Iron complex compound and method for producing same, and method for producing organosilicon compound

Abstract

The present invention provides a novel hydrosilylation catalyst which uses inexpensive and abundant iron, and is suitable for use in organosilicon industries.　Provides is an iron complex compound represented by formula (1): (L)FeAn1. (In the formula, n1 represents 2 or 3, and each A independently represents -OR1, -OC(=O)R2, or -NR3R4; R1, R2, R3, and R4 each independently represent an optionally substituted hydrocarbon group having 13 to 24 carbon atoms, or -Si(CH3)2-[OSi(CH3)2]m-CH3, and m represents an integer of 0 to 11; in cases where two A moieties are each -OR1 and R1 is an optionally substituted hydrocarbon group having 13 to 24 carbon atoms, the R1 moieties may be linked to each other to form a cyclic structure -O-C(Ra)-O-, and Ra represents an optionally substituted hydrocarbon group having 13 to 24 carbon atoms; and L represents a tridentate ligand which has a specific structure.)

Description

Iron complex compound, method for producing the same, and method for producing organosilicon compound

[0001] The present invention relates to an iron complex compound and a method for producing the same, and a method for producing an organosilicon compound.

[0002] In the organosilicon industry, hydrosilylation catalysts are widely used in the production of cured silicone materials and organosilicon compounds. Hydrosilylation catalysts cleave the silicon-hydrogen bond of hydrosilanes and catalyze the addition reaction of alkenes to carbon-carbon unsaturated bonds. Industrial platinum catalysts, such as Karstedt's catalyst, have long been used as hydrosilylation catalysts. While platinum catalysts are highly active, they are expensive, have supply issues, and suffer from poor selectivity and difficult recovery. Therefore, there is a need for technologies to replace platinum with other metals. In recent years, efforts have been made to develop hydrosilylation catalysts using inexpensive and abundant iron. One known iron-based hydrosilylation catalyst is an iron complex compound with a bisiminopyridine ligand, developed by PJ Chirik et al. (Non-Patent Document 1). However, this catalyst is unstable in air and difficult to handle. An iron complex compound with a tridentate ligand, developed by the present inventors, is known as an iron catalyst with improved air stability (Patent Documents 1 and 2, Non-Patent Document 2). The iron complex compound having a tridentate ligand exhibits high catalytic activity in hydrosilylation reactions and is highly practical in that it can be handled in air.

[0003] JP 2020-117474 A JP 2020-50637 A

[0004] PJ Chirik et. al. Science 2012, 335, 567-570M. Kamitani, Chem. Commun. 2021, 57, 13246-13258Kamitani, M.; Kusaka, H.; Toriyabe, T.; Yuge, H., Bull. Chem. Soc. Jpn., 2018, 91, 1429-1435.Britovsek,GJP; Gibson,VC; McTavish,SJ; Solan, GA; White, AJP; Williams,DJ; Britovsek,GJP; Kimberley,BS;Maddox,PJ Chem. Commun. 1998, 849-850.Kamitani, M.; Yujiri, K.; Yuge, H.Organometallics 2020, 39, 3535-3539Kamitani, M.; Kanemitsu, K.; Yujiri, K.; Yuge, H. Organometallics 2023, 42, 1839-1848

[0005] There is a need for further development of hydrosilylation catalysts that utilize inexpensive and abundant iron for use in the organosilicon industry.

[0006] The present invention includes the following embodiments and aspects: [1] Formula (1): (L)FeA ｎ１ (1) [wherein, n1 is 2 or 3, and each A is independently -OR １ , —OC(═O)R ２ , or -NR ３ R ４ and R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３and m is an integer of 0 to 11; and two A's are -OR １ and R １ is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, R １ They are linked together to form a cyclic structure -O-C(R ａ ) —O—, and R ａ represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent; L represents a group represented by formula (L-1): [In the formula, R ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R ７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer of 0 to 4, provided that R ５ is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ is bonded to a carbon atom of the quinoline skeleton.] or Formula (L-2): [In the formula, R ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R１１ may be linked to form a cyclic structure, and R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer of 0 to 3, provided that R ９ represents a tridentate ligand represented by the formula (1A-1), (1A-2), or (1A-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ａ , n2, and n3 are as defined above.] [3] The iron complex compound according to the above item [1], represented by formula (1B-1), (1B-2), or (1B-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ９ , R １０ , R １１ , R １２ , R １３ , R ａ and n4 are as defined above.] [4] The iron complex compound according to the above [1], represented by formula (1a-1): [In the formula, X １ and X ２ are each independently a halogen atom; ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R ７and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer of 0 to 4, provided that R ５ is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ is bonded to a carbon atom of the quinoline skeleton.] and an iron compound represented by the formula: １ O.M., R. ２ COOM or NR ３ R ４ M (1a-2) [wherein, R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ [5] A method for producing the iron complex compound according to the above [1] or [2], comprising reacting a compound represented by formula (1b-1): [In the formula, X １ and X ２ are each independently a halogen atom; ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１may be linked to form a cyclic structure, and R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer of 0 to 3, provided that R ９ is bonded to a carbon atom of the pyridine skeleton.] and an iron compound represented by the formula: １ O.M., R. ２ COOM or NR ３ R ４ M (1b-2) [wherein, R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ wherein m is an integer of 0 to 11; and each M is independently an alkali metal.] with a compound represented by the following formula: [6] A method for producing an organosilicon compound, comprising reacting an alkene with a hydrosilane in the presence of the iron complex compound according to [1], [2], or [3].

[0007] The iron complex compound of the present invention is a novel iron-based hydrosilylation catalyst that can be suitably used in the organosilicon industry, particularly in the production of cured silicone materials and organosilicon compounds. Because the iron complex compound of the present invention has high solubility in silicone, it is particularly suitable for applications using silicone as a raw material. According to a preferred embodiment of the present invention, organosilicon compounds and cured silicone materials can be produced efficiently.

[0008] The present invention will be specifically described below.

[0009] 1. Iron Complex Compound The iron complex compound according to one embodiment of the present invention is represented by the formula (1): (L)FeA ｎ１(1) [wherein L, A, and n1 are as defined above.] The iron complex compound according to this aspect includes an iron complex compound in which the ligand L is represented by formula (L-1) (first embodiment) and an iron complex compound in which the ligand L is represented by formula (L-2) (second embodiment). Each embodiment will be described below.

[0010] First Embodiment The iron complex compound according to the first embodiment has the following formula: (L １ ) FeA ｎ１ (1A) wherein n1 is 2 or 3, and each A is independently -OR １ , —OC(═O)R ２ , or -NR ３ R ４ and R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ and m is an integer of 0 to 11; and two A's are -OR １ and R １ is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, R １ They are linked together to form a cyclic structure -O-C(R ａ ) —O—, and R ａ represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent; １ is represented by formula (L-1): [In the formula, R ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer of 0 to 4, provided that R ５ is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ represents a tridentate ligand represented by the formula: ] which is bonded to a carbon atom of the quinoline skeleton. ]

[0011] In the formula, n1 is 2 or 3. When n1 is 2, the coordination number of the iron complex compound according to this embodiment is 5, and when n1 is 3, the coordination number of the iron complex compound according to this embodiment is 6.

