.6, 19.6, -1.8.

[0543] [ka]

[0544] [Example 44] Compound (1)-1-19 was obtained (yield 90%) in the same manner as in Example 40, except that compound (10)-1-25 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol), compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol), and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 1 hour. The structure of compound (1)-1-19 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.19-7.23 (m, 2H), 7.06-7.09 (m, 3H), 2.16 (s, 2H), 1.25 (s, 9H), 0.10 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 139.8, 128.4, 128.0, 123.9, 72.4, 32.0, 28.8, 0.6.

[0545] [ka]

[0546] [Example 45] Compound (1)-1-20 was obtained (yield 83%) in the same manner as in Example 40, except that compound (10)-1-26 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol), compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol), and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 4 hours. The structure of compound (1)-1-20 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.02-7.03 (m, 2H), 6.95-6.97 (m, 2H), 2.30 (s, 3H), 2.11 (s, 2H), 1.26 (s, 9H), 0.09 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 136.5, 133.1, 128.7, 128.3, 72.3, 32.0, 28.2, 20.9, 0.5.

[0547] [ka]

[0548] [Example 46] Compound (1)-1-21 was obtained (yield 89%) in the same manner as in Example 40, except that compound (10)-1-27 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol), compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol), and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 4 hours. The structure of compound (1)-1-21 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.45 (d, J = 8.1 Hz, 2H), 7.15 (d, J = 8.0 Hz, 2H), 2.20 (s, 2H), 1.23 (s, 9H), 0.10 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 144.5, 128.4, 124.8, 124.8, 72.6, 32.0, 29.2, 0.6.

[0549] [ka]

[0550] [Example 47] Compound (1)-1-22 was obtained (yield 83%) in the same manner as in Example 40, except that compound (10)-1-28 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 0.5 hours. The structure of compound (1)-1-22 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 6.92-7.00 (m, 4H), 2.28 (s, 3H), 2.07 (s, 2H), 0.00 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 169.7, 147.3, 138.0, 128.6, 121.0, 26.4, 21.1, -2.0.

[0551] [ka]

[0552] [Example 48] Compound (1)-1-23 was obtained (yield 87%) in the same manner as in Example 40, except that compound (10)-1-29 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol), compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol), and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 4 hours. The structure of compound (1)-1-23 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 6.98-7.03 (m, 2H), 6.87-6.93 (m, 2H), 2.09 (s, 2H), 1.24 (s, 9H), 0.09 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 160.2 (d, J = 240.8 Hz), 135.3 (d, J = 2.9 Hz), 129.4 (d, J = 7.3 Hz), 114.6 (d, J = 21.0 Hz), 72.4, 32.0, 27.7, 0.5.

[0553] [ka]

[0554] [Example 49] Compound (1)-1-24 was obtained (yield 87%) in the same manner as in Example 40, except that compound (10)-1-30 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol). The structure of compound (1)-1-24 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.15-7.19 (m, 2H), 6.97-7.00 (m, 2H), 2.10 (s, 2H), 1.23 (s, 9H), 0.09 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 138.4, 129.6, 129.5, 128.0, 42.5, 32.0, 28.2, 0.6.

[0555] [ka]

[0556] [Example 50] Compound (1)-1-25 was obtained (yield 77%) in the same manner as in Example 40, except that compound (10)-1-31 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2. The structure of compound (1)-1-25 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.10-7.14 (m, 1H), 7.03-7.07 (m, 2H), 6.92-6.94 (m, 1H), 2.10 (s, 2H), 1.24 (s, 9H), 0.10 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 142.1, 133.6, 129.1,128.4, 126.6, 124.0, 72.5, 32.0, 28.6, 0.6.

[0557] [ka]

[0558] [Example 51] Compound (1)-1-26 was obtained (yield 93%) in the same manner as in Example 40, except that compound (10)-1-32 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol). The structure of compound (1)-1-26 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 6.92-7.00 (m, 4H), 2.28 (s, 3H), 2.07 (s, 2H), 0.00 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 169.7, 147.3, 138.0, 128.6, 121.0, 26.4, 21.1, -2.0.

[0559] [ka]

[0560] [Example 52] Compound (1)-1-27 was obtained (yield 53%) in the same manner as in Example 40, except that compound (10)-1-33 (0.3 mmol) was used instead of compound (10)-1-21 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 3 hours. The structure of compound (1)-1-27 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.11-7.26 (m, 5H), 2.18 (q, J = 7.6 Hz, 1H), 1.39 (d, J = 7.4 Hz, 3H), 1.22 (s, 9H), 0.05 (d, J = 4.1 Hz, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 145.5, 127.7, 127.5, 124.1, 72.2, 31.9, 31.3, 14.5, -0.8.

[0561] [ka]

[0562] [Example 53] Under an argon gas atmosphere, compound (10)-2-1 (0.3 mmol) and compound (9)-1-1 (1.8 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) (0.018 mmol) obtained above was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 18 hours to allow the reaction to proceed. Thereafter, the same method as in Example 1 was used to obtain compound (1)-2-1 (yield 91%). The structure of compound (1)-2-1 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.29-1.33 (m, 4H), 0.47-0.51 (m, 4H), -0.02 (s, 18H); 13 C NMR (100 MHz, CDCl3, ppm) δ 27.9, 16.5, -1.6.

[0563] [ka]

[0564] [Example 54] Compound (1)-2-2 was obtained (yield 99%) in the same manner as in Example 53, except that compound (10)-2-2 (0.3 mmol) was used instead of compound (10)-2-1 (0.3 mmol). The structure of compound (1)-2-2 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.26-1.30 (m, 8H), 0.46-0.50 (m, 4H), -0.02 (s, 18H); 13 C NMR (100 MHz, CDCl3, ppm) δ 33.4, 23.9, 16.7, -1.6.

