Preparation method of alkenyl silane compound

Abstract

The invention relates to a preparation method of an alkenyl silane compound, which comprises the following steps: under a protective atmosphere, reacting a silazane compound, an olefin compound, a catalytic amount of titanium catalyst and a catalytic amount of tetrahydrofuran solution of phenyl magnesium bromide or methyl magnesium bromide at 100-120 DEG C for 12-24 hours, and then performing column chromatography purification to obtain the alkenyl silane compound. And the various different substituted alkenyl silane compounds are obtained. The method is simple to operate and low in cost, a series of alkenyl silicon compounds which are difficult to synthesize by a traditional method can be obtained, various compounds can be obtained through further functionalization, and the alkenyl silicon compounds are applied to development and research of medicines and organic functional materials.

Description

Technical Field

[0001] The invention relates to the technical field of organic synthesis, and in particular to a method for preparing alkenyl silane compounds. Background Art

[0002] Silicone is a rich and practical organic compound. As an important intermediate in synthetic chemistry, it is widely used in research fields such as materials science and the pharmaceutical industry. Silicone compounds have become compounds with extensive transformation and synthetic value due to their relative stability and wide reactivity. In recent years, as silicon-containing compounds are a very useful class of synthetic intermediates, their synthesis and application have attracted the attention of more and more chemists.

[0003] Organosilicon compounds play an important role in synthetic chemistry due to their abundance, stability and low toxicity. As one of the important organosilicon compounds, alkenyl silicon is also widely used in organic synthesis, material chemistry, life sciences and other fields. The usual methods for synthesizing alkenyl silane compounds include silylation of olefins, hydrosilylation of alkynes, and the reaction of Grignard reagents with alkenyl-substituted chlorosilanes. Although the above methods can be used to prepare alkenyl silanes, the compatibility of functional groups is limited, and there is still a lack of efficient synthesis methods. Summary of the invention

[0004] The technical problem to be solved by the present invention is to provide a method for preparing alkenyl silane compounds which is simple to operate and low in cost.

[0005] In order to solve the above problems, the present invention discloses a method for preparing alkenyl silane compounds, which is characterized in that: the method comprises reacting a silacyclobutane compound, an olefin compound, a catalytic amount of a titanium catalyst and a catalytic amount of a tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide at 100 to 120° C. under a protective atmosphere, and then performing column chromatography purification after reacting for 12 to 24 hours to obtain a plurality of differently substituted alkenyl silane compounds.

[0006] The reaction equation is:

[0007]

[0008] The molar ratio of the silacyclobutane compound to the olefin compound is 1:1-1:1.2 or 1.2:1.

[0009] The silacyclobutane compound is benzosilacyclobutane or silacyclobutane;

[0010] The benzosilacyclobutane has the following structural formula:

[0011]

[0012] The silacyclobutane has the following structural formula:

[0013]

[0014] Where: R 1 , R 2 is one of methyl and substituted phenyl; R 3 is a fluorine atom or a hydrogen atom; Aryl is an aryl group or an aromatic heterocycle.

[0015] The R 1 or R 2 is one of methyl, phenyl and 4-methylphenyl; Aryl is one of phenyl, 4-methylphenyl, 4-trifluoromethoxyphenyl, 4-tert-butylphenyl and thienyl.

[0016] The olefin compound is a substituted styrene or a substituted vinyl silane;

[0017] The substituted styrenes have the following structural formula:

[0018]

[0019] The substituted vinyl silanes have the following structural formula:

[0020]

[0021] Where: R 4 is methyl; R 5 is methyl or ethyl; R 6 It is methyl or phenyl.

[0022] The substituted styrenes are 4-methylstyrene, 4-methoxystyrene, 4-tert-butylstyrene, 4-phenylstyrene, 4-fluorostyrene, 4-phenoxystyrene, 4-N,N-dimethylstyrene, 4-trimethylsilylstyrene, 4-vinylstyrene, 3-methylstyrene, 3-methoxystyrene, 2-methylstyrene, 2-methoxystyrene, 2-fluorostyrene, 2-vinylnaphthalene, 3-vinylbicyclo[4.2.0]octa-1,3,5-triene, vinylferrocene, 3,4-dimethylstyrene, 3 , 4-dimethoxystyrene, 3,4,5-trimethoxystyrene, (2-(4-vinylphenyl)ethylene-1,1,2-triyl)triphenyl, 1,3,3-trimethyl-2-(4-vinylphenoxy)bicyclo[2.2.1]heptane, 1-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)-4-vinylbenzene; the substituted vinyl silane is one of trimethyl(vinyl)silane, dimethyl(phenyl)(vinyl)silane, and diethyl(methyl)(vinyl)silane.

[0023] The amount of the titanium catalyst used is 10 mol% of the amount of the silacyclobutane compound used.

[0024] The concentration of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 1.0 mol / L, and the amount of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 10-20 mol% of the amount of the silacyclobutane compound.

[0025] The eluent used for column chromatography purification is petroleum ether (PE), or a mixed solution of petroleum ether (PE) and ethyl acetate (EA) uniformly mixed in a volume ratio of 50:1 to 100:1.

[0026] The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

[0027] Compared with the prior art, the present invention has the following advantages:

[0028] 1. The catalyst in the present invention is a tetrahydrofuran solution of a titanium catalyst and phenylmagnesium bromide or methylmagnesium bromide. The catalyst is abundant in the earth's reserves and is cheap and easy to obtain, which greatly reduces the production cost.

[0029] 2. The present invention does not require the addition of expensive and difficult-to-synthesize ligands, and can achieve the silylation reaction of silacyclobutane compounds and olefin compounds with high chemical selectivity under relatively mild conditions, thereby obtaining a series of alkenyl silicon compounds that are difficult to synthesize by traditional methods. Therefore, it has certain guiding significance for enriching the synthesis methods of organosilicon compounds.

[0030] 3. The present invention is simple to operate, low in cost, applicable to a variety of substrates, and has a wide range of functional group applicability.

[0031] 4. The one-step synthesis method of the present invention has mild reaction conditions and a medium to high yield; the vinylsilane structure compound synthesized by this method can be further functionalized to obtain various compounds, which can be applied to the development and research of drugs and organic functional materials. DETAILED DESCRIPTION

[0032] A method for preparing alkenyl silane compounds, comprising reacting silacyclobutane compounds, olefin compounds, a catalytic amount of a titanium catalyst and a catalytic amount of a tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide at 100-120° C. under a protective atmosphere, wherein the amount of the titanium catalyst is 10 mol% of the amount of the silacyclobutane compounds, the concentration of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 1.0 mol / L, and the amount of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 10-20 mol% of the amount of the silacyclobutane compounds. After reacting for 12-24 hours, column chromatography purification is performed to obtain a plurality of differently substituted alkenyl silane compounds.

[0033] Wherein: the molar ratio of the silacyclobutane compound to the olefin compound is 1:1-1:1.2 or 1.2:1.

[0034] The silacyclobutane compound is benzosilacyclobutane or silacyclobutane;

[0035] Benzosilacyclobutane has the following structural formula:

[0036]

[0037] Silicacyclobutane has the following structural formula:

[0038]

[0039] Where: R 1 , R 2 is one of methyl and substituted phenyl; R 3 is a fluorine atom or a hydrogen atom; Aryl is an aryl group or an aromatic heterocycle. 1 or R 2 is one of methyl, phenyl and 4-methylphenyl; Aryl is one of phenyl, 4-methylphenyl, 4-trifluoromethoxyphenyl, 4-tert-butylphenyl and thienyl.