[0012] Each A is independently -OR １ , —OC(═O)R ２ , or -NR ３ R ４ and R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer from 0 to 11.

[0013] R １ , R ２ , R ３ , and R ４The hydrocarbon group may be a saturated or unsaturated hydrocarbon group, and may be any of a chain hydrocarbon group, an alicyclic hydrocarbon group, or an aromatic hydrocarbon group, and if it is a chain hydrocarbon group, it may be either a straight chain or a branched chain. In terms of solubility in silicone, a saturated or unsaturated chain hydrocarbon group is preferred, and a straight chain hydrocarbon group is more preferred. As the chain hydrocarbon group, an alkyl group or an alkenyl group is preferred, and an alkyl group is more preferred. The number of carbon atoms in the hydrocarbon group is 13 to 24, preferably 14 to 20, more preferably 16 to 20, and even more preferably 16 to 18. When the number of carbon atoms in the hydrocarbon group is within this range, solubility in silicone can be increased.

[0014] Examples of alkyl groups include tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, eicosyl, heniicosyl, docosyl, tricosyl, and tetracosyl groups. These may be linear or branched, but linear is preferred. Examples of alkenyl groups include tridecenyl, tetradecenyl, pentadecenyl, hexadecenyl, heptadecenyl, octadecenyl, nonadecenyl, icosenyl, eicosenyl, heniicosenyl, docosenyl, tricosenyl, and tetracosenyl groups. Each of these groups has a double bond at any position. These may be linear or branched, but linear is preferred.

[0015] The hydrocarbon group may have a substituent at any position. When multiple substituents are present, they may be the same or different and may be bonded to each other to form a ring together with the atoms to which they are bonded. Examples of the substituent include a halogen atom, an amino group which may have a substituent, an amide group, an alkoxyl group, a hydroxyl group, a carboxyl group, a carbonyl group, a silyl group, and the like. Examples of the halogen atom include fluorine, chlorine, bromine, and iodine. Examples of the alkoxyl group include an alkoxyl group having 1 to 10 carbon atoms, specifically, a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a tert-butoxy group, and the like. Examples of the amino group which may have a substituent include an amino group and a dialkylamino group having 1 to 18 carbon atoms, specifically, a dimethylamino group, a didodecylamino group, and the like. In addition, -CH contained in the hydrocarbon group ２ - is -O-, -S-, -SO ２ At least one bond of -, -CO-, -COO-, -CONH- and -NH- may be replaced by this.

[0016] R １ , R ２ , R ３ , and R ４ is -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer of 0 to 11, preferably 0 to 10, more preferably 0 to 4, and even more preferably 0 to 1. For example, —Si(CH ３ ) ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ]-CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ２ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH３ ) ２ ] ３ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ４ -CH ３ is more preferred.

[0017] A is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ By having the above formula, the solubility of the iron complex compound in silicone can be improved.

[0018] In one embodiment, R １ , R ２ More preferably, R is each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent. ３ , R ４ Each of the groups independently represents —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ is more preferred.

[0019] In addition, the two A's are -OR １ and R １ is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, R １ They are linked together to form a cyclic structure -O-C(R ａ )-O- may be formed. ａ R is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent. ａ The hydrocarbon group and the substituent that the hydrocarbon group may have are R １ , R ２ , R ３ , and R ４ The hydrocarbon group and the substituent have the same meanings as those described above, and preferred examples thereof are also the same.

[0020] In the formula (1A), L １ represents a tridentate ligand represented by formula (L-1).

[0021] In the formula (L-1), R ５ and R ６ R each independently represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom. ５ and R ６ Examples of the halogen atom in R include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. ５ and R ６ The aliphatic hydrocarbon group in may be a saturated or unsaturated aliphatic hydrocarbon group, and is preferably an alkyl group or an alkenyl group, more preferably an alkyl group. Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a pentyl group, a hexyl group, and a cyclohexyl group. ５ and R ６ Examples of the substituent that the aliphatic hydrocarbon group in R may have include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. ５ and R ６ The aromatic hydrocarbon group in R is a monocyclic or polycyclic aromatic hydrocarbon group, and examples thereof include a phenyl group, a 2,6-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,6-diisopropylphenyl group, and a naphthyl group. ５ and R ６ Examples of the substituent that the aromatic hydrocarbon group in R may have include an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group, an alkoxyl group, a silyl group, and a halogen atom, and a specific example is an alkyl group having 1 to 6 carbon atoms. Specific examples of the aliphatic hydrocarbon group having 1 to 6 carbon atoms, the aromatic hydrocarbon group, and the halogen atom include those explained above. Examples of the alkoxyl group include an alkoxyl group having 1 to 10 carbon atoms, and specific examples include a methoxy group, an ethoxy group, a propoxy group, a butoxy group, and a tert-butoxy group. R ５ and R６ Examples of the aromatic hydrocarbon group which may have a substituent include a phenyl group, a 2,6-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,6-diisopropylphenyl group, and a naphthyl group.

[0022] In the formula (L-1), R ７ and R ８ R each independently represents an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. ７ and R ８ The aliphatic hydrocarbon group in R may be a saturated or unsaturated aliphatic hydrocarbon group, and is preferably an alkyl group or an alkenyl group, more preferably an alkyl group. ７ and R ８ The alkyl group in R is not limited to a linear alkyl group, but also includes alkyl groups having a branched structure or a cyclic structure. Examples of alkyl groups having 1 to 12 carbon atoms, which may have a substituent, include a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, a t-butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, a decyl group, and a cyclohexyl group. ７ and R ８ Examples of the substituent that the aliphatic hydrocarbon group in R may have include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. ７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure. For example, R ７ and R ８ may be linked to form a phosphorane structure, a phosphinane structure, a phosphetane structure, etc. ７ and R ８ The aromatic hydrocarbon group in R is a monocyclic or polycyclic aromatic hydrocarbon group, and examples thereof include a phenyl group and a naphthyl group. ７ and R ８Examples of the substituent that the aromatic hydrocarbon group in R may have include an aliphatic hydrocarbon group having 1 to 6 carbon atoms, an aromatic hydrocarbon group, an alkoxyl group, a silyl group, and a halogen atom, and a specific example is an alkyl group having 1 to 6 carbon atoms. Specific examples of the aliphatic hydrocarbon group having 1 to 6 carbon atoms, the aromatic hydrocarbon group, the halogen atom, and the alkoxyl group include those explained above. ７ and R ８ Examples of the aromatic hydrocarbon group which may have a substituent include a phenyl group, a 2,6-dimethylphenyl group, a 2,4-dimethylphenyl group, a 2,4,6-trimethylphenyl group, a 2,6-diisopropylphenyl group, and a naphthyl group.