[0565] [ka]

[0566] [Example 55] Compound (1)-2-3 was obtained (yield 99%) in the same manner as in Example 53, except that compound (10)-2-3 (0.3 mmol) was used instead of compound (10)-2-1 (0.3 mmol). The structure of compound (1)-2-3 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.27-1.29 (m, 16H), 0.46-0.50 (m, 4H), -0.02 (s, 18H); 13 C NMR (100 MHz, CDCl3, ppm) δ 33.7, 29.7, 29.4, 23.9, 16.7, -1.6.

[0567] [ka]

[0568] [Example 56] Compound (1)-2-4 was obtained (yield 79%) in the same manner as in Example 53, except that compound (10)-2-4 (0.3 mmol) was used instead of compound (10)-2-1 (0.3 mmol). The structure of compound (1)-2-4 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ6.86 (s, 4H), 2.02 (s, 4H), -0.01(s, 18H); 13 C NMR(100 MHz, CDCl3, ppm) δ135.5, 127.8, 26.2, -1.9.

[0569] [ka]

[0570] [Example 57] Compound (1)-2-5 was obtained (yield 69%) in the same manner as in Example 53, except that compound (10)-2-5 (0.3 mmol) was used instead of compound (10)-2-1 (0.3 mmol). The structure of compound (1)-2-5 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ6.97-6.91 (m, 4H), 2.04 (s, 4H), 0.02 (s, 4H); 13 C NMR(100 MHz, CDCl3, ppm) δ136.9, 128.9, 123.8, 24.1, -1.3

[0571] [ka]

[0572] <<Production of Compound (1) (Consideration of the Type of Compound (9))>> [Example 58] Under an argon gas atmosphere, compound (10)-1-2 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 2 hours to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-2 (yield 92%). In this example, compound (1)-1-2 was analyzed by NMR, and the same data as in Example 15 was obtained. Therefore, in this example, the description of the NMR data is omitted.

[0573] [ka]

[0574] [Example 59] Compound (1)-1-28 was obtained (yield 63%) in the same manner as in Example 58, except that compound (9)-1-3 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 15 hours. The structure of compound (1)-1-28 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ7.24-7.20 (m, 2H), 7.09-7.00 (m, 3H), 2.10 (s, 2H), 1.29 (s, 16H), 0.91 (t, J=7.2Hz, 3H), 0.52 (t, J=7.6Hz, 2H), -0.02 (s, 6H): 13 C NMR(100 MHz, CDCl3, ppm) δ140.5, 128.1, 128.0, 123.8, 33.6, 31.9, 29.7, 29.6, 29.4, 25.6, 23.8, 22.7, 14.8, 14.1, -3.6

[0575] [ka]

[0576] [Example 60] Compound (1)-1-29 was obtained (yield 54%) in the same manner as in Example 58, except that compound (9)-1-4 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol). The structure of compound (1)-1-29 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.27-1.31 (m, 16H), 0.89 (t, J = 6.8 Hz, 3H), 0.55 (t, J = 7.6 Hz, 2H), 0.10 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 71.9, 33.6, 32.1, 32.0, 29.7, 29.7, 29.4, 29.4, 23.5, 22.7, 18.8, 14.1, 1.0.

[0577] [ka]

[0578] [Example 61] Compound (1)-1-30 was obtained (yield 72%) in the same manner as in Example 58, except that compound (9)-1-5 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol). The structure of compound (1)-1-30 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.27-1.33 (m, 16H), 0.89 (t, J = 7.0 Hz, 3H), 0.49-0.53 (m, 2H), 0.07 (s, 9H), 0.04 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 33.5, 31.9, 29.7, 29.6, 26.4, 26.4, 23.3, 22.7, 18.4, 14.1, 2.0, 0.4.

[0579] [ka]

[0580] [Example 62] Compound (1)-1-31 was obtained (yield 43%) in the same manner as in Example 58, except that compound (9)-1-6 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol), the stirring temperature of the mixture (i.e., the reaction temperature) was changed from 100°C to 130°C, and the stirring time of the mixture (i.e., the reaction time) was changed from 2 hours to 15 hours. The structure of compound (1)-1-31 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ7.55-7.52 (m, 2H), 7.38-7.36 (m, 3H), 1.32-1.28 (m, 16H), 0.92 (t, 7.2Hz, 3H), 0.77 (t, 8.4Hz, 2H), 0.29 (s, 6H); 13 C NMR(100 MHz, CDCl3, ppm) δ139.7, 133.5, 128.7, 127.7, 33.6, 31.9, 29.7, 29.6, 29.4, 29.3, 23.9, 22.7, 15.7, 14.2, -3.0.

[0581] [ka]

[0582] [Example 63] Compound (1)-1-32 was obtained (yield 42%) in the same manner as in Example 58, except that compound (9)-1-7 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol), the stirring temperature of the mixture (i.e., the reaction temperature) was changed from 100°C to 130°C, and the stirring time of the mixture (i.e., the reaction time) was changed from 2 hours to 15 hours. The structure of compound (1)-1-32 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ7.43 (d, J=7.6 Hz, 2H), 7.20 (d, J=8.0Hz, 2H), 2.37 (s, 3H), 1.32-1.27 (m, 16H), 0.91 (t, J=6.8Hz, 3H), 0.75 (t, J=8Hz, 2H), 0.26 (s, 6H): 13C NMR(100 MHz, CDCl3, ppm) δ138.5, 136.1, 133.6, 128.5, 33.7, 31.9, 29.7, 29.6, 29.4, 29.3, 23.9, 22.7, 21.5, 15.8, 14.2.

[0583] [ka]

[0584] [Example 64] Compound (1)-1-33 was obtained (yield 63%) in the same manner as in Example 58, except that compound (9)-1-8 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol), the stirring temperature of the mixture (i.e., the reaction temperature) was changed from 100°C to 130°C, and the stirring time of the mixture (i.e., the reaction time) was changed from 2 hours to 24 hours. The structure of compound (1)-1-33 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ7.55-7.52 (m, 4H), 7.39-7.35 (m, 6H), 1.26 (s, 18H), 1.09 (t, J=8.8Hz, 2H), 0.91 (t, J=6.8Hz, 3H), 0.57 (s, 3H); 13 C NMR(100 MHz, CDCl3, ppm) δ137.5, 134.4, 129.0, 127.7, 33.7, 31.9, 29.6, 29.3, 29.2, 23.8, 22.7, 14.1, -4.4.