[0040] The olefin compound is a substituted styrene or a substituted vinyl silane;

[0041] Substituted styrenes have the following structural formula:

[0042]

[0043] The substituted styrenes are preferably one of 4-methylstyrene, 4-methoxystyrene, 4-tert-butylstyrene, 4-phenylstyrene, 4-fluorostyrene, 4-phenoxystyrene, 4-N,N-dimethylstyrene, 4-trimethylsilylstyrene, 4-vinylstyrene, 3-methylstyrene, 3-methoxystyrene, 2-methylstyrene, 2-methoxystyrene, 2-fluorostyrene, 2-vinylnaphthalene, 3-vinylbicyclo[4.2.0]octa-1,3,5-triene, vinylferrocene, 3,4-dimethylstyrene, 3,4-dimethoxystyrene, 3,4,5-trimethoxystyrene, (2-(4-vinylphenyl)ethylene-1,1,2-triyl)triphenyl, 1,3,3-trimethyl-2-(4-vinylphenoxy)bicyclo[2.2.1]heptane, and 1-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)-4-vinylbenzene.

[0044] Substituted vinyl silanes have the following structural formula:

[0045]

[0046] Where: R 4 is methyl; R 5 is methyl or ethyl; R 6 It is methyl or phenyl.

[0047] The substituted vinyl silane is preferably one of trimethyl(vinyl)silane, dimethyl(phenyl)(vinyl)silane and diethyl(methyl)(vinyl)silane.

[0048] The eluent used for column chromatography purification is petroleum ether (PE), or a mixed solution of petroleum ether (PE) and ethyl acetate (EA) in a volume ratio (ml / ml) of 50:1 to 100:1.

[0049] In the present invention, the mixing is preferably performed by mixing the silacyclobutane compound, the olefin compound, the titanium catalyst and a tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide in a pressure tube.

[0050] The method of adding the same in the present invention is not particularly limited and can be done by methods well known to those skilled in the art.

[0051] In the present invention, the reaction is carried out in a protective atmosphere, wherein the protective atmosphere is preferably a nitrogen atmosphere or an argon atmosphere; the pressure of the protective atmosphere is preferably 1 atm.

[0052] In the present invention, the reaction is preferably carried out under stirring conditions, and there is no particular limitation on the stirring conditions, and the reaction can be carried out using a process well known to those skilled in the art.

[0053] The present invention also preferably includes separation. Due to the low polarity of the finally obtained differently substituted alkenyl silanes, column chromatography with a low polarity eluent is required for separation. Other separation processes are not particularly limited and can be carried out by column chromatography and vacuum spin drying, which are well known to those skilled in the art.

[0054] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0055] Example 1

[0056] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), styrene (denoted as 2a, 0.2mmol, 20.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3a, and the separation yield was 79%.

[0057] The chemical reaction formula of the above preparation process is:

[0058]

[0059] The characterization data are:

[0060] 1 H NMR (400 MHz, deuterated chloroform) δ 7.48–7.43 (m, 2H), 7.43–7.39 (m, 1H), 7.38–7.33 (m, 2H), 7.29–7.19 (m, 6H), 7.16–7.12 (m, 1H), 7.10–7.05 (m, 2H), 6.86 (d, J = 19.1 Hz, 1H), 6.73 (d, J = 19.1 Hz, 1H), 2.23 (s, 3H), 0.65 (s, 3H).

[0061] 13 C NMR (101MHz, Chloroform-d) δ146.8,144.5,138.2,137.2,136.4,134.8,130.1,130.0,129.3,128.7,128.5,128.1,126.7,125.6,125.1,23.6,-2.6.

[0062] HRMS(ESI)m / z:[M+Na] + Calculate for C 22 H 22 NaSi + :337.1383; found:337.1386.

[0063] Example 2

[0064] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-methylstyrene (denoted as 2b, 0.2mmol, 23.6mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a compound of formula 3b with a separation yield of 78%.

[0065] The chemical reaction formula of the above preparation process is:

[0066]

[0067] The characterization data are:

[0068] 1 H NMR(400MHz,Chloroform-d)δ7.60–7.56(m,2H),7.55–7.52(m,1H),7.43–7.37(m,6H),7.36 -7.32(m,1H),7.25–7.15(m,3H),6.93(d,J=19.1Hz,1H),6.78(d,J=19.1Hz,1H),2.38(s,3H),2.36(s,3H),0.78(s,3H).

[0069] 13 C NMR(101MHz,Chloroform-d)δ146.7,144.6,138.4,137.3,136.4,135.6,135.0,1 34.9,130.1,129.9,129.4,129.3,128.0,126.7,125.1,124.1,23.6,21.4,-2.6.

[0070] HRMS(ESI)m / z:[M+H] + Calculate for C 23 H 25 Si + :329.1720,found:329.1730.

[0071] Example 3

[0072] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-tert-butylstyrene (denoted as 2c, 0.2mmol, 32.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3c. The separation yield was 89%.

[0073] The chemical reaction formula of the above preparation process is:

[0074]

[0075] The characterization data are:

[0076] 1 H NMR(400MHz,Chloroform-d)δ7.61-7.56(m,2H),7.56–7.52(m,1H),7.48–7.44(m,2H),7.44–7.38(m,5H),7.37–7.3 4(m,1H),7.24–7.19(m,2H),6.98(d,J=19.1Hz,1H),6.82(d,J=19.1Hz,1H),2.37(s,3H),1.36(s,9H),0.79(s,3H).

[0077] 13 C NMR(101MHz,Chloroform-d)δ151.7,146.6,144.6,137.3,136.5,135.6,135.0,134 .9,130.1,129.9,129.3,128.0,126.5,125.6,125.1,124.5,34.8,31.4,23.6,-2.6.

[0078] HRMS(ESI)m / z:[M+Na] + Calculate for C 26 H 30 NaSi + :393.2009; found:393.2042.

[0079] Example 4

[0080] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-phenylstyrene (denoted as 2d, 0.2mmol, 36.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3d, and the separation yield was 69%.

[0081] The chemical reaction formula of the above preparation process is:

[0082]

[0083] The characterization data are:

[0084] 1 H NMR(400MHz,Chloroform-d)δ7.59–7.48(m,9H),7.43–7.28(m,7H),7.20–7.14( m,2H),6.97(d,J=19.1Hz,1H),6.84(d,J=19.1Hz,1H),2.32(s,3H),0.74(s,3H).

[0085] 13 C NMR(101MHz,Chloroform-d)δ146.3,144.6,141.2,140.7,137.2,137.2,136.4,134.8,1 30.1,130.0,129.4,128.9,128.1,127.5,127.4,127.2,127.1,125.7,125.1,23.6,-2.6.

[0086] HRMS(APCI)m / z:[M+H] + Calculate for C 28 H 27 Si + :391.1877; found:391.1865.

[0087] Example 5

[0088] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-methoxystyrene (denoted as 2e, 0.2mmol, 26.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as eluent, the solvent was decompressed and dried to obtain a compound of formula 3e with a separation yield of 81%.

[0089] The chemical reaction formula of the above preparation process is:

[0090]

[0091] The characterization data are:

[0092] 1 H NMR(400MHz,Chloroform-d)δ7.58(dd,J=7.5,1.9Hz,2H),7.54(dd,J=7.6,1.6Hz,1H),7.48–7.40(m,2H),7.43–7 .32(m,4H),7.26–7.17(m,2H),6.97–6.87(m,3H),6.68(d,J=19.1Hz,1H),3.84(s,3H),2.36(s,3H),0.77(s,3H).