[0023] In the formula (L-1), n2 is an integer of 0 to 4, preferably an integer of 0 to 2, more preferably 0 or 1, and particularly preferably 0. n3 is an integer of 0 to 5, preferably an integer of 0 to 3, more preferably an integer of 0 to 2, and particularly preferably 0 or 1.

[0024] R in the formula (L-1) ５ is bonded to a carbon atom of the pyridine skeleton. ５ is bonded to a carbon atom of the pyridine skeleton, the state in which R is bonded to a carbon atom constituting the pyridine ring. ５ In the formula (L-1), n2 is an integer of 2 to 4, and R ５ is an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, R ５ The aliphatic hydrocarbon groups may be linked together to form a cyclic structure. For example, when n2 is 2, two R ５ are linked to form a cycloheptane structure, a cycloheptene structure, a cyclohexane structure, a cyclohexene structure, etc.

[0025] R in the formula (L-1) ６ is bonded to a carbon atom of the quinoline skeleton. ６ is bonded to a carbon atom of the quinoline skeleton, the carbon atom constituting the quinoline ring is bonded to a carbon atom of the quinoline skeleton. ６ In the formula (L-1), n3 is an integer of 2 to 5, and R６ is an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, R ６ For example, when n3 is 2, two R ６ are linked to form a cycloheptane structure, a cycloheptene structure, a cyclohexane structure, a cyclohexene structure, etc.

[0026] Specific examples of the iron complex compound of the first embodiment include those represented by the following formula (1A-1), (1A-2), or (1A-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ａ , n2, and n3 are as defined above.]

[0027] Among these iron complex compounds, particularly preferred iron complex compounds include the following compounds. [In the formula, R １ , R ２ , R ３ , R ４ , R ６ , R ７ , R ８ , and R ａ is as defined above.]

[0028] Among them, in the formula (1A-1′), R ａ is preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. ２is preferably a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, and even more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. When it is a chain hydrocarbon group, it may be either a straight chain or branched chain, but is preferably a straight chain.

[0029] In addition, in the formula (1A-2′), R １ are each independently preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. Alternatively, R １ are each independently —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer of 0 to 11, preferably 0 to 10, more preferably 0 to 4, and even more preferably 0 to 1. For example, —Si(CH ３ ) ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ]-CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ２ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ３ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ４ -CH ３ is more preferred.

[0030] In addition, in the formula (1A-3′), R ３ and R ４ are each independently preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. Alternatively, R ３ and R ４ are each independently —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer of 0 to 11, preferably 0 to 10, more preferably 0 to 4, and even more preferably 0 to 1. For example, —Si(CH ３ ) ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ]-CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ２ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ３ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ４ -CH ３ is more preferred.

[0031] Second Embodiment The iron complex compound according to the second embodiment has the following formula: (L ２ ) FeA ｎ１ (1B) [wherein n1 is 2 or 3, and each A is independently -OR １ , —OC(═O)R ２ , or -NR３ R ４ and R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ and m is an integer of 0 to 11; and two A's are -OR １ and R １ is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, R １ They are linked together to form a cyclic structure -O-C(R ａ ) —O—, and R ａ represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent; ２ is represented by formula (L-2): [In the formula, R ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１ may be linked to form a cyclic structure, and R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer of 0 to 3, provided that R ９ represents a tridentate ligand represented by the formula: ] which is bonded to a carbon atom of the pyridine skeleton. ]

[0032] In the formula, n1, A, R １ , R ２ , R ３ , R ４ , and R ａ are respectively n1, A, and R in the first embodiment. １ , R ２ , R ３ , R ４ , and R ａ The same can be mentioned as preferred examples.

[0033] In the formula (1B), L ２ represents a tridentate ligand represented by formula (L-2).

[0034] In the formula (L-2), n4 is an integer of 0 to 3, preferably 0 or 1, and particularly preferably 0. In the formula (L-2), R ９ R each independently represents an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom. ９ The aliphatic hydrocarbon group having 1 to 6 carbon atoms, which may have a substituent, the aromatic hydrocarbon group having 6 to 12 carbon atoms, which may have a substituent, or the halogen atom may be R ５ and R ６ Examples of the groups include the same groups as those exemplified in .

[0035] R in the formula (L-2) ９ is bonded to a carbon atom of the pyridine skeleton. ９ is bonded to a carbon atom of the pyridine skeleton, the state in which R is bonded to a carbon atom constituting the pyridine ring. ９ In the formula (L-2), n4 is 2 or 3, and R ９ is an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, R ９ The aliphatic hydrocarbon groups may be linked together to form a cyclic structure. For example, when n4 is 2, two R ９ may be linked to form a cycloheptane structure, a cycloheptene structure, a cyclohexane structure, a cyclohexene structure, or the like.

[0036] In the formula (L-2), R １０ , R １１ , R １２ and R １３ R each independently represents a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent. １０ , R １１ , R １２ and R １３ Examples of the aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent and the aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent include R ７ and R ８ The same groups as those exemplified in R １０ and R １２ R are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. １１ and R １３ are each independently preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, and more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms. １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１ may be linked to form a cyclic structure, R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure. For example, R １０ and R １１ , R １２ and R １３ may be linked to each other to form a pyrrole structure, a pyridine structure, or the like.

[0037] The iron complex compound of the second embodiment includes, for example, the iron complex compound represented by the following formula (1B-1), (1B-2), or (1B-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ９ , R １０ , R １１ , R １２ , R １３ , R ａ and n4 are as defined above.]

[0038] Among these iron complex compounds, particularly preferred iron complex compounds include the following compounds. [In the formula, R １ , R ２ , R ３ , R ４ , R １０ , R １１ , R １２ , R １３ , and R ａ is as defined above.]

[0039] Among them, in the formula (1B-1′), R ａ is preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. ２ is preferably a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, and even more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. When it is a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. １０ and R １２ R are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, more preferably an alkyl group or alkenyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. １１ and R １３are each independently preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, and more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms.

[0040] In addition, in the formula (1B-2′), R １ are each independently preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. Alternatively, R １ are each independently —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer of 0 to 11, preferably 0 to 10, more preferably 0 to 4, and even more preferably 0 to 1. For example, —Si(CH ３ ) ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ]-CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ２ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ３ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ４ -CH ３ is more preferred. １０ and R １２R are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. １１ and R １３ are each independently preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, and more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms.