[0585] [ka]

[0586] [Example 65] Under an argon gas atmosphere, compound (10)-1-34 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount of gold: 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 18 hours to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (1)-1-34 (yield 98%). The structure of compound (1)-1-34 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3) δ 1.18-1.44 (m, 12H), 0.86-1.02 (m, 3H), 0.47-0.59 (m, 2H), 0.03 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ = 34.1, 32.4, 29.8, 29.8, 24.4, 23.1, 17.0, 14.4, -1.5.

[0587] [ka]

[0588] <<Production of Compound (2)>> [Example 66] Under an argon gas atmosphere, compound (20)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 2 hours to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (2)-1-1 (yield 82%). The structure of compound (2)-1-1 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 3.76-3.82 (m, 1H), 3.42 (d, J = 5.8 Hz, 2H), 1.26-1.65 (m, 6H), 0.50 (t, J = 8.2 Hz, 2H), 0.15 (s, 9H), -0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 72.6, 49.0, 64.7, 29.3, 23.9, 16.7, 0.3, -1.7.

[0589] [ka]

[0590] [Example 67] Compound (2)-1-2 was obtained (yield 41%) in the same manner as in Example 66, except that compound (20)-1-2 (0.3 mmol) was used instead of compound (20)-1-1 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 4 hours. The structure of compound (2)-1-2 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 3.76-3.83 (m, 1H), 3.52-3.56 (m, 1H), 3.36-3.40 (m, 1H), 1.31-1.61 (m, 4H), 0.44-0.58 (m, 2H), -0.01 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 71.1, 41.1, 39.2, 20.5, 16.9, -1.4.

[0591] [ka]

[0592] [Example 68] Compound (2)-1-3 was obtained (yield 95%) in the same manner as in Example 66, except that compound (20)-1-3 (0.3 mmol) was used instead of compound (20)-1-1 (0.3 mmol). The structure of compound (2)-1-3 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 3.99-4.03 (m, 1H), 3.88-3.93 (m, 1H), 3.80-3.86 (m, 1H), 2.07 (s, 3H), 1.37-1.49 (m, 3H), 1.22-1.32 (m, 1H), 0.41-0.55 (m, 2H), 0.13 (s, 9H), 0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 170.9, 70.0, 68.7, 38.1, 21.0, 19.9, 16.6, 0.3, -1.7.

[0593] [ka]

[0594] [Example 69] Compound (2)-1-4 was obtained (yield 11%) in the same manner as in Example 66, except that compound (20)-1-4 (0.3 mmol) was used instead of compound (20)-1-1 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 4 hours. The structure of compound (2)-1-4 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 3.93 (quin, J = 6.3 Hz, 1H), 2.43-2.46 (m, 2H), 1.55-1.62 (m, 2H), 1.20-1.45 (m, 2H), 0.46-0.52 (m, 2H), 0.17 (s, 9H), -0.01 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 68.2, 41.0, 26.4, 19.9, 16.5, 0.2, -1.7.

[0595] [ka]

[0596] [Example 70] Compound (2)-2-1 was obtained (yield 79%) in the same manner as in Example 66, except that compound (20)-2-1 (0.3 mmol) was used instead of compound (20)-1-1 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 2 hours to 15 hours. The structure of compound (2)-2-1 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.16-7.18 (m, 1H), 7.03-7.08 (m, 1H), 6.88-6.92 (m, 1H), 6.76-6.78 (m, 1H), 2.55-2.59 (m, 2H), 0.80-0.85 (m, 2H), 0.29 (s, 9H), 0.04 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 152.9, 136.0, 129.2, 126.3, 121.3, 118.7, 24.7, 17.3, 0.5, -1.7.

[0597] [ka]

[0598] [Example 71] Compound (2)-1-6 was obtained (yield 83%) in the same manner as in Example 66, except that compound (20)-1-5 (0.3 mmol) was used instead of compound (20)-1-1 (0.3 mmol). The structure of compound (2)-1-6 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 3.76-3.82 (m, 1H), 3.42 (d, J = 5.8 Hz, 2H), 1.26-1.65 (m, 6H), 0.50 (t, J = 8.2 Hz, 2H), 0.15 (s, 9H), -0.02 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 72.6, 49.0, 64.7, 29.3, 23.9, 16.7, 0.3, -1.7.

[0599] [ka]

[0600] [Example 72] Under an argon gas atmosphere, compound (20)-2-2 (0.3 mmol) and compound (9)-1-2 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 8 hours to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (2)-2-2 (yield 80%). The structure of compound (2)-2-2 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 6.22-6.25 (m, 1H), 4.47-4.52 (m, 1H), 2.08-2.14 (m, 2H), 1.33-1.41 (m, 2H), 1.30 (s, 9H), 1.24 (s, 9H), 0.57-0.61 (m, 2H), 0.18 (s, 6H), 0.09 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 137.2, 110.9, 73.0, 71.9, 32.1, 31.8, 27.5, 23.7, 18.7, 0.9, -0.5.

[0601] [ka]

[0602] [Example 73] Compound (2)-2-3 was obtained in the same manner as in Example 72, except that compound (9)-1-1 (0.9 mmol) was used instead of compound (9)-1-2 (0.9 mmol). In this example, the structure of compound (2)-2-3 was confirmed by gas chromatography-mass spectrometry (GC-MS), and the data are shown below. MS (EI) m / z (%) 230 (2, [M] + ), 147 (10), 129 (31), 73 (100).