[0093] 13 C NMR(101MHz,Chloroform-d)δ159.9,146.2,144.6,137.5,136.4,135.1,134. 8,131.3,130.1,130.0,129.3,128.0,125.1,122.6,114.0,55.4,23.6,-2.6.

[0094] HRMS(ESI)m / z:[M+Na] + Calculate for C 23 H 24 OSi + :367.1489,found:367.1486

[0095] Example 6

[0096] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-phenoxystyrene (denoted as 2f, 0.2mmol, 39.2mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3f, and the separation yield was 71%.

[0097] The chemical reaction formula of the above preparation process is:

[0098]

[0099] The characterization data are:

[0100] 1 H NMR(400MHz,Chloroform-d)δ7.61–7.54(m,2H),7.57–7.50(m,1H),7.49–7.43(m,2H),7.43–7.35(m,3H),7.39–7.31(m,3H),7.26–7.17( m,2H),7.17–7.09(m,1H),7.08–7.01(m,2H),7.03–6.96(m,2H),6.94(d,J=19.1Hz,1H),6.74(d,J=19.1Hz,1H),2.35(s,3H),0.77(s,3H).

[0101] 13 C NMR(101MHz,Chloroform-d)δ157.6,157.1,145.9,144.5,137.2,136.4,134.9,134.8,133. 5,130.1,130.0,129.9,129.3,128.2,128.1,125.1,124.3,123.6,119.1,118.9,23.6,-2.6.

[0102] HRMS(ESI)m / z:[M+H] + Calculate for C 28 H 27 OSi + :407.1826; found:407.1832.

[0103] Example 7

[0104] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-tert-butylstyrene (denoted as 2g, 0.2mmol, 29.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (80:1) as the eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 3g, and the separation yield was 65%.

[0105] The chemical reaction formula of the above preparation process is:

[0106]

[0107] The characterization data are:

[0108] 1 H NMR(400MHz,Chloroform-d)δ7.57-7.55(m,2H),7.54–7.51(m,1H),7.41–7.35(m,5H),7.35–7.30(m,1H),7.19(m, 2H),6.88(d,J=19.0Hz,1H),6.70(d,J=8.8Hz,2H),6.54(d,J=19.0Hz,1H),2.98(s,6H),2.34(s,3H),0.74(s,3H).

[0109] 13 C NMR(101MHz,Chloroform-d)δ150.7,146.8,144.6,137.9,136.5,135.5,134.9,1 33.9,130.0,129.8,129.1,128.0,127.9,125.0,119.4,112.3,40.6,23.6,-2.5.

[0110] HRMS(ESI)m / z:[M+H] + Calculate for C 24 H 28 NSi + :358.1986,found:358.1982.

[0111] Example 8

[0112] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-trimethylsilylstyrene (denoted as 2h, 0.2mmol, 35.3mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3h. The separation yield was 71%.

[0113] The chemical reaction formula of the above preparation process is:

[0114]

[0115] The characterization data are:

[0116] 1 H NMR(400MHz,Chloroform-d)δ7.60-7.55(m,2H),7.55–7.50(m,3H),7.48–7.46(d,J=8.0Hz,2H),7.42-7.33(m,4H),7.24 -7.18(m,2H),6.98(d,J=19.1Hz,1H),6.88(d,J=19.1Hz,1H),2.36(s,3H),0.79(s,3H),0.28(s,9H).

[0117] 13 C NMR(101MHz,Chloroform-d)δ146.8,144.6,141.0,138.6,137.2,136.4,134. 9,133.7,130.1,130.0,129.3,128.1,126.0,126.0,125.1,23.6,-1.0,-2.6.

[0118] HRMS(ESI)m / z:[M+H] + Calculate for C 25 H 31 Si2 + :387.1959; found:387.1966.

[0119] Example 9

[0120] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-fluorostyrene (denoted as 2i, 0.2mmol, 22.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3i, and the separation yield was 47%.

[0121] The chemical reaction formula of the above preparation process is:

[0122]

[0123] The characterization data are:

[0124] 1 H NMR(400MHz,Chloroform-d)δ7.58–7.54(m,2H),7.52–7.50(m,1H),7.47–7.42(m,2H),7.42–7.36(m,3H),7.35–7.33( m,1H),7.23–7.18(m,2H),7.06–7.00(m,2H),6.91(d,J=19.1Hz,1H),6.73(d,J=19.1Hz,1H),2.33(s,3H),0.76(s,3H).

[0125] 1 3 C NMR(101MHz,Chloroform-d)δ160.5(d,J=250.1Hz).144.6,138.6(d,J=4.5Hz),137.0,136.4,134.8,130.1,130.0,1 29.7,129.7,129.4,128.8(d,J=3.8Hz),128.1,127.2(d,J=3.5Hz),125.2,124.2(d,J=3.5Hz),115.8,23.6,-2.8.19F NMR(376MHz,Chloroform-d)δ-113.46.

[0126] HRMS(ESI)m / z:[M+H] + Calculate for C 22 H 22 F + :333.1469; found:333.1461.

[0127] Example 10

[0128] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 3-methylstyrene (denoted as 2j, 0.2mmol, 22.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3j. The separation yield was 77%.

[0129] The chemical reaction formula of the above preparation process is:

[0130]

[0131] The characterization data are:

[0132] 1 H NMR(400MHz,Chloroform-d)δ7.61–7.52(m,3H),7.46–7.27(m,7H),7.22(m,2H),7.12(d,J=7.4 Hz,1H),6.96(d,J=19.1Hz,1H),6.84(d,J=19.1Hz,1H),2.38(s,3H),2.37(s,3H),0.78(s,3H).

[0133] 13 C NMR(101MHz,Chloroform-d)δ147.0,144.6,138.3,137.3,136.4,134.9,130.1,1 29.9,129.3,129.3,128.6,128.1,127.4,125.3,125.1,124.0,23.6,21.5,-2.6.

[0134] HRMS(ESI)m / z:[M+H] + Calculate for C 23 H 25 Si + :329.1720; found:329.1720.

[0135] Embodiment 11

[0136] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 3-methoxystyrene (denoted as 2k, 0.2mmol, 26.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3k. The separation yield was 77%.

[0137] The chemical reaction formula of the above preparation process is:

[0138]

[0139] The characterization data are:

[0140] 1 H NMR(400MHz,Chloroform-d)δ7.57–7.49(m,3H),7.41–7.30(m,4H),7.25–7.16(m,3H),7.06(m,1H ),7.00(m,1H),6.92(d,J=19.0Hz,1H),6.86–6.77(m,2H),3.81(s,3H),2.33(s,3H),0.75(s,3H).

[0141] 13 C NMR(101MHz,Chloroform-d)δ160.0,146.7,144.6,139.8,137.1,136.4,134.9,134.8,13 0.1,129.98,129.66,129.4,128.1,126.0,125.1,119.5,114.3,111.7,55.4,23.6,-2.6.

[0142] HRMS(ESI)m / z:[M+Na] + Calculate for C 23 H 24 NeA + :367.1489; found:367.1475.

[0143] Example 12

[0144] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 2-methylstyrene (denoted as 2l, 0.2mmol, 23.6mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 3l, and the separation yield was 73%.

[0145] The chemical reaction formula of the above preparation process is:

[0146]

[0147] The characterization data are:

[0148] 1 H NMR(400MHz,Chloroform-d)δ7.64–7.57(m,3H),7.57–7.53(m,1H),7.40(m,3H),7.38–7.32(m,1),7.26(m ,1H),7.25–7.18(m,4H),7.17–7.16(m,1H),6.74(d,J=18.9Hz,1H),2.37(s,3H),2.32(s,3H),0.79(s,3H).