[0041] In addition, in the formula (1B-3′), R ３ and R ４ are each independently preferably a saturated or unsaturated chain hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 13 to 24 carbon atoms which may have a substituent. In the case of a chain hydrocarbon group, it may be either a straight chain or a branched chain, but is preferably a straight chain. Alternatively, R ３ and R ４ are each independently —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ Here, m is an integer of 0 to 11, preferably 0 to 10, more preferably 0 to 4, and even more preferably 0 to 1. For example, —Si(CH ３ ) ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ]-CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ２ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ３ -CH ３ , -Si(CH ３ ) ２ -[OSi(CH ３) ２ ] ４ -CH ３ is more preferred. １０ and R １２ R are each independently preferably a hydrogen atom or an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, more preferably an alkyl or alkenyl group having 1 to 6 carbon atoms, and even more preferably an alkyl group having 1 to 6 carbon atoms. １１ and R １３ are each independently preferably a hydrogen atom or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, and more preferably an aromatic hydrocarbon group having 6 to 12 carbon atoms.

[0042] 2. Method for Producing Iron Complex Compound One aspect of the present invention for producing an iron complex compound includes a method for producing an iron complex compound having a tridentate ligand represented by formula (L-1) (first embodiment) and a method for producing an iron complex compound having a tridentate ligand represented by formula (L-2) (second embodiment). Each embodiment will be described below.

[0043] First Embodiment A method for producing an iron complex compound according to a first embodiment is a method for producing an iron complex compound represented by formula (1A), and the iron complex compound is represented by formula (1a-1): [In the formula, X １ and X ２ are each independently a halogen atom; ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R ７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer of 0 to 4, provided that R ５is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ is bonded to a carbon atom of the quinoline skeleton.] and an iron compound represented by the formula: １ O.M., R. ２ COOM or NR ３ R ４ M (1a-2) [wherein, R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ and m is an integer of 0 to 11; and each M is independently an alkali metal.

[0044] In formula (1a-1), X １ and X ２ are each independently a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. A chlorine atom or a bromine atom is preferred, and a chlorine atom is more preferred. In formula (1a-1), R ５ , R ６ , R ７ , R ８ , n2, and n3 are each R in formula (L-1). ５ , R ６ , R ７ , R ８ , n2, and n3, and preferred examples thereof are also the same.

[0045] The compound represented by formula (1a-1) can be produced by referring to the methods described in, for example, Kamitani, M.; Kusaka, H.; Toriyabe, T.; Yuge, H., Bull. Chem. Soc. Jpn., 2018, 91, 1429-1435. (Non-Patent Document 3), Britovsek, GJP; Gibson, VC; McTavish, SJ; Solan, GA; White, AJP; Williams, DJ; Britovsek, GJP; Kimberley, BS; Maddox, PJ Chem. Commun. 1998, 849-850. (Non-Patent Document 4).

[0046] Specifically, first, a tridentate ligand represented by the formula (L-1) is produced according to the methods described in Non-Patent Documents 3 and 4, and the obtained tridentate ligand is converted into a compound represented by the formula: FeX １ X ２ (In the formula, X １ and X ２ represents X in the formula (1a-1). １ and X ２ The compound represented by the formula (1a-1) can be produced by reacting the compound represented by the formula (1a-1) with an iron(II) halide represented by the formula (1a-2).

[0047] The reaction between the tridentate ligand and the iron(II) halide can be carried out in the presence or absence of a solvent, but is preferably carried out in the presence of a solvent because the reaction proceeds uniformly. The type of solvent is not particularly limited, but examples include hydrocarbon solvents such as hexane, heptane, octane, decane, dodecane, cyclohexane, methylcyclohexane, benzene, and toluene; and ether solvents such as diethyl ether, 1,4-dioxane, tetrahydrofuran (THF), and cyclopentyl methyl ether. Among these, tetrahydrofuran (THF), hexane, benzene, and toluene are preferred, with tetrahydrofuran being more preferred. The solvent may be used alone or in combination of two or more. The reaction temperature is preferably, for example, 0 to 80°C, more preferably 10 to 40°C, and more preferably room temperature. The reaction time is preferably, for example, 1 to 48 hours, more preferably 4 to 20 hours. The reaction can be carried out in an air atmosphere or an inert atmosphere such as nitrogen or argon, but is preferably carried out in an inert atmosphere such as nitrogen or argon. After the reaction is complete, the resulting solid is filtered, washed with a solvent, and then vacuum dried to obtain the target iron compound represented by formula (1a-1). Examples of the solvent used for washing include the same solvents as those exemplified for the reaction solvent.

[0048] In the first embodiment, the iron compound represented by the formula (1a-1) is reacted with the compound represented by the formula (1a-2) to produce the target iron complex compound represented by the formula (1A).

[0049] In the formula (1a-2), R １ , R ２ , R ３ , and R ４ are R in formula (1A) of "1. Iron complex compound" above. １ , R ２ , R ３ , and R ４ The same preferred examples are also given.

[0050] In the formula (1a-2), each M is independently an alkali metal, such as lithium, sodium, or potassium, with sodium or potassium being preferred.

[0051] The compound represented by the formula (1a-2) is generally known and can be easily obtained as a commercial product or by known synthesis methods.

[0052] The reaction of the iron compound represented by formula (1a-1) with the compound represented by formula (1a-2) can be carried out in the presence or absence of a solvent, but is preferably carried out in the presence of a solvent because the reaction proceeds uniformly. The type of solvent is not particularly limited, and examples thereof include hydrocarbon solvents such as hexane, heptane, octane, decane, dodecane, cyclohexane, methylcyclohexane, benzene, and toluene; and ether solvents such as diethyl ether, 1,4-dioxane, tetrahydrofuran, and cyclopentyl methyl ether. Among these, tetrahydrofuran, hexane, benzene, toluene, and diethyl ether are preferred, with tetrahydrofuran and diethyl ether being more preferred. The solvent may be used alone or in combination of two or more. For example, when the compound represented by formula (1a-2) has a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, it is preferred to use tetrahydrofuran, diethyl ether, benzene, or toluene as the solvent. Furthermore, for example, when the compound represented by formula (1a-2) is a -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ In this case, it is preferable to use diethyl ether, benzene, or toluene as the solvent.

[0053] The reaction temperature of the iron compound represented by formula (1a-1) and the compound represented by formula (1a-2) is, for example, preferably 0 to 80°C, more preferably 20 to 60°C. The reaction time is, for example, preferably 1 to 48 hours, more preferably 4 to 20 hours. The reaction can be carried out under an air atmosphere or an inert atmosphere such as nitrogen or argon, but is preferably carried out under an inert atmosphere such as nitrogen or argon. After completion of the reaction, insoluble matter is removed by filtration, and the mixture is then vacuum dried to obtain the target iron complex compound represented by formula (1A). The resulting compound may be purified by a conventional method before use. For example, the resulting compound may be dissolved in an appropriate solvent, filtered, and then vacuum dried or recrystallized to purify the filtrate. Examples of solvents used for the purification treatment include those exemplified as reaction solvents.

[0054] The iron complex compound represented by the formula (1A) may produce stereoisomers depending on the coordination mode or conformation of the ligand, and may be a mixture of these stereoisomers or a pure single isomer.