[0603] [ka]

[0604] <<Production of Compound (3) (Decomposition of Polyester)>> [Example 74] Under an argon gas atmosphere, compound (30)-1-1 (poly(1,4-butylene succinate)) (0.06 g) and compound (9)-1-1 (0.3 g) were dissolved in toluene (1 mL), and the compound (Au / ZrO2) (0.058 g) obtained above was suspended as a catalyst. The resulting mixture was stirred at 130 °C for 4 hours to allow the reaction to proceed. Thereafter, compound (3)-1-1 was obtained (yield 99%) in the same manner as in Example 1. Compound (3)-1-1 was the same as compound (1)-2-1 obtained in Example 53, and when analyzed by NMR, data similar to that in Example 53 was obtained. Therefore, in this example, description of NMR data is omitted.

[0605] [ka]

[0606] [Example 75] Compound (3)-1-1 was obtained (yield 87%) in the same manner as in Example 74, except that compound (30)-1-2 (poly(1,4-butylene adipate)) (0.052 g) was used instead of compound (30)-1-1 (0.06 g), the stirring temperature of the mixture (i.e., the reaction temperature) was changed from 130°C to 100°C, and the stirring time of the mixture (i.e., the reaction time) was changed from 4 hours to 6 hours. In this example, compound (3)-1-1 was analyzed by NMR, and the same data as in Example 74 (Example 53) was obtained. Therefore, in this example, the description of NMR data is omitted.

[0607] [ka]

[0608] [Example 76] Compound (3)-1-2 was obtained (yield 94%) in the same manner as in Example 74, except that compound (30)-1-3 (polycarbonate) (0.043 g) was used instead of compound (30)-1-1 (0.06 g), the stirring temperature (i.e., reaction temperature) of the mixture was changed from 130°C to 100°C, and the stirring time (i.e., reaction time) of the mixture was changed from 4 hours to 6 hours. Compound (3)-1-2 was the same as compound (1)-2-2 obtained in Example 54, and when analyzed by NMR, data similar to that in Example 54 was obtained. Therefore, NMR data is not shown in this example.

[0609] [ka]

[0610] As is clear from Examples 74 to 76, compound (3) was obtained in high yield under mild conditions even when a polymer was used as compound (30). From the yield of compound (3), it was estimated that the target reaction was able to take place at the majority of reactive sites in compound (30), and that almost all of compound (30) was decomposed.

[0611] <<Production of Compound (4)>> [Example 77] Under an argon gas atmosphere, compound (40)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 1 hour to allow the reaction to occur. Thereafter, the same method as in Example 1 was used to obtain compound (4)-1-1 (yield 90%). The structure of compound (4)-1-1 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 2.05-2.08 (m, 4H), 1.92 (t, J = 7.0 Hz, 2H), 1.28-1.64 (m, 10H), 0.90 (t, J = 7.1 Hz, 3H), 0.06 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 201.0, 96.9, 94.6, 31.5, 31.3, 29.3, 27.8, 26.4, 22.3, 14.1, -1.2.

[0612] [ka]

[0613] [Example 78] Compound (4)-1-2 was obtained (yield 72%) in the same manner as in Example 77, except that compound (9)-1-2 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol). The structure of compound (4)-1-2 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 2.08 (t, J = 5.8 Hz, 4H), 1.98 (t, J = 7.2 Hz, 2H), 1.30-1.58 (m, 10H), 1.26 (s, 9H), 0.90 (t, J = 7.2 Hz, 3H), 0.17 (s, 6H); 13 C NMR (100 MHz, CDCl3, ppm) δ 202.0, 97.2, 96.0, 72.4, 31.9, 31.3, 30.9, 28.9, 27.6, 26.4, 22.4, 14.1, 1.0.

[0614] [ka]

[0615] [Example 79] Compound (4)-1-3 was obtained (yield 60%) in the same manner as in Example 77, except that compound (9)-1-8 (0.9 mmol) was used instead of compound (9)-1-1 (0.9 mmol). The structure of compound (4)-1-3 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.54-7.56 (m, 4H), 7.34-7.38 (m, 6H), 1.95-2.10 (m, 6H), 1.24-1.55 (m, 10H), 0.84 (t, J = 7.3 Hz, 3H), 0.63 (s, 3H); 13 C NMR (100 MHz, CDCl3, ppm) δ 204.0,136.8, 134.9, 129.0, 127.6, 97.7, 91.7, 31.2, 31.0, 29.8, 27.2, 26.2, 22.2, 14.0, -3.5.

[0616] [ka]

[0617] [Example 80] Compound (4)-1-4 was obtained (yield 89%) in the same manner as in Example 77, except that compound (40)-1-2 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-4 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.23-7.30 (m, 4H), 7.12-7.16 (m, 1H), 2.18-2.21 (m, 4H), 1.49-1.66 (m, 6H), 0.22 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 204.3, 138.9, 128.3, 127.6, 125.6, 98.5, 98.3, 30.8, 27.5, 26.3, 0.0.

[0618] [ka]

[0619] [Example 81] Compound (4)-1-5 was obtained (yield 69%) in the same manner as in Example 77, except that compound (40)-1-3 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-5 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 2.05-2.08 (m, 4H), 1.48-1.60 (m, 6H), 1.07 (s, 9H), 0.12 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 200.9, 105.6, 97.4, 35.0, 31.5, 31.3, 27.5, 26.4, 1.5.

[0620] [ka]

[0621] [Example 82] Compound (4)-1-6 was obtained (yield 64%) in the same manner as in Example 77, except that compound (40)-1-4 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-6 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 2.04-2.07 (m, 4H), 1.49-1.55 (m, 6H), 0.090 (s, 18H); 13 C NMR (100 MHz, CDCl3, ppm) δ 208.1, 87.7, 87.1, 30.2, 27.6, 26.5, 0.3.