[0149] 13 C NMR(101MHz,Chloroform-d)δ144.9,144.5,137.7,137.3,136.4,135.7,135.0,134.9,1 30.5,130.1,130.0,129.3,128.2,128.0,127.4,126.3,125.6,125.1,23.6,19.7,-2.6.

[0150] HRMS(APCI)m / z:[M+H] + Calculate for C 23 H 25 Si + :329.1720; found:329.1723.

[0151] Example 13

[0152] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 2-methoxystyrene (denoted as 2m, 0.2mmol, 26.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as the eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 3m. The separation yield was 68%.

[0153] The chemical reaction formula of the above preparation process is:

[0154]

[0155] The characterization data are:

[0156] 1 H NMR(400MHz,Chloroform-d)δ7.51–7.39(m,4H),7.28–7.23(m,3H),7.22–7.18(m,1H),7.17–7.09(m,2H),7.09–7. 03(m,2H),6.86–6.80(m,1H),6.75(d,J=7.2Hz,1H),6.67(d,J=19.3Hz,1H),3.70(s,3H),2.22(s,3H),0.65(s,3H).

[0157] 13 C NMR(101MHz,Chloroform-d)δ157.0,144.6,141.3,137.7,136.4,135.3,134.9,130.0,1 29.8,129.5,129.2,128.0,127.6,126.7,125.9,125.1,120.7,111.2,55.6,23.6,-2.7.

[0158] HRMS(APCI)m / z:[M+H] + Calculate for C 23 H 25 OSi + :345.1669; found:345.1673.

[0159] Embodiment 14

[0160] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 2-fluorostyrene (denoted as 2n, 0.2mmol, 24.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3n, and the separation yield was 43%.

[0161] The chemical reaction formula of the above preparation process is:

[0162]

[0163] The characterization data are:

[0164] 1 H NMR(400MHz,Chloroform-d)δ7.71(dd,J=7.7,1.8Hz,1H),7.68–7.63(m,2H),7.61(dd,J=7.7,1.6Hz,1H),7.52–7.41(m,4H ),7.37–7.27(m,4H),7.22(t,J=7.6Hz,1H),7.13(dd,J=10.1,8.8Hz,1H),7.00(d,J=19.3Hz,1H),2.44(s,3H),0.87(s,3H).

[0165] 13 C NMR (101MHz, Chloroform-d) δ161.7, 159.2, 144.5, 138.6 (d, J = 4.4Hz), 137.0, 136.4, 134.8, 134.7, 130.1 (d, J = 11.0Hz), 129.7 (d, J = 8.5Hz) ,129.4,128.8(d,J=3.6Hz),128.1,127.2(d,J=3.5Hz),126.2(d,J=11.7Hz),125.2,124.2(d,J=3.5Hz),115.9(d,J=22.2Hz),23.6,-2.8.19F NMR(376MHz,Chloroform-d)δ-118.99.

[0166] HRMS(ESI)m / z:[M+Na] + Calculate for C 22 H 21 FNaSi +:355.1289; found:355.1287.

[0167] Embodiment 15

[0168] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 2-vinylnaphthalene (denoted as 2o, 0.2mmol, 30.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3o with an isolation yield of 58%.

[0169] The chemical reaction formula of the above preparation process is:

[0170]

[0171] The characterization data are:

[0172] 1 H NMR(400MHz,Chloroform-d)δ7.81(m,4H),7.74(m,1H),7.62–7.58(m,2H),7.56(m,1H),7.51–7.43(m,2H) ,7.43–7.33(m,4H),7.22(m,2H),7.13(d,J=19.0Hz,1H),6.96(d,J=19.0Hz,1H),2.37(s,3H),0.80(s,3H).

[0173] 13 C NMR(101MHz,Chloroform-d)δ146.8,144.6,137.2,136.5,135.7,134.9,133.7,133.6,130.1,1 30.0,129.4,128.4,128.3,128.1,127.8,127.2,126.4,126.3,126.0,125.2,123.5,23.6,-2.6.

[0174] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H25Si + :365.1720; found:365.1730.

[0175] Example 16

[0176] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2 mmol, 42.0 mg), 3-vinylbicyclo[4.2.0]octa-1,3,5-triene (denoted as 2p, 0.2 mmol, 26.4 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M in THF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 100° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3p. The separation yield was 67%.

[0177] The chemical reaction formula of the above preparation process is:

[0178]

[0179] The characterization data are:

[0180] 1 H NMR(400MHz,Chloroform-d)δ7.43(ddd,J=15.7,7.4,1.6Hz,3H),7.29–7.18(m,4H),7.18–7.11(m,2H),7.10–7.03( m,2H),6.90(d,J=6.6Hz,1H),6.83(d,J=19.1Hz,1H),6.63(d,J=19.0Hz,1H),3.05(s,4H),2.23(s,3H),0.64(s,3H).

[0181] 13 C NMR(101MHz,Chloroform-d)δ147.9,146.5,146.2,144.5,137.4,137.3,136.4,135.1, 134.8,130.1,129.9,128.0,126.4,125.1,123.7,122.7,120.2,29.6,29.4,23.5,-2.6.

[0182] HRMS(APCI)m / z:[M+H] + Calculate for C 24 H 25 Si + :341.1720; found:341.1731.

[0183] Embodiment 17

[0184] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), vinylferrocene (denoted as 2q, 0.2mmol, 42.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3q, and the separation yield was 43%.

[0185] The chemical reaction formula of the above preparation process is:

[0186]

[0187] The characterization data are:

[0188] 1 H NMR(400MHz,Chloroform-d)δ7.60–7.48(m,3H),7.43–7.32(m,4H),7.22(d,J=7.3Hz,2H),6.74(d,J=18.9Hz,1 H),6.36(d,J=18.9Hz,1H),4.44(t,J=1.9Hz,2H),4.27(t,J=1.9Hz,2H),4.12(s,5H),2.38(s,3H),0.72(s,3H).

[0189] 13 C NMR(101MHz,Chloroform-d)δ145.7,144.5,137.6,136.4,135.4,134.9,130.1,129.8,129.2,128.0,125.0,122.1,84.4,69.4,69.3,67.1,23.6,-2.4.

[0190] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H 27 FeSi + :423.1220; found:423.1217.

[0191] Embodiment 18

[0192] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2 mmol, 42.0 mg), 1,3,3-trimethyl-2-(4-vinylphenoxy)bicyclo[2.2.1]heptane (denoted as 2r, 0.2 mmol, 51.9 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M in THF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 100° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as an eluent, the solvent was decompressed and dried to obtain a compound of formula 3r with a separation yield of 52%.

[0193] The chemical reaction formula of the above preparation process is:

[0194]

[0195] The characterization data are:

[0196] 1 H NMR(400MHz,Chloroform-d)δ7.60–7.46(m,3H),7.42–7.25(m,6H),7.21–7.13(m,2H),6.95–6.82(m,3H),6.61(d,J=16.7Hz,1H),3.87(s,1H) ,2.32(s,3H),2.09–1.94(m,1H),1.82–1.70(m,2H),1.64–1.53(m,1H), 1.53–1.40(m,1H),1.16(s,4H),1.08(s,4H),0.85(s,3H),0.72(s,3H).

[0197] 13 C NMR(101MHz,Chloroform-d)δ160.7,146.3,144.5,137.5,136.4,135.2,134.9,130.7,130.0,129.9,129.2 ,128.0,127.9,125.1,122.1,115.8,90.1,49.7,49.2,41.5,40.2,30.6,26.5,26.0,23.6,20.5,20.0,-2.5.