[0055] Second Embodiment A method for producing an iron complex compound according to a second embodiment is a method for producing an iron complex compound represented by the formula (1B), and the iron complex compound is represented by the formula (1b-1): [In the formula, X １ and X ２ are each independently a halogen atom; ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１may be linked to form a cyclic structure, and R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer of 0 to 3, provided that R ９ is bonded to a carbon atom of the pyridine skeleton.] and an iron compound represented by the formula: １ O.M., R. ２ COOM or NR ３ R ４ M (1b-2) [wherein, R １ , R ２ , R ３ , and R ４ are each independently a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or —Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ and m is an integer of 0 to 11; and each M is independently an alkali metal.

[0056] The method for producing an iron complex compound according to the second embodiment is the same as that according to the first embodiment, except that the iron compound represented by the formula (1b-1) is used as the iron compound.

[0057] X in the formula (1b-1) １ and X ２ are each independently a halogen atom. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. A chlorine atom or a bromine atom is preferred, and a chlorine atom is more preferred. In the formula (1b-1), R ９ , R １０ , R １１ , R １２ , R １３ , and n4 are R in the formula (L-2), respectively. ９ , R １０ , R １１ , R １２ , R １３, and n4, and preferred examples thereof are also the same.

[0058] The compound represented by formula (1b-1) can be produced, similarly to the compound represented by formula (1a-1), by referring to the methods described in, for example, Kamitani, M.; Kusaka, H.; Toriyabe, T.; Yuge, H., Bull. Chem. Soc. Jpn., 2018, 91, 1429-1435. (Non-Patent Document 3), Britovsek, GJP; Gibson, VC; McTavish, SJ; Solan, GA; White, AJP; Williams, DJ; Britovsek, GJP; Kimberley, BS; Maddox, PJ Chem. Commun. 1998, 849-850. (Non-Patent Document 4).

[0059] Specifically, first, a tridentate ligand represented by the formula (L-2) is produced according to the methods described in Non-Patent Documents 3 and 4, and the obtained tridentate ligand is converted into a compound represented by the formula: FeX １ X ２ (In the formula, X １ and X ２ represents X in the formula (1b-1). １ and X ２ The compound represented by the formula (1b-1) can be produced by reacting the compound represented by the formula (1b-2) with an iron(II) halide represented by the formula (1b-3).

[0060] The reaction between the tridentate ligand and the iron(II) halide can be carried out in the presence or absence of a solvent; however, it is preferable to carry out the reaction in the presence of a solvent, as this allows the reaction to proceed uniformly. The type of solvent is not particularly limited, and examples include the same solvents as those exemplified in the first embodiment. A single solvent may be used, or two or more solvents may be used in combination. The reaction temperature is preferably, for example, 0 to 80°C, more preferably 10 to 40°C, and more preferably room temperature. The reaction time is preferably, for example, 12 to 48 hours, more preferably 16 to 20 hours. The reaction can be carried out under an air atmosphere or an inert atmosphere such as nitrogen or argon, but is preferably carried out under an inert atmosphere such as nitrogen or argon. After completion of the reaction, the resulting solid is filtered, washed with a solvent, and then vacuum-dried to obtain the target compound represented by formula (1b-1). Examples of the solvent used for washing include the same solvents as those exemplified as reaction solvents.

[0061] In the second embodiment, the iron compound represented by the formula (1b-1) is reacted with the compound represented by the formula (1b-2) to produce the target iron complex compound.

[0062] R in the formula (1b-2) １ , R ２ , R ３ , and R ４ are R in formula (1B) of "1. Iron complex compound" above. １ , R ２ , R ３ , and R ４ The same preferred examples are also given.

[0063] In formula (1b-2), each M is independently an alkali metal, such as lithium, sodium, or potassium, and is preferably sodium or potassium.

[0064] The compound represented by formula (1b-2) can be the same as the compound represented by formula (1a-2), and can be easily obtained as a commercially available product or by a known synthesis method.

[0065] The reaction of the iron compound represented by formula (1b-1) with the compound represented by formula (1b-2) can be carried out in the presence or absence of a solvent, but is preferably carried out in the presence of a solvent since the reaction proceeds uniformly. The type of solvent is not particularly limited, and examples include the same solvents as those exemplified in the first embodiment. The solvent may be used alone or in combination of two or more. For example, when the compound represented by formula (1b-2) has a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, it is preferable to use tetrahydrofuran, diethyl ether, benzene, or toluene as the solvent. Furthermore, for example, when the compound represented by formula (1b-2) is a -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ In this case, it is preferable to use diethyl ether, benzene, or toluene as the solvent.

[0066] The reaction temperature of the iron compound represented by formula (1b-1) and the compound represented by formula (1b-2) is, for example, preferably 0 to 80°C, more preferably 20 to 80°C. The reaction time is, for example, preferably 1 to 48 hours, more preferably 4 to 20 hours. The reaction can be carried out under an air atmosphere or an inert atmosphere such as nitrogen or argon, but is preferably carried out under an inert atmosphere such as nitrogen or argon. After completion of the reaction, insoluble matter is removed by filtration, and the mixture is then vacuum dried to obtain the target compound represented by formula (1B). The obtained compound may be purified by a conventional method. For example, the obtained compound may be purified by dissolving the obtained compound in an appropriate solvent, filtering, and then vacuum drying or recrystallizing the filtrate. Examples of solvents used for the purification treatment include the same as those exemplified as the reaction solvent.

[0067] The compound represented by the formula (1B) may produce stereoisomers depending on the coordination mode or conformation of the ligand, and may be a mixture of these stereoisomers or a pure single isomer.

[0068] 3. Method for Producing Organosilicon Compounds A method for producing an organosilicon compound according to one aspect of the present invention comprises reacting alkenes with hydrosilanes in the presence of the iron complex compound described above. According to this aspect, the iron complex compound cleaves the silicon-hydrogen bonds of the hydrosilanes and catalyzes an addition reaction of the alkenes to carbon-carbon unsaturated bonds, thereby producing an organosilicon compound. In this specification, the term "organosilicon compound" refers to a compound containing one or more bonds between a silicon atom and a carbon atom.

[0069] The iron complex compound and its production method are as described above in "1. Iron Complex Compound" and "2. Production Method of Iron Complex Compound." The amount of the iron complex compound used is not particularly limited and can be appropriately selected depending on the purpose. The amount of the iron complex compound used is, for example, preferably 0.000001 equivalents or more, more preferably 0.00001 equivalents or more, and even more preferably 0.0001 equivalents or more, relative to 1 equivalent of the hydrosilane substrate. Also, the amount is preferably 0.1 equivalents or less, more preferably 0.01 equivalents or less, and even more preferably 0.001 equivalents or less. Alternatively, the amount is preferably 0.0001 mol% or more, more preferably 0.001 mol% or more, and even more preferably 0.01 mol% or more, relative to the hydrosilane substrate. Furthermore, the amount is preferably 10 mol% or less, more preferably 1 mol% or less, and even more preferably 0.1 mol% or less, relative to the hydrosilane substrate. Within the above range, a sufficient reaction rate can be obtained, purification is easy, and an organosilicon compound can be produced efficiently. The iron complex compounds may be used alone or in combination of two or more. When two or more types are used in combination, the total amount used is preferably within the above range.