[0622] [ka]

[0623] [Example 83] Compound (4)-1-7 was obtained (yield 80%) in the same manner as in Example 77, except that compound (40)-1-5 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-7 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.51-7.55 (m, 2H), 7.33-7.34 (m, 3H), 2.04-2.11 (m, 4H), 1.46-1.59 (m, 6H), 0.38 (s, 6H), -0.01 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 209.6, 139.8, 133.8, 128.6, 127.5, 87.6, 86.3, 30.0, 27.4, 26.4, 0.2, -1.2.

[0624] [ka]

[0625] [Example 84] Compound (4)-1-8 was obtained (yield 81%) in the same manner as in Example 77, except that compound (40)-1-6 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-8 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 1.89-1.93 (m, 2H), 1.64 (s, 6H), 1.29-1.41 (m, 4H), 0.90 (t, J = 7.2 Hz, 3H), 0.05 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 204.5, 94.7, 89.1, 31.6, 29.4, 22.4, 20.1, 14.1, -1.2.

[0626] [ka]

[0627] [Example 85] Compound (4)-1-9 was obtained (yield 73%) in the same manner as in Example 77, except that compound (40)-1-7 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-9 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 4.77-4.80 (m, 1H), 1.92-1.98 (m, 4H), 1.31-1.44 (m, 8H), 0.90 (t, J = 7.2 Hz, 6H), 0.08 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 205.4, 96.3, 85.5, 32.0, 31.4, 29.2, 28.3, 22.5, 22.3, 14.1, 14.0, -1.4.

[0628] [ka]

[0629] [Example 86] Compound (4)-1-10 was obtained (yield 58%) in the same manner as in Example 77, except that compound (40)-1-8 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-10 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 4.82-4.85 (m, 1H), 1.92-1.96 (m, 2H), 1.31-1.43 (m, 4H), 1.10-1.18 (m, 1H), 0.90 (t, J = 7.2 Hz, 3H), 0.60-0.64 (m, 2H), 0.26-0.29 (m, 2H), 0.08 (s, 9H); 13C NMR (100 MHz, CDCl3, ppm) δ 204.7, 98.8, 89.5, 31.4, 29.3, 22.5, 14.0, 8.8, 6.8, 6.4, -1.4.

[0630] [ka]

[0631] [Example 87] Compound (4)-1-11 was obtained (yield 93%) in the same manner as in Example 77, except that compound (40)-1-9 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-11 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.13-7.29 (m, 10H), 5.18 (t, J = 6.8 Hz, 6H), 2.74-2.80 (m, 2H), 2.37-2.44 (m, 2H), 0.21-0.23 (s, 9H) 13 C NMR (100 MHz, CDCl3, ppm) δ 208.1, 141.7, 137.7, 128.5, 128.3, 127.5, 125.9, 125.8, 100.5, 86.6, 35.9, 30.2, -0.3.

[0632] [ka]

[0633] [Example 88] Compound (4)-1-12 was obtained (yield 86%) in the same manner as in Example 77, except that compound (40)-1-10 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-12 was confirmed by NMR, and the data are shown below. 1H NMR (400 MHz, CDCl3, ppm) δ 7.29-7.36 (m, 4H), 7.17-7.21 (m, 2H), 5.19 (s, 1H), 1.13 (s, 9H), 0.27 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 205.8, 138.2, 128.3, 127.3, 125.9, 101.8, 99.4, 32.1, 30.6, -0.2.

[0634] [ka]

[0635] [Example 89] Compound (4)-1-13 was obtained (yield 83%) in the same manner as in Example 77, except that compound (40)-1-1 (0.3 mmol) was replaced with compound (40)-1-11 (0.3 mmol). The structure of compound (4)-1-13 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.13 (d, J = 8.0 Hz, 2H), 7.09 (d, J = 8.0 Hz, 2H), 5.86 (t, J = 2.8 Hz, 1H), 2.33 (s, 3H), 2.09-2.13 (m, 2H), 1.46-1.54 (m, 2H), 1.37 (q, J = 7.6 Hz, 2H), 0.90 (t, J = 7.2 Hz, 3H), 0.16 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 206.5, 136.6, 134.5, 130.5, 126.9, 102.4, 90.9, 32.8, 30.6, 23.9, 22.4, 15.3, 0.04.

[0636] [ka]

[0637] [Example 90] Compound (4)-1-14 was obtained (yield 84%) in the same manner as in Example 77, except that compound (40)-1-12 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-14 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ, 4.81 (t, J = 7.2 Hz, 1H), 1.93-1.97 (m, 2H), 1.35-1.45 (m, 4H), 1.09 (s, 9H), 0.90 (t, J = 7.2 Hz, 3H), 0.08 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 202.6, 98.5, 98.0, 31.5, 31.4, 30.7, 29.3, 22.6, 14.0, -1.4.

[0638] [ka]

[0639] [Example 91] Compound (4)-1-15 was obtained (yield 70%) in the same manner as in Example 77, except that compound (40)-1-13 (0.3 mmol) was used instead of compound (40)-1-1 (0.3 mmol). The structure of compound (4)-1-15 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 4.32 (t, J = 3.2Hz, 2H), 1.98-1.92 (m, 2H), 1.47-1.34 (m, 4H), 0.91 (t, J = 7.2Hz, 3H), 0.10 (s, 9H); 13C NMR(100 MHz, CDCl3, ppm) δ 208.2, 94.5, 68.7, 31.3, 28.4, 22.5, 14.0, -1.5.

[0640] [ka]

[0641] <<Production of compound (5)>> [Example 92] Under an argon gas atmosphere, compound (50)-1-1 (0.3 mmol) and compound (9)-1-1 (0.9 mmol) were dissolved in toluene (1.0 mL), and the compound (Au / ZrO2) obtained above (amount so that the amount of gold was 0.009 mmol) was suspended as a catalyst. The resulting mixture was stirred at 100 °C for 3 hours to cause a reaction. Thereafter, the same method as in Example 1 was used to obtain compound (5)-1-1 (yield 67%). The structure of compound (5)-1-1 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 5.25-5.49 (m, 2H), 1.94-2.07 (m, 4H), 1.27-1.36 (m, 12H), 0.89 (t, J = 7.0 Hz, 3H), 0.55-0.60 (m, 2H), 0.01 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 133.0, 128.9, 32.5, 31.9, 29.7, 29.5, 29.3, 29.3, 26.9, 22.7, 16.6, 14.1, -1.6.