[0198] HRMS(ESI)m / z:[M+H] + Calculate for C 32 H 39 OSi + :467.2765; found:467.2771.

[0199] Embodiment 19

[0200] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2 mmol, 42.0 mg), 1-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)-4-vinylbenzene (denoted as 2s, 0.2 mmol, 56.1 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M in THF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 100° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as an eluent, the solvent was decompressed and dried to obtain a compound of formula 3s with a separation yield of 51%.

[0201] The chemical reaction formula of the above preparation process is:

[0202]

[0203] The characterization data are:

[0204] 1 H NMR(400MHz,Chloroform-d)δ7.59–7.48(m,3H),7.48–7.27(m,6H),7.23–7.05(m,2H ),6.90(d,J=10.3Hz,2H),6.86(s,1H),6.63(d,J=19.0Hz,1H),4.05(td,J=10.5,4.1H z,1H),2.34(s,3H),2.25–2.12(m,2H),1.73(d,J=14.3Hz,2H),1.50(d,J=10.1Hz,2H ),1.19–0.98(m,3H),0.93(dd,J=6.8,2.0Hz,6H),0.77(d,J=6.9Hz,3H),0.74(s,3H).

[0205] 13 C NMR(101MHz,Chloroform-d)δ158.7,146.2,144.5,137.4,136.3,135.1,134.8,130.9,130.0,129.8,129.1 ,128.0,127.9,125.0,122.1,115.7,77.6,48.0,40.3,34.5,31.5,26.1,23.7,23.5,22.2,20.8,16.6,-2.7.

[0206] HRMS(ESI)m / z:[M+H] + Calculate for C 32 H 41 OSi + :469.2921; found:469.2938.

[0207] Embodiment 20

[0208] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 4-vinylstyrene (denoted as 2t, 0.2mmol, 26.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3t, and the separation yield was 38%.

[0209] The chemical reaction formula of the above preparation process is:

[0210]

[0211] The characterization data are:

[0212] 1 H NMR(400MHz,Chloroform-d)δ7.56(d,J=9.2Hz,2H),7.51(s,1H),7.44(d,J=8.2Hz,2H),7.41–7.31(m,6H),7.24–7.16(m,2H),6.94(d,J=19 .1Hz,1H),6.82(d,J=18.0Hz,1H),6.72(dd,J=17.6,10.9Hz,1H),5.77(d,J=17.6Hz,1H),5.26(d,J=10.9Hz,1H),2.34(s,3H),0.76(s,3H).

[0213] 13 C NMR(101MHz,Chloroform-d)δ146.4,144.6,137.8,137.7,137.2,136.6,136.4,134. 9,134.9,130.1,130.0,129.4,128.1,127.0,126.6,125.6,125.1,114.2,23.6,-2.6.

[0214] Embodiment 21

[0215] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), (2-(4-vinylphenyl)ethylene-1,1,2-triyl)triphenyl (denoted as 2u, 0.2mmol, 71.7mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3u, and the separation yield was 37%.

[0216] The chemical reaction formula of the above preparation process is:

[0217]

[0218] The characterization data are:

[0219] 1 H NMR(400MHz,Chloroform-d)δ7.51(m,3H),7.42–7.30(m,4H),7.23–7.15(m,4H),7.11(m,9H) ,7.08–6.97(m,8H),6.85(d,J=19.0Hz,1H),6.73(d,J=19.0Hz,1H),2.31(s,3H),0.72(s,3H).

[0220] 13 C NMR(101MHz,Chloroform-d)δ146.6,144.5,144.1,143.8,143.8,143.8,141.3,140.7,137.3,136.4,136.2,134.9,134.8,1 31.7,131.5,131.5,130.1,129.9,129.3,128.0,127.9,127.8,127.8,126.7,126.6,126.6,126.1,125.1,125.1,23.6,-2.6.

[0221] HRMS(ESI)m / z:[M+H] + Calculate for C 42 H 37 Si + :569.2659; found:569.2648.)

[0222] Embodiment 22

[0223] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 3,4-dimethylstyrene (denoted as 2v, 0.2mmol, 26.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3v, and the separation yield was 67%.

[0224] The chemical reaction formula of the above preparation process is:

[0225]

[0226] The characterization data are:

[0227] 1 H NMR(400MHz,Chloroform-d)δ7.60–7.51(m,3H),7.44–7.32(m,4H),7.29(s,1H),7.27–7.17(m,3H),7.13 (d,J=7.8Hz,1H),6.93(d,J=19.1Hz,1H),6.77(d,J=19.1Hz,1H),2.36(s,3H),2.29(s,6H),0.77(s,3H).

[0228] 13 C NMR(101MHz,Chloroform-d)δ146.9,144.6,137.4,137.1,136.8,136.4,136.0,135.1,134 .9,130.1,130.0,129.9,129.3,128.0,128.0,125.1,124.3,123.9,23.6,19.9,19.8,-2.6.

[0229] HRMS(ESI)m / z:[M+H] + Calculate for C 24 H 27 Si + :343.1877; found:343.1874.

[0230] Embodiment 23

[0231] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), 3,4-dimethoxystyrene (denoted as 2w, 0.2mmol, 32.8mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (50:1) as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3w, and the separation yield was 58%.

[0232] The chemical reaction formula of the above preparation process is:

[0233]

[0234] The characterization data are:

[0235] 1 H NMR(400MHz,Chloroform-d)δ7.57(dd,J=7.4,1.9Hz,2H),7.55–7.51(m,1H),7.43–7.33(m,4H),7.21(dt,J=7.5,3.2Hz,2H),7.07–6. 99(m,2H),6.89(d,J=19.0Hz,1H),6.85(d,J=8.3Hz,1H),6.65(d,J=19.0Hz,1H),3.93(s,3H),3.91(s,3H),2.35(s,3H),0.77(s,3H).

[0236] 13 C NMR(101MHz,Chloroform-d)δ149.5,149.1,146.4,144.6,137.3,136.4,135.0,134.9,131 .5,130.1,129.9,129.3,128.0,125.1,122.8,120.2,111.0,108.7,56.1,56.0,23.6,-2.5.

[0237] HRMS(ESI)m / z:[M+Na] + Calculate for C 24 H 26 NaO2Si + :397.1594; found:397.1604.

[0238] Embodiment 24

[0239] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2 mmol, 42.0 mg), 3,4,5-trimethoxystyrene (denoted as 2x, 0.2 mmol, 38.8 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M inTHF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnet, and stirred at 100°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (50:1) as the eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3x with an isolation yield of 66%.

[0240] The chemical reaction formula of the above preparation process is:

[0241]

[0242] The characterization data are:

[0243] 1 H NMR(400MHz,Chloroform-d)δ7.62–7.54(m,2H),7.51(dd,J=7.8,1.6Hz,1H),7.45–7.31(m,4H),7.21(d,J= 7.3Hz,2H),6.86(d,J=19.0Hz,1H),6.80–6.66(m,3H),3.89(s,6H),3.86(s,3H),2.35(s,3H),0.76(s,3H).

[0244] 13 C NMR(101MHz,Chloroform-d)δ153.5,146.6,144.6,138.5,137.1,136.5,134.9,134 .8,134.0,130.1,130.0,129.4,128.1,125.1,124.8,103.7,61.1,56.2,23.6,-2.5.

[0245] HRMS(ESI)m / z:[M+Na] + Calculate for C 25 H 28 NaO3Si + :427.1700; found:427.1705.

[0246] Embodiment 25

[0247] In a glove box filled with nitrogen, 3-fluoro-substituted benzosilacyclosilabutane (denoted as 1b, 0.2mmol, 45.7mg), 4-tert-butylstyrene (denoted as 2c, 0.2mmol, 32.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3y with an isolation yield of 36%.