[0070] In this embodiment, the alkene is not particularly limited as long as it is a compound having at least one carbon-carbon double bond in the molecule, and examples of the alkene include an olefin compound, a silane compound, and an organopolysiloxane compound, each of which has at least one carbon-carbon double bond in the molecule.

[0071] The hydrosilanes are not particularly limited as long as they have at least one Si—H bond in the molecule, and examples of the hydrosilanes include silane compounds and organopolysiloxane compounds having at least one Si—H bond in the molecule.

[0072] The structures of the alkenes and hydrosilanes are not particularly limited, and compounds having any structure can be used in any combination. The structure, molecular weight, etc. of the organosilicon compound obtained by the reaction of the alkenes and hydrosilanes are also not particularly limited.

[0073] Appropriate reaction temperature and reaction time can be appropriately selected by those skilled in the art depending on the types of alkenes and hydrosilanes, the combination thereof, the intended use, etc. The reaction can be carried out under an air atmosphere or an inert atmosphere such as nitrogen or argon, but is preferably carried out under an inert atmosphere such as nitrogen or argon.

[0074] The method for producing an organosilicon compound according to this embodiment can be used for all applications where conventional industrial production has been performed using platinum catalysts, such as the production of cured silicone materials, silane coupling agents, or modified silicone oils. The method for producing an organosilicon compound according to this embodiment is particularly suitable for use in the production of cured silicone materials. When at least one or both of the alkenes and hydrosilanes are organopolysiloxane compounds (silicones), the iron complex compound has high solubility in the organopolysiloxane compound, allowing the reaction to proceed more efficiently and uniformly, suppressing the occurrence of curing spots and enabling the production of high-quality cured silicone materials.

[0075] The present invention will be explained in more detail below by way of examples and comparative examples, but the present invention is not limited to these examples as long as it does not depart from the gist of the invention.

[0076] <Production of Iron Complex Compounds> Iron complex compounds having a tridentate ligand were produced according to the following reaction pathway. Iron Compound (1), Iron Compound (2), and Iron Compound (3) were produced by referring to the methods described in the following publications (Kamitani, M.; Kusaka, H.; Toriyabe, T.; Yuge, H., Bull. Chem. Soc. Jpn., 2018, 91, 1429-1435 (Non-Patent Document 3); Britovsek, GJP; Gibson, VC; McTavish, SJ; Solan, GA; White, AJP; Williams, DJ; Britovsek, GJP; Kimberley, BS; Maddox, PJ Chem. Commun. 1998, 849-850 (Non-Patent Document 4)).

[0077]

[0078] Example 1: Under a nitrogen atmosphere, a tetrahydrofuran (THF, 10 mL) solution containing iron compound (1) (200 mg, 0.428 mmol) and sodium stearate (262 mg, 0.856 mmol) was stirred at 60°C for 16 hours and then cooled to room temperature (25°C). After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was then dissolved in hexane (5 mL) and filtered. The filtrate was dried under vacuum to obtain the target iron complex compound (4) (239 mg, 0.244 mmol, yield: 57%).

[0079]

[0080] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ３８ H ５７ O ２ N ２ FPFe[M-C １７ H ３５ CO ２ ] ＋ Calculated value 679.3491; measured value 679.3493. １ H NMR (400 MHz, C６ D ６ ): δ 168.68, 158.10, 153.42, 137.96, 69.58, 63.83, 49.66, 47.07, 26.51, 25.64, 18.79, 17.96, 11.24, 9.64, 9.30, 4.28, 3.30, 1.27, 1.11, 0.91, 0.77, 0.49, 0.28, 0.16, -0.81, -12.81, -13.05. １９ F{ １ H} NMR (376 MHz, C ６ D ６ ): δ -10.77.

[0081] Example 2: Under an argon atmosphere, a THF (10 mL) solution containing iron compound (1) (200 mg, 0.428 mmol) and sodium oleate (261 mg, 0.856 mmol) was stirred at room temperature (25°C) for 16 hours. After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was then dissolved in hexane (5 mL) and filtered. The filtrate was dried under vacuum to obtain the target iron complex compound (5) (384 mg, 0.394 mmol, yield: 92%).

[0082]

[0083] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI) and nuclear magnetic resonance spectroscopy (NMR). ３８ H ５５ O ２ N ２ FPFe[M-C １７ H ３３ CO ２ ] ＋ Calculated value 677.3329; measured value 677.3330. １ H NMR (400 MHz, C ６ D ６ ): δ 137.00, 68.61, 62.54, 46.75, 28.13, 25.64, 17.85, 9.68, 5.38, 5.29, 4.20, 3.30, 1.95, 1.78, 0.56, 0.29, -0.59, -12.99.１９ F{ １ H} NMR (376 MHz, C ６ D ６ ): δ -11.53.

[0084] Example 3: Under an argon atmosphere, a THF (10 mL) solution containing iron compound (2) (229 mg, 0.428 mmol) and sodium oleate (261 mg, 0.856 mmol) was stirred at room temperature (25°C) for 16 hours. After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was then washed with hexane (2 mL, twice) and dried under vacuum to obtain the target iron complex compound (6) (201 mg, 0.193 mmol, yield: 45%).

[0085]

[0086] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI) and nuclear magnetic resonance spectroscopy (NMR). ４４ H ５１ O ２ N ２ FPFe[M-C １７ H ３３ CO ２ ] ＋ Calculated value 745.3016; measured value 745.3015. １ H NMR (400 MHz, C ６ D ６ ): δ 73.37, 64.38, 48.99, 24.30, 21.72, 19.38, 15.81, 8.58, 8.42, 8.40, 7.97, 7.52, 7.50, 6.93, 6.63, 6.58, 6.38, 5.47, 3.59, 2.09, 1.26, 1.11, 0.88, -5.08, -10.98. １９ F{ １ H} NMR (376 MHz, C ６ D ６ ): δ -10.86.

[0087] Example 4: Under an argon atmosphere, a THF (10 mL) solution containing iron compound (3) (212 mg, 0.428 mmol) and sodium oleate (261 mg, 0.856 mmol) was stirred at room temperature (25°C) for 16 hours. After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was then dissolved in hexane (5 mL) and filtered. The filtrate was dried under vacuum to obtain the target iron complex compound (7) (378 mg, 0.377 mmol, yield: 88%).