[0642] [ka]

[0643] [Example 93] Compound (5)-1-2 was obtained (yield 75%) in the same manner as in Example 92, except that compound (50)-1-2 (0.3 mmol) was used instead of compound (50)-1-1 (0.3 mmol) and the stirring time of the mixture (in other words, the reaction time) was changed from 3 hours to 2 hours. The structure of compound (5)-1-2 was confirmed by NMR, and the data are shown below. 1 H NMR (400 MHz, CDCl3, ppm) δ 7.18-7.36 (m, 5H), 6.25-6.41 (m, 2H), 2.22-2.28 (m, 2H), 0.70-0.74 (m, 2H), 0.05 (s, 9H); 13 C NMR (100 MHz, CDCl3, ppm) δ 138.0, 133.8, 128.4, 128.3, 126.6, 125.9, 27.4, 16.3, -1.6.

[0644] [ka]

[0645] <<Production of Compound (1) (Reuse of Catalyst)>> [Example 94] Compound (1)-1-2 was produced (yield 99%) using compound (10)-1-2 (0.3 mmol), compound (9)-1-1 (0.9 mmol), and compound (Au / ZrO) (amount equivalent to 0.009 mmol of gold) in the same manner as in Example 15. The entire compound (Au / ZrO) was removed from the reaction solution. The removed compound (Au / ZrO) was washed three times with an excess amount of diethyl ether and dried under reduced pressure at 80°C. Next, using this recovered compound (Au / ZrO2), compound (1)-1-2 was produced under the same conditions as before (yield 99%), and the entire amount of compound (Au / ZrO2) was extracted from the reaction solution, washed three times, and dried under reduced pressure. Furthermore, the compound (Au / ZrO2) recovered twice was used to produce compound (1)-1-2 three times under the same conditions, with yields of compound (1)-1-2 of 97%, 92%, and 99%, respectively. Thus, it was confirmed that compound (1) can be successfully produced even when compound (Au / ZrO2) is repeatedly reused as a catalyst.

[0646] [ka]

[0647] <<Production of Compound (4) (Reuse of Catalyst)>> [Example 95] Using the same method as in Example 77, compound (4)-1-1 was produced (yield 90%) using compound (40)-1-1 (0.3 mmol), compound (9)-1-1 (0.9 mmol), and compound (Au / ZrO2) (amount equivalent to 0.009 mmol of gold). The entire amount of compound (Au / ZrO2) was removed from the reaction solution. The removed compound (Au / ZrO2) was then washed three times with an excess amount of diethyl ether and dried under reduced pressure at 80 °C. Next, using this recovered compound (Au / ZrO2), compound (4)-1-1 was produced under the same conditions as before (yield 91%), and the entire amount of compound (Au / ZrO2) was extracted from the reaction solution, washed three times, and dried under reduced pressure. Furthermore, the compound (Au / ZrO2) recovered twice was used to produce compound (4)-1-1 four times under the same conditions, with yields of compound (4)-1-1 of 90%, 91%, 82%, and 93%, respectively. Thus, it was confirmed that compound (4) can be successfully produced even when compound (Au / ZrO2) is repeatedly reused as a catalyst.

[0648] [ka] [Industrial Applicability]

[0649] The present invention can be used to produce organosilicon compounds, and when polyester is used as a raw material for producing the organosilicon compound, it is possible to decompose the polyester simultaneously with the production of the organosilicon compound.

Claims

1. The following general formula (10) 【Chemistry 1】 (In the formula, n １０ is an integer equal to or greater than 1; R １１ and R １２ are each independently a hydrogen atom or a hydrocarbon group which may have a substituent, provided that R １１ and R １２ At least one of is a hydrogen atom, and n １０ When n is 2 or more, １０ R １１ may be the same or different, and n １０ R １２ may be the same or different from each other; Z １１ is a hydrocarbon group which may have a substituent, and R １１ When is the hydrocarbon group which may have a substituent, Z １１ and R １１ may be bonded to each other to form a ring; X １１ is represented by the following general formula (101): 【Chemistry 2】 (In the formula, R １３ represents an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a dialkylamino group; a bond marked with an asterisk (*) represents X １１ is formed with respect to the carbon atom to which the following general formula (102) 【Transformation 3】 (In the formula, R １４ represents an alkyl group, an aryl group, or an aralkyl group; a bond marked with an * represents X １１ is formed relative to the carbon atom to which n is bonded. １０ When n is 2 or more, １０ X of pieces １１ may be the same or different from each other, and The following general formula (9) 【Chemistry 4】 (In the formula, R ９１ is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R ９１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (1): 【Transformation 5】 (In the formula, n １０ , R １１ , R １２ , Z １１ and R ９１ is the same as above, and n １０ When n is 2 or more, １０ The general formula "-SiR ９１ ３ " may be the same or different from each other.) or a compound represented by the following general formula (1'): 【Transformation 6】 (In the formula, n １１ and n １２ are each independently an integer of 1 or more, provided that n １１ +n １２ = n １０ (≧2); n １０ , R １１ , R １２ , Z １１ , X １１ and R ９１ is the same as above; n １１ When n is 2 or more, １１ R １１ may be the same or different, and n １１ R １２ may be the same or different, and n １１ The general formula "-SiR ９１ ３ " may be the same or different; n １２ When n is 2 or more, １２ R １１ may be the same or different, and n １２ R １２ may be the same or different, and n １２ X of pieces １１ may be the same or different from each other, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