[0248] The chemical reaction formula of the above preparation process is:

[0249]

[0250] The characterization data are:

[0251] 1 H NMR(400MHz,Chloroform-d)δ7.57(dd,J=7.6,1.8Hz,2H),7.52–7.36(m,8H),7.00–6.94( m,1H),6.94–6.87(m,2H),6.78(d,J=19.0Hz,1H),2.35(s,3H),1.36(s,9H),0.77(s,3H).

[0252] 13 C NMR (101MHz, Chloroform-d) δ 165.5, 163.0, 151.8, 147.4 (d, J = 7.3Hz), 146.9, 138.3 (d, J = 7.9Hz), 137.1, 135. 5,134.8,129.4,128.1,126.5,125.7,124.1,117.1(d,J=19.6Hz),112.0(d,J=19.1Hz),34.8,31.4,23.5,-2.5.

[0253] 19 F NMR(376MHz,Chloroform-d)δ-112.23.

[0254] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H 30 F + :389.2095; found:389.2099.

[0255] Embodiment 26

[0256] In a glove box filled with nitrogen, silanol (denoted as 1c, 0.2mmol, 44.8mg) with a methyl substituent on the benzene ring of silicon, 4-tert-butyl styrene (denoted as 2c, 0.2mmol, 32.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a compound of the structure shown in formula 3z with an isolation yield of 77%.

[0257] The chemical reaction formula of the above preparation process is:

[0258]

[0259] The characterization data are:

[0260] 1 H NMR(400MHz,Chloroform-d)δ7.52(d,J=7.5Hz,1H),7.49–7.41(m,4H),7.41–7.36(m,2H),7.34(d,J=7.4Hz,1H),7.21 (d,J=7.6Hz,4H),6.96(d,J=19.1Hz,1H),6.79(d,J=19.1Hz,1H),2.40(s,3H),2.36(s,3H),1.35(s,9H),0.75(s,3H).

[0261] 13 C NMR(101MHz,Chloroform-d)δ151.6,146.4,144.6,139.2,136.4,135.6,135.2,134.9, 133.6,130.0,129.8,128.9,126.5,125.6,125.0,124.7,34.8,31.4,23.6,21.7,-2.5.

[0262] HRMS(ESI)m / z:[M+Na] + Calculate for C 27 H 32 NaSi + :407.2165; found:407.2163.

[0263] Embodiment 27

[0264] In a glove box filled with nitrogen, silicon-substituted bisphenyl heterocyclic silane (denoted as 1aa, 0.2mmol, 54.5mg), 4-tert-butyl styrene (denoted as 2c, 0.2mmol, 32.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 3aa, and the separation yield was 63%.

[0265] The chemical reaction formula of the above preparation process is:

[0266]

[0267] The characterization data are:

[0268] 1 H NMR (400MHz, Chloroform-d) δ7.61–7.53(m,4H),7.46–7.31(m,12H),7.25–7.19(m,1H),7.14(m,1H),6.96(d,J=1.5Hz,2H),2.25(s,3H),1.31(s,9H).

[0269] 13 C NMR (101MHz, Chloroform-d) δ151.8,148.2,145.2,136.0,135.6,135.1,130.2,130.2,128.1,126.6,125.6,125.1,122.3,34.8,31.4,24.0.

[0270] HRMS(ESI)m / z:[M+Na] + Calculate for C 31 H 32 NaSi + :455.2165; found:455.2155.

[0271] Embodiment 28

[0272] In a glove box filled with nitrogen, non-benzosilicon heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), styrene (denoted as 2a, 0.24mmol, 24.5mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5b with an isolation yield of 52%.

[0273] The chemical reaction formula of the above preparation process is:

[0274]

[0275] The characterization data are:

[0276] 1 H NMR(400MHz,Chloroform-d)δ7.69–7.58(m,4H),7.49(d,J=7.4Hz,2H),7.47–7.36(m,7H),7.34(d,J=7.6Hz,1H),7.30(d,J=1.5Hz ,1H),6.99(d,J=19.0Hz,1H),6.79(d,J=19.0Hz,1H),6.26(dq,J=18.2,6.0Hz,1H),6.10(d,J=18.4Hz,1H),1.96(d,J=6.1Hz,3H).

[0277] 13 C NMR(101MHz,Chloroform-d)δ148.3,148.3,138.2,135.7,135.5,135.5,135.4,129.5,129.5,128.7,128.5,128.1,128.0,126.8,125.4,123.8,23.1.

[0278] HRMS(ESI)m / z:[M+Na] + Calculate for C 23 H 22 NaSi + :349.1383; found:349.1391.

[0279] Embodiment 29

[0280] In a glove box filled with nitrogen, non-benzosilicon heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), styrene (denoted as 2c, 0.24mmol, 38.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5b with an isolation yield of 56%.

[0281] The chemical reaction formula of the above preparation process is:

[0282]

[0283] The characterization data are:

[0284] 1 H NMR(400MHz,Chloroform-d)δ7.65–7.60(m,4H),7.48–7.41(m,8H),7.39(s,2H),7.00(d,J=19.1Hz,1H) ,6.77(d,J=20.0Hz,1H),6.33–6.21(m,1H),6.11(d,J=17.0Hz,1H),1.97(d,J=6.0Hz,3H),1.36(s,9H).

[0285] 13 C NMR (101MHz, Chloroform-d) δ151.7,148.2,148.1,135.7,135.6,135.5,129.5,127.9,126.5,125.6,125.5,122.6,34.8,31.6,31.4,23.1.

[0286] HRMS (APCI) m / z: [M+Na] + Calculate for C 27 H 30 NaSi + :405.2009; found:405.2010.

[0287] Embodiment 30

[0288] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 4-methylstyrene (denoted as 2b, 0.24mmol, 28.3mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5c with an isolation yield of 51%.

[0289] The chemical reaction formula of the above preparation process is:

[0290]

[0291] The characterization data are:

[0292] 1 H NMR(400MHz,Chloroform-d)δ7.57(dd,J=7.6,1.8Hz,4H),7.40–7.36(m,5H),7.36(d,J=2.2Hz,3H),7.13(d,J=7.9Hz,2H),6.94(d,J =19.1Hz,1H),6.70(d,J=19.0Hz,1H),6.22(dq,J=18.2,6.0Hz,1H),6.07(d,J=18.4Hz,1H),2.34(s,3H),1.93(dd,J=6.1,1.5Hz,3H).

[0293] 13 C NMR (101MHz, Chloroform-d) δ148.2,148.2,138.5,135.7,135.6,135.5,129.5,129.4,127.9,126.8,125.6,122.4,23.1,21.4.

[0294] HRMS(APCI)m / z:[M+H] + Calculate for C 24 H 25 Si + :341.1720; found:341.1717.

[0295] Embodiment 31

[0296] In a glove box filled with nitrogen, non-benzosilicon heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 4-phenylstyrene (denoted as 2d, 0.24mmol, 43.2mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5d, and the separation yield was 45%.

[0297] The chemical reaction formula of the above preparation process is:

[0298]

[0299] The characterization data are:

[0300] 1 H NMR(400MHz,Chloroform-d)δ7.61–7.57(m,6H),7.54(t,J=7.4Hz,4H),7.43(d,J=7.5Hz,2H),7.40–7.36(m,5H),7.36–7.29(m, 2H), 7.01 (d, J = 19.1Hz, 1H), 6.81 (d, J = 19.1Hz, 1H), 6.24 (dt, J = 18.1, 6.0Hz, 1H), 6.08 (d, J = 18.4Hz, 1H), 1.94 (d, J = 6.0Hz, 3H).