[0088]

[0089] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI) and nuclear magnetic resonance spectroscopy (NMR). ４３ H ６０ O ２ N ３ Fe[M-C １７ H ３３ CO ２ ] ＋ Calculated value 706.4029; measured value 706.4025. １ H NMR (400 MHz, C ６ D ６ ): δ 67.37, 40.27, 33.91, 31.36, 29.33, 27.71, 22.73, 14.57, 12.78, 11.24, 8.49, 7.96, 7.28, 7.06, 6.99 , 6.97, 6.50, 5.54, 4.52, 4.14, 3.70, 3.18, 3.07, 2.50, 2.16, 2.03, 1.88, 1.29, 0.89, -10.77, -15.73.

[0090] Example 5: Under an argon atmosphere, a diethyl ether (10 mL) solution containing iron complex compound (1) (253 mg, 0.542 mmol) and potassium trimethylsilanoxide (142 mg, 1.11 mmol) was stirred at room temperature (25°C) for 16 hours. After removing insoluble matter by filtration, the diethyl ether was distilled off under reduced pressure. The residue was then washed with hexane (1 mL, twice) and dried under vacuum to obtain the target iron complex compound (8) (63.9 mg, 0.108 mmol, yield: 20%).

[0091]

[0092] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ２３ H ３１ ON ２ FPSiFe[M-Me ３ SiO] ＋ Calculated value 485.1271; measured value @ 485.1262. １ H NMR (600 MHz, C ６ D ６ ): δ164.77, 70.10, 66.01, 44.60, 15.54, 9.22, 2.95, 1.45, 0.86, 0.04, -27.90. １９ F{ １ H} NMR (376 MHz, C ６ D ６ ): δ -14.65.

[0093] Example 6: Under an argon atmosphere, a diethyl ether (10 mL) solution containing iron complex compound (1) (200 mg, 0.428 mmol) and potassium hexamethyldisilazide (166 mg, 0.835 mmol) was stirred at room temperature (25°C) for 16 hours. After removing insoluble matter by filtration, the diethyl ether was distilled off under reduced pressure. The residue was then dissolved in hexane, filtered, and dried under vacuum to obtain the target iron complex compound (9) (216 mg, 0.283 mmol, yield: 66%).

[0094]

[0095] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ２６ H ４０ N ３ FPSi ２ Fe[M-(Me ３ Si) ２ N] ＋ Calculated value 556.1826; measured value 556.1823. １ H NMR (400 MHz, C ６ D６ ): δ 69.01, 60.35, 57.54, 53.52, 46.02, 38.69, 36.59, 22.58, 14.27, 13.56, 10.17, 0.10, -3.58, -4.02, -7.02, -9.25, -11.31, -15.90, -21.55. １９ F{ １ H} NMR (376 MHz, C ６ D ６ ): δ -24.64.

[0096] Example I: Under a nitrogen atmosphere, a tetrahydrofuran (THF, 10 mL) solution containing iron compound (1) (200 mg, 0.428 mmol) and sodium myrstate (213 mg, 0.852 mmol) was stirred at 60°C for 16 hours and then cooled to room temperature (25°C). After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was dried in vacuo to obtain the target iron complex compound (a) (246 mg, 0.289 mmol, yield: 68%).

[0097]

[0098] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ３４ H ４９ O ２ N ２ FPFe[M-C １３ H ２７ CO ２ ] ＋ Calculated value 623.2860; measured value 628.2856. 1 H NMR signals were broad. 1H NMR (600 MHz, C6D6): δ 168.29, 161.20, 152.15, 138.74, 70.02, 68.65, 49.94, 47.17, 26.50, 26.04, 25.67, 18.79, 18.58, 11.20, 8.75, 8.40, 8.13, 3.58, 2.48, 1.25, 0.98, 0.78, 0.50, 0.30, 0.15, -0.84, -13.87, -14.44. 19 F{ 1 H} NMR (564 MHz, C6D6): δ -10.38.

[0099] Example II: Under a nitrogen atmosphere, a tetrahydrofuran (THF, 10 mL) solution containing iron compound (1) (200 mg, 0.428 mmol) and sodium lignocerate (333 mg, 0.852 mmol) was stirred at 60°C for 16 hours and then cooled to room temperature (25°C). After removing insoluble matter by filtration, the THF was distilled off under reduced pressure. The residue was dried in vacuo to obtain the target iron complex compound (b) (269 mg, 0.238 mmol, yield: 55%).

[0100]

[0101] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ４４ H ６９ O ２ N ２ FPFe[M-C ２３ H ４７ CO ２ ] ＋ Calculated value 763.4425; measured value 763.4416. 1 H NMR (600 MHz, C6D6): δ 168.40, 159.03, 153.18, 138.95, 70.92, 70.06, 65.35, 64.00, 49.64, 47.59, 26.17, 25.51, 18.30, 17.05, 11.10, 8.56, 8.15, 6.33, 4.43, 3.37, 2.50, 1.26, 0.94, -13.75.19 F{ 1 H} NMR (564 MHz, C6D6): δ -10.05.

[0102] <Method for Producing Organosilicon Compounds> As shown below, various investigations were carried out in order to produce organosilicon compounds using the hydrosilylation reaction of alkenes.

[0103] [Examples 7 to 10] Under an argon atmosphere, iron complex compound (4), (5), (8), or (9) (10 μmol, each 0.1 mol% relative to phenylsilane) was added to a mixed solution of phenylsilane (1.32 mL, 10.7 mmol) and 1-octene (1.68 mL, 10.7 mmol). The reaction mixture was stirred at 25°C for 1 hour, and the product was １ This was confirmed by H NMR spectroscopy and GC-MS. In both cases, the silane and olefin were completely consumed, and the hydrosilylated product PhH ２ SiC ８ H １７ It was confirmed that PhH was produced in a 100% yield. The results are shown in Table 1. ２ SiC ８ H １７ of １ HNMR (600MHz, CDCl ３ ): δ 7.59-7.55 (m, 2H, Ph), 7.42-7.33 (m, 3H, Ph), 4.28 (t, J=3.7Hz, 2H, SiH ２ ), 1.50-1.42 (m, 2H, CH ２ ), 1.40-1.33 (m, 2H, CH ２ ), 1.33-1.21 (m, 6H, CH ２ ), 1.01-0.84 (m, 2H, CH ２ ), 0.91-0.83 (m, 5H, CH ２ and CH ３ ).

[0104]

[0105]

[0106] [Examples 11 to 24] Under an argon atmosphere, a mixture of iron complex compound (4), (7), (8), (9), (a), or (b), vinyl-terminated polydimethylsiloxane (A), and methylhydrosiloxane-dimethylsiloxane copolymer (B) was heated for 40 hours at the mixing ratios and reaction temperatures shown in Table 2, and the dissolution of the iron complex compound (uniformity of the mixture) and the progress of curing were confirmed. The iron complex compound having a long-chain alkyl or organosilyl structure produced by the present invention was shown to dissolve and disperse uniformly in the mixture of (A) and (B), thereby curing the silicone evenly after heating.