2. The following general formula (20) 【Transformation 7】 (In the formula, Z ２１ is a hydrocarbon group which may have a substituent, and a carbon atom in the hydrocarbon group may be substituted with a nitrogen atom together with a hydrogen atom bonded to the carbon atom, The following general formula (9) 【Transformation 8】 (In the formula, R ９１ is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R ９１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (2): 【Chemistry 9】 (In the formula, Z ２１ and R ９１ is the same as above, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

3. The following general formula (30) 【Chemistry 10】 (In the formula, l １ is an integer equal to or greater than 2; l ２ is 0 or 1; R ３１ is an alkylene group, and one or more methylene groups in the alkylene group may be substituted with an arylene group; １ R ３１ may be the same or different from each other; R ３２ is an alkylene group or an arylene group, ２ If is 1, then l １ R ３２ may be the same or different from each other; wherein the terminal carboxy group may form a salt, and The following general formula (9) 【Chemistry 11】 (In the formula, R ９１ is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R ９１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (3): 【Chemistry 12】 (In the formula, R ３１ and R ９１ is the same as above, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

4. The following general formula (40) 【Chemistry 13】 (In the formula, R ４１ and R ４２ are each independently a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group, and R ４１ and R ４２ When both are the alkyl group, R ４１ and R ４２ may be bonded to each other to form a ring; R ４３ is an alkyl group, an aryl group, an aralkyl group, a trialkylsilyl group, or a dialkylarylsilyl group; R ４４ is an alkyl group, an aryl group, or an aralkyl group; The following general formula (9) 【Chemistry 14】 (In the formula, R ９１ is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R ９１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (4): 【Chemistry 15】 (In the formula, R ４１ , R ４２ , R ４３ and R ９１ is the same as above, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

5. The following general formula (50) 【Chemistry 16】 (In the formula, R ５１ is a hydrogen atom, an alkyl group, an aryl group, or an aralkyl group; R ５２ is an alkyl group, an aryl group, or an aralkyl group; The following general formula (9) 【Chemistry 17】 (In the formula, R ９１ is an alkyl group, an aryl group, an aralkyl group, an alkoxy group, an aryloxy group, an aralkyloxy group, or a trialkylsilyloxy group, and six R ９１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (5): [Chemistry 18] (In the formula, R ５１ and R ９１ is the same as above, The method for producing a compound, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

6. The following general formula (10)-1 【Chemistry 19】 (In the formula, R １１１ and R １２１ are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R １１１ and R １２１ at least one of is a hydrogen atom; Z １１１ represents an alkyl group, alkenyl group, or alkynyl group having 3 to 12 carbon atoms which may have a substituent, an aryl group having 6 to 12 carbon atoms which may have a substituent, an aralkyl group having 7 to 13 carbon atoms which may have a substituent, or an arylalkenyl group having 8 to 14 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R １１１ When is the alkyl group having 1 to 7 carbon atoms, Z １１１ and R １１１ may be bonded to each other to form a ring; X １１１ is represented by the following general formula (101)-1 【Chemistry 20】 (In the formula, R １３１ represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X １１１ is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102)-1 【Chemistry 21】 (In the formula, R １４１ represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X １１１ is formed with respect to the carbon atom to which The following general formula (9)-1 【Chemistry 22】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to obtain a compound represented by the following general formula (1)-1 【Chemistry 23】 (In the formula, R １１１ , R １２１ , Z １１１ and R ９１１ is the same as above, The method for producing a compound according to claim 1 , wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

7. The following general formula (10)-2 【Chemistry 24】 (In the formula, R １１２ and R １２２ are each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms, provided that R １１２ and R １２２ At least one of R is a hydrogen atom, １１２ may be the same or different, and two R １２２ may be the same or different from each other; Z １１２ represents an alkylene group, alkenylene group, or alkynylene group having 3 to 12 carbon atoms which may have a substituent, or an arylene group having 6 to 12 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R １１２ When is the alkyl group having 1 to 7 carbon atoms, Z １１２ and R １１２ may be bonded to each other to form a ring; X １１２ is represented by the following general formula (101)-2 【Chemistry 25】 (In the formula, R １３２ represents an alkyl group or alkoxy group having 1 to 12 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group or aralkyloxy group having 7 to 13 carbon atoms, or a dialkylamino group having 2 to 4 carbon atoms; and the bond marked with * represents X １１２ is formed with respect to the carbon atom to which the following is bonded.) a group represented by the following general formula (102)-2 【Chemistry 26】 (In the formula, R １４２ represents an alkyl group having 1 to 12 carbon atoms or an aryl group having 6 to 10 carbon atoms; a bond marked with an * represents X １１２ is formed with respect to the carbon atom to which The following general formula (9)-1 【Chemistry 27】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to obtain a compound represented by the following general formula (1)-2 【Chemistry 28】 (In the formula, R １１２ , R １２２ , Z １１２ and R ９１１ is the same as above, The method for producing a compound according to claim 1 , wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

8. The following general formula (20)-1 【Chemistry 29】 (In the formula, m １ is an integer from 1 to 5; R ２１１ and R ２１２ each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; １ When m is 2 or more, １ R ２１１ may be the same or different, m １ R ２１２ may be the same or different, and R ２１１ and R ２１２ is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R ２１１ and R ２１２ may be bonded to each other to form a ring, m １ are two or more and are bonded to adjacent carbon atoms ２１１ Comrades or R ２１２ When both of them are the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, the R ２１１ or the above R ２１２ may be bonded to each other to form a ring, and R ２１１ and R ２１２ When either or both of R ２１１ and R ２１２ may be replaced with a nitrogen atom, together with the hydrogen atom attached to said carbon atom; m ２ is 0 or 1; R ２１３ and R ２１４ each independently represents a hydrogen atom, an alkyl group having 1 to 7 carbon atoms which may have a substituent, an alkenyl group having 2 to 7 carbon atoms which may have a substituent, or an aryl group having 6 to 10 carbon atoms which may have a substituent, wherein the substituent is one or more selected from the group consisting of a fluorine atom, a chlorine atom, a bromine atom, a 1-indolyl group, an alkenyl group having 2 to 6 carbon atoms, a fluorinated or chlorinated alkyl group having 1 to 3 carbon atoms, an acyloxy group having 2 to 4 carbon atoms, and a 4,4,5,5-tetramethyl-[1,3,2]-dioxaborolanyl group; R ２１３ and R ２１４ is the alkyl group having 1 to 7 carbon atoms which may have a substituent, or the alkenyl group having 2 to 7 carbon atoms which may have a substituent, R ２１３ and R ２１４ may be bonded to each other to form a ring, The following general formula (9)-1 【Transformation 30】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (2-1 【Chemistry 31】 (In the formula, m １ , m ２ , R ２１１ , R ２１２ , R ２１３ , R ２１４ and R ９１１ is the same as above, The method for producing a compound according to claim 2, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