[0301] 13 C NMR(101MHz,Chloroform-d)δ148.3,147.8,141.3,140.8,137.3,135.7,135.5 ,135.5,129.5,128.9,128.0,127.5,127.4,127.3,127.1,125.5,124.0,23.1.

[0302] HRMS(APCI)m / z:[M+H] + Calculate for C 29 H 27 Si + :403.1877; found:403.1874.

[0303] Embodiment 32

[0304] In a nitrogen-filled glove box, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2 mmol, 44.9 mg), 4-methoxystyrene (denoted as 2e, 0.24 mmol, 32.2 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M inTHF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnet and stirred at 120°C for 12 h. The resulting reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as an eluent, the solvent was decompressed and dried to obtain a compound of formula 5e with an isolated yield of 53%.

[0305] The chemical reaction formula of the above preparation process is:

[0306]

[0307] The characterization data are:

[0308] 1 H NMR(400MHz,Chloroform-d)δ7.60(dd,J=7.6,1.9Hz,4H),7.44(d,J=8.9Hz,3H),7.39(t,J=5.9Hz,5H),6.93(d,J=19.1Hz,1H),6.88(d,J =8.7Hz,2H),6.62(d,J=19.0Hz,1H),6.25(dq,J=18.2,6.0Hz,1H),6.09(dd,J=18.3,1.6Hz,1H),3.83(s,3H),1.95(dd,J=6.0,1.5Hz,3H).

[0309] 13 C NMR (101MHz, Chloroform-d) δ160.0,148.1,147.7,135.7,135.7,131.2,129.4,128.1,127.9,125.6,120.7,114.0,55.5,23.1.

[0310] HRMS(ESI)m / z:[M+Na] + Calculate for C 24 H 24 NeA + :379.1489; found:379.1494.

[0311] Embodiment 33

[0312] In a nitrogen-filled glove box, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 4-phenoxystyrene (denoted as 2f, 0.24mmol, 47.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M inTHF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as the eluent, the solvent was decompressed and dried to obtain the structural compound represented by formula 5f with an isolation yield of 39%.

[0313] The chemical reaction formula of the above preparation process is:

[0314]

[0315] The characterization data are:

[0316] 1 H NMR(400MHz,Chloroform-d)δ7.61–7.57(m,6H),7.54(t,J=7.4Hz,4H),7.43(d,J=7.5Hz,2H),7.40–7.36(m,5H),7.36–7.29(m, 2H), 7.01 (d, J = 19.1Hz, 1H), 6.81 (d, J = 19.1Hz, 1H), 6.24 (dt, J = 18.1, 6.0Hz, 1H), 6.08 (d, J = 18.4Hz, 1H), 1.94 (d, J = 6.0Hz, 3H).

[0317] 13 C NMR(101MHz,Chloroform-d)δ148.3,147.8,141.3,140.8,137.3,135.7,135.5 ,135.5,129.5,128.9,128.0,127.5,127.4,127.3,127.1,125.5,124.0,23.1.

[0318] HRMS(APCI)m / z:[M+H] + Calculate for C 29 H 27 Si + :403.1877; found:403.1874.

[0319] Embodiment 34

[0320] In a nitrogen-filled glove box, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 4-trimethylsilylstyrene (denoted as 2h, 0.24mmol, 42.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0Min THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 5g. The separation yield was 47%.

[0321] The chemical reaction formula of the above preparation process is:

[0322]

[0323] The characterization data are:

[0324] 1H NMR(400MHz,Chloroform-d)δ7.58(dd,J=7.7,1.7Hz,4H),7.51(d,J=8.1Hz,2H),7.46(d,J=8.2Hz,2H),7.38(dd,J=7.4,6.0Hz,6H),6.97 (d,J=19.1Hz,1H),6.81(d,J=19.0Hz,1H),6.23(dq,J=18.2,6.0Hz,1H),6.08(d,J=18.4Hz,1H),1.94(dd,J=6.0,1.5Hz,3H),0.27(s,9H).

[0325] 13 C NMR (101MHz, Chloroform-d) δ148.31,148.25,141.1,138.5,135.7,135.4,133.7,129.5,128.0,126.1,125.4,124.1,23.1,-1.0.

[0326] HRMS(ESI)m / z:[M+Na] + Calculate for C 26 H 30 NaSi2 + :421.1778; found:421.1766.

[0327] Embodiment 35

[0328] In a nitrogen-filled glove box, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 3-methylstyrene (denoted as 2j, 0.24mmol, 26.9g), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5h with an isolation yield of 48%.

[0329] The chemical reaction formula of the above preparation process is:

[0330]

[0331] The characterization data are:

[0332] 1 H NMR(400MHz,Chloroform-d)δ7.60–7.56(m,4H),7.40–7.34(m,6H),7.27(d,J=10.2Hz,3H),7.08(d,J=7.4Hz,1H),6.95( d,J=19.7Hz,1H),6.76(d,J=19.1Hz,1H),6.31–6.16(m,1H),6.07(d,J=18.4Hz,1H),2.34(s,3H),1.93(d,J=5.8Hz,3H).

[0333] 13 C NMR (101MHz, Chloroform-d) δ148.5,148.2,138.2,138.2,135.7,135.5,129.5,129.3,128.6,128.0,127.5,125.5,124.0,123.5,23.1,21.5.

[0334] HRMS(ESI)m / z:[M+Na]+calcd for C 24 H 24 SiNa+:363.1539; found:363.1537.

[0335] Embodiment 36

[0336] In a nitrogen-filled glove box, non-benzosilicon heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 2-methylstyrene (denoted as 2l, 0.24mmol, 28.3mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5i with an isolation yield of 45%.

[0337] The chemical reaction formula of the above preparation process is:

[0338]

[0339] The characterization data are:

[0340] 1 H NMR(400MHz,Chloroform-d)δ7.59(dd,J=9.8,2.5Hz,5H),7.42–7.37(m,5H),7.35(d,J=1.5Hz,1H),7.24(d,J=1.8Hz,1H),7.20–7.16(m,2H ),7.15–7.10(m,1H),6.66(d,J=19.0Hz,1H),6.24(dt,J=18.2,6.1Hz,1H),6.08(d,J=18.4Hz,1H),2.27(s,3H),1.93(dd,J=6.1,1.5Hz,3H).

[0341] 13 C NMR (101MHz, Chloroform-d) δ148.2,146.5,137.7,135.8,135.7,135.6,135.4,130.5,129.5,128.2,128.0,126.2,125.7,125.5,23.1,19.7.

[0342] HRMS(ESI)m / z:[M+Na] + Calculate for C 24 H 24 SiNa + :363.1539; found:363.1555.

[0343] Embodiment 37

[0344] In a glove box filled with nitrogen, non-benzosilicon heterocyclic silane (denoted as 4a, 0.2mmol, 44.9mg), 3,4-dimethylstyrene (denoted as 2w, 0.24mmol, 39.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M inTHF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain the structural compound represented by formula 5j. The separation yield was 42%.

[0345] The chemical reaction formula of the above preparation process is:

[0346]

[0347] The characterization data are:

[0348] 1 H NMR(400MHz,Chloroform-d)δ7.63–7.54(m,4H),7.35(m,6H),7.26–7.16(m,2H),7.06(m,1H),6.93(d,J=19.1Hz,1H),6.71(d,J= 19.0Hz, 1H), 6.30–6.16 (dq, J=18.3, 6.1Hz, 1H), 6.07 (dd, J=18.4Hz, 1.4Hz, 1H), 2.22 (s, 6H), 1.94–1.88 (dd, J=6.0, 1.5Hz, 3H).