[0107]

[0108] Comparative Examples 1 and 2: Experiments were conducted under the same conditions as in Example 11, except that iron complex compound (10) or (11) lacking a long-chain alkyl or organosilyl structure was used. The iron complex compound did not dissolve uniformly, and curing did not proceed or curing spots occurred. Iron complex compounds (10) and (11) were produced by the methods described in Kamitani, M.; Kusaka, H.; Toriyabe, T.; Yuge, H., Bull. Chem. Soc. Jpn., 2018, 91, 1429-1435 (Non-Patent Document 3) and JP 2020-117474 A (Patent Document 1).

[0109]

[0110] Comparative Example 3: Under a nitrogen atmosphere, a tetrahydrofuran (THF, 10 mL) solution containing iron compound (1) (200 mg, 0.428 mmol) and sodium laurate (189 mg, 0.852 mmol) was stirred at 60°C for 16 hours and then cooled to room temperature (25°C). Insoluble matter was removed by filtration, and the THF was distilled off under reduced pressure. The residue was dried in vacuo to obtain the target iron complex compound (c) (292 mg, 0.367 mmol, yield: 86%).

[0111]

[0112] The resulting compound was analyzed by high-resolution mass spectrometry (HRMS / ESI method) and nuclear magnetic resonance spectroscopy (NMR). HRMS (ESI) measurement: C ３２ H ４５ O ２ N ２ FPFe[M-C １１ H ２３ CO ２ ] ＋ Calculated value 595.2547; measured value 595.2544. 1 H NMR (600 MHz, C6D6): δ 139.34, 70.18, 68.79, 62.95, 50.03, 47.21, 26.58, 25.75, 18.67, 18.22, 11.22, 9.67, 9.23, 8.75, 8.40, 8.09, 6.58, 2.48, 2.11, 1.78, -0.32, -0.63, -13.95, -14.51. 19 F{ 1 H} NMR (564 MHz, C6D6): δ -10.09.

[0113] An experiment was carried out under the same conditions as in Example 11 except that the iron complex compound (c) obtained above, which did not have a long-chain alkyl group, was used. As a result, the iron complex compound did not dissolve uniformly, and hardening spots occurred.

[0114] The results of Examples 11 to 24 and Comparative Examples 1 to 3 are shown in Table 2. In the table, the iron complex compound was rated "dissolved" when it was uniformly dissolved in the mixture, and "insoluble" when insoluble matter was visually observed but it was not uniformly dissolved. The progress of curing was evaluated visually to determine whether the mixture had fluidity. A cured mixture with no visible fluidity was rated "cured," while a fluid, liquid-like mixture was rated "uncured." The cured mixture was broken down to one-tenth of its original size using a metal rod or similar tool. A case in which no liquid was generated from the inside was rated "absent," and a case in which liquid was generated from the inside was rated "present." As shown in Table 2, the iron complex compound, having a hydrocarbon group with 13 or more carbon atoms or an organosilyl structure, allowed the complex compound to dissolve and uniformly disperse in the mixture of (A) and (B), and the silicone was cured without any curing spots after heating (Examples 11 to 24). On the other hand, when the number of carbon atoms in the hydrocarbon group was short, the complex compound did not dissolve in the mixed solution of (A) and (B), and curing did not proceed (Comparative Example 1), or even if cured, curing spots occurred (Comparative Examples 2 and 3).

[0115] The iron complex compound of the present invention can be suitably used as a hydrosilylation catalyst in the organosilicon industry, particularly in the production of cured silicone materials and organosilicon compounds. Because the iron complex compound of the present invention has high solubility in silicone, it is particularly useful in applications using silicone as a raw material, and can efficiently produce organosilicon compounds and cured silicone materials.

Claims

1. Formula (1): (L)FeA ｎ１ (1) wherein n1 is 2 or 3, and each A is independently -OR １ , -OC(=O)R ２ , or -NR ３ R ４ and R １ , R ２ , R ３ , and R ４ each independently represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ m is an integer of 0 to 11; １ and R １ is a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, R １ They are linked together to form a ring structure -O-C(R ａ ) may form —O—, R ａ represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent; L represents a group represented by formula (L-1): [In the formula, R ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R ７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer from 0 to 4, provided that R ５ is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ is bonded to a carbon atom of the quinoline skeleton.] or Formula (L-2): [In the formula, R ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１ may be linked to form a cyclic structure, R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer from 0 to 3, with the proviso that R ９ represents a tridentate ligand represented by the following formula: embedded image bonded to a carbon atom of a pyridine skeleton.

2. Formula (1A-1), (1A-2), or (1A-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ５ , R ６ , R ７ , R ８ , R ａ , n2, and n3 are as defined above.] The iron complex compound according to claim 1, 3. Formula (1B-1), (1B-2), or (1B-3): [In the formula, R １ , R ２ , R ３ , R ４ , R ９ , R １０ , R １１ , R １２ , R １３ , R ａ , and n4 are as defined above.] The iron complex compound according to claim 1, 4. Formula (1a-1): [In the formula, X １ and X ２ are each independently a halogen atom; R ５ and R ６ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R ７ and R ８ are each independently an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R ７ and R ８ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R ７ and R ８ may be linked to form a cyclic structure; n2 is an integer from 0 to 4, provided that R ５ is bonded to a carbon atom of the pyridine skeleton; n3 is an integer of 0 to 5, provided that R ６ is bonded to a carbon atom of the quinoline skeleton.] and an iron compound represented by the formula: R １ O.M., R. ２ COOM or NR ３ R ４ M (1a-2) [wherein, R １ , R ２ , R ３ , and R ４ each independently represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ wherein m is an integer of 0 to 11; and each M is independently an alkali metal.

5. Formula (1b-1): [In the formula, X １ and X ２ are each independently a halogen atom; R ９ are each independently an aliphatic hydrocarbon group having 1 to 6 carbon atoms which may have a substituent, an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, or a halogen atom; R １０ , R １１ , R １２ , and R １３ are each independently a hydrogen atom, an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, or an aromatic hydrocarbon group having 6 to 12 carbon atoms which may have a substituent, provided that R １０ and R １１ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １０ and R １１ may be linked to form a cyclic structure, R １２ and R １３ is an aliphatic hydrocarbon group having 1 to 12 carbon atoms which may have a substituent, R １２ and R １３ may be linked to form a cyclic structure; n4 is an integer from 0 to 3, with the proviso that R ９ is bonded to a carbon atom of the pyridine skeleton. １ O.M., R. ２ COOM or NR ３ R ４ M (1b-2) [wherein, R １ , R ２ , R ３ , and R ４ each independently represents a hydrocarbon group having 13 to 24 carbon atoms which may have a substituent, or -Si(CH ３ ) ２ -[OSi(CH ３ ) ２ ] ｍ -CH ３ wherein m is an integer of 0 to 11; and each M is independently an alkali metal.

6. A method for producing an organosilicon compound, which comprises reacting an alkene with a hydrosilane in the presence of the iron complex compound according to claim 1, 2 or 3.

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