9. The following general formula (30)-1 【Chemistry 32】 (In the formula, l １１ is an integer equal to or greater than 2; l ２１ is 0 or 1; R ３１１ is an alkylene group having 2 to 8 carbon atoms, and one or more methylene groups in the alkylene group may be substituted with an arylene group; １１ R ３１１ may be the same or different from each other; R ３２１ is an alkylene group having 2 to 6 carbon atoms or an arylene group having 6 to 12 carbon atoms, ２１ If is 1, then l １１ R ３２１ may be the same or different from each other; wherein the terminal carboxy group may form a salt, and The following general formula (9)-1 【Transformation 33】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to form a compound represented by the following general formula (3-1) 【Transformation 34】 (In the formula, R ３１１ and R ９１１ is the same as above, The method for producing a compound according to claim 3 , wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

10. The following general formula (40)-1 【Chemistry 35】 (In the formula, R ４１１ and R ４２１ are each independently a hydrogen atom, an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms; R ４１１ and R ４２１ When both are the alkyl group, R ４１１ and R ４２１ may be bonded to each other to form a ring; R ４３１ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, an aralkyl group having 7 to 13 carbon atoms, a trialkylsilyl group having 3 to 8 carbon atoms, or a dialkylarylsilyl group having 8 to 10 carbon atoms; R ４４１ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms; The following general formula (9)-1 【Transformation 36】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to obtain a compound represented by the following general formula (4)-1 【Chemistry 37】 (In the formula, R ４１１ , R ４２１ , R ４３１ and R ９１１ is the same as above, The method for producing a compound according to claim 4, wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

11. The following general formula (50)-1 【Transformation 38】 (In the formula, R ５１１ is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms; R ５２１ is an alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, or an aralkyl group having 7 to 13 carbon atoms; The following general formula (9)-1 【Chemistry 39】 (In the formula, R ９１１ is an alkyl group or alkoxy group having 1 to 4 carbon atoms, an aryl group or aryloxy group having 6 to 10 carbon atoms, an aralkyl group having 7 to 12 carbon atoms, or a trialkylsilyloxy group having 3 to 6 carbon atoms, and six R ９１１ may be the same or different from each other, and in the presence of a catalyst to obtain a compound represented by the following general formula (5-1) 【Chemistry 40】 (In the formula, R ５１１ and R ９１１ is the same as above, The method for producing a compound according to claim 5 , wherein the catalyst is a compound in which gold is supported on a metal oxide, a metal oxoacid salt, or carbon.

12. The method for producing the compound according to any one of claims 1 to 11, further comprising recovering the catalyst used in the reaction step after the reaction step, and then performing the reaction step again using the recovered catalyst, a re-reaction step being performed one or more times.

13. The method for producing a compound according to any one of claims 1 to 12, wherein the catalyst is a compound in which gold is supported on zirconium oxide, titanium oxide, diiron trioxide, triiron tetroxide, aluminum oxide, yttrium oxide, gallium oxide, zirconium pyrophosphate, dichromium trioxide, or carbon.

14. The following general formula (1) 【Chemistry 41】 (In the formula, n １０ is 1; R １１ and R １２ is a hydrogen atom; R ９１ is an alkyl group having 1 to 6 carbon atoms or an alkoxy group having 1 to 6 carbon atoms, and is represented by the general formula "-SiR ９１ ３ " Three R's in ９１ may be the same or different from each other; Z １１ is an alkyl group having 3 to 12 carbon atoms and having a 1-indolyl group as a substituent, or an aryl group having 6 to 12 carbon atoms and having a fluorine atom, a chlorine atom, a bromine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, or an acyloxy group having 2 to 4 carbon atoms as a substituent.

15. The following general formula (2) 【Chemistry 42】 (In the formula, Z ２１ is a linear alkenylene group having 3 to 12 carbon atoms, —CH 2 —C 6 H 4 — (wherein —C 6 H 4 — is bonded to the oxygen atom in general formula (2)), or a branched alkylene group having 3 to 12 carbon atoms and having as a substituent a fluorine atom, a chlorine atom, a bromine atom, a fluorinated alkyl group having 1 to 3 carbon atoms, a chlorinated alkyl group having 1 to 3 carbon atoms, a cyano group, or an acyloxy group having 2 to 4 carbon atoms; R ９１ is an alkyl group having 1 to 12 carbon atoms or an alkoxy group having 1 to 12 carbon atoms, and six R ９１ may be the same or different.

16. The following general formula (4) 【Chemistry 43】 (wherein R 41 , R 42 and R 43 each independently represent a chain alkyl group having 1 to 12 carbon atoms; one of R 41 and R 42 is a hydrogen atom, and the other is a chain alkyl group having 1 to 12 carbon atoms or an aralkyl group having 7 to 27 carbon atoms, and R 43 is an aryl group having 6 to 15 carbon atoms; or one of R 41 and R 42 is a hydrogen atom, and the other is an aryl group having 6 to 15 carbon atoms; R 43 is an alkyl group having 1 to 12 carbon atoms; and, R ９１ is an alkyl group having 1 to 12 carbon atoms, and three R ９１ may be the same or different.

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