[0349] 13 C NMR (101MHz, Chloroform-d) δ148.4,148.1,137.2,136.7,136.0,135.7,135.6,129.9,129.5,128.1,127.9,125.7,124.3,122.1,23.1,19.9,19.7.

[0350] HRMS(ESI)m / z:[M+H] + Calculate for C 25 H 27 Si + :355.1877; found:355.1882.

[0351] Embodiment 38

[0352] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane containing a substituent on the benzene ring (denoted as 4b, 0.2mmol, 50.5mg), 4-trimethylsilylstyrene (denoted as 2h, 0.24mmol, 42.4mg), a titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5k with an isolation yield of 45%.

[0353] The chemical reaction formula of the above preparation process is:

[0354]

[0355] The characterization data are:

[0356] 1 H NMR (400MHz, Chloroform-d) δ7.55–7.44(m,8H),7.21(d,J=7.6Hz,4H),6.98(d,J=19.1Hz,1H),6.81(d,J=19.0Hz,1H ), 6.23 (dq, J=18.3, 6.1Hz, 1H), 6.07 (dd, J=18.3, 1.4Hz, 1H), 2.39 (s, 6H), 1.94 (dd, J=6.1, 1.5Hz, 3H), 0.28 (s, 9H).

[0357] 13 C NMR (101MHz, Chloroform-d) δ148.9,148.8,141.9,140.4,139.7,136.8,134.7,133.0,129.8,127.1,126.9,125.7,24.1,22.7.

[0358] HRMS(ESI)m / z:[M+H] + Calculate for C 28 H 35 Si2 + :427.2272; found:427.2264.

[0359] Embodiment 39

[0360] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane containing substituents on the benzene ring (denoted as 4b, 0.2mmol, 50.5mg), 3-methoxystyrene (denoted as 2k, 0.24mmol, 32.2mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as the eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 5l with an isolation yield of 41%.

[0361] The chemical reaction formula of the above preparation process is:

[0362]

[0363] The characterization data are:

[0364] 1 H NMR(400MHz,Chloroform-d)δ7.49–7.43(m,4H),7.24(d,J=4.7Hz,1H),7.20(t,J=7.0Hz,4H),7.05(d,J=7.6Hz,1H),7.00(s,1H),6.92(d,J=19.0H z,1H),6.84–6.79(m,1H),6.74(d,J=19.0Hz,1H),6.27–6.14(m,1H),6.05 (d,J=18.3Hz,1H),3.81(s,3H),2.36(s,6H),1.92(dd,J=6.1,1.6Hz,3H).

[0365] 13 C NMR (101MHz, Chloroform-d) δ160.0,147.9,147.7,139.8,139.4,135.8,131.9,129.6,128.8,125.9,124.8,119.6,114.4,111.7,55.4,23.1,21.7.

[0366] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H 29 OSi + :385.1982; found:385.1986.

[0367] Embodiment 40

[0368] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane containing substituents on the benzene ring (denoted as 4b, 0.2mmol, 50.5mg), 2-methoxystyrene (denoted as 2m, 0.24mmol, 32.2mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether / ethyl acetate (100:1) as the eluent, the solvent was decompressed and dried to obtain the structural compound shown in formula 5m with an isolation yield of 43%.

[0369] The chemical reaction formula of the above preparation process is:

[0370]

[0371] The characterization data are:

[0372] 1 H NMR(400MHz,Chloroform-d)δ7.58–7.43(m,5H),7.37–7.24(m,7H),7.20–7.12(m,1H),6.90–6.84(m,1H),6.78(m,1H),6. 67(d,J=19.3Hz,1H),6.15(dq,J=18.1,6.0Hz,1H),6.01(dd,J=18.4,1.5Hz,0H),3.71(s,3H),1.85(dd,J=6.0,1.4Hz,3H).

[0373] 13 C NMR (101MHz, Chloroform-d) δ157.0,148.1,142.8,135.8,135.7,129.5,129.4,127.9,127.5,126.8,125.6,124.1,120.7,111.2,55.6,23.1.

[0374] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H 29 OSi + :385.1982; found:385.2000 Example 41

[0375] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane containing a substituent on the benzene ring (denoted as 4c, 0.2mmol, 50.5mg), 4-trimethylsilylstyrene (denoted as 2h, 0.24mmol, 42.4mg), a titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5n with an isolation yield of 44%.

[0376] The chemical reaction formula of the above preparation process is:

[0377]

[0378] The characterization data are:

[0379] 1 H NMR(400MHz,Chloroform-d)δ7.66–7.51(m,5H),7.49(d,J=8.1Hz,3H),7.41(d,J=8.2Hz,4H),7.01(d,J=19.1Hz,1H),6.82 (d,J=19.0Hz,1H),6.30–6.18(m,1H),6.08(dd,J=18.3,1.6Hz,1H),1.94(dd,J=6.0,1.5Hz,3H),1.34(s,18H),0.28(s,9H).

[0380] 13 C NMR (101MHz, Chloroform-d) δ153.3,148.8,148.8,141.9,139.7,136.6,134.7,133.0,127.1,126.9,125.9,125.8,35.8,32.4,24.1,0.0.

[0381] HRMS(ESI)m / z:[M+H] + Calculate for C 34 H 47 Si2 + :511.3211; found:511.3208.

[0382] Embodiment 42

[0383] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane containing a substituent on the benzene ring (denoted as 4d, 0.2mmol, 78.5mg), 4-trimethylsilylstyrene (denoted as 2h, 0.24mmol, 42.4mg), a titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5o with an isolation yield of 37%.

[0384] The chemical reaction formula of the above preparation process is:

[0385]

[0386] The characterization data are:

[0387] 1 H NMR(400MHz,Chloroform-d)δ7.50–7.44(m,4H),7.40(d,J=8.2Hz,2H),7.34(d,J=6.5Hz,2H),7.12(d,J=2.0Hz,2H),7.10(s,2H),6.8 5(d,J=19.1Hz,1H),6.63(d,J=17.1Hz,1H),6.29–6.05(m,1H),5.93(dd,J=18.6,1.6Hz,1H),1.83(dd,J=6.2,1.5Hz,3H),0.15(s,9H).

[0388] 13 C NMR(101MHz,Chloroform-d)δ150.7,149.4,149.2,141.7,138.2,137.3,133.8,126.2,124.5,122.7,121.9,120.4,23.1,-1.1.19F NMR(376MHz,Chloroform-d)δ-57.54.

[0389] HRMS(ESI)m / z:[M+Na] + Calculate for C 28 H 28 F6O2Si2Na + :589.1424; found:589.1402.

[0390] Embodiment 43

[0391] In a nitrogen-filled glove box, thiophene-substituted non-benzosilyl heterocyclic silane (denoted as 4e, 0.2mmol, 47.3mg), 4-trimethylsilylstyrene (denoted as 2h, 0.24mmol, 42.4mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 120°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a compound of formula 5p with a separation yield of 55%.

[0392] The chemical reaction formula of the above preparation process is:

[0393]

[0394] The characterization data are:

[0395] 1 H NMR(400MHz,Chloroform-d)δ7.68(dd,J=4.6,0.9Hz,2H),7.44–7.39(m,4H),7.38–7.34(m,2H),7.24–7.22(m,2H),7.06(d,J= 19.0Hz,1H),6.67(d,J=19.0Hz,1H),6.41–6.27(m,1H),6.05(dd,J=18.4,1.6Hz,1H),1.93(dd,J=6.2,1.6Hz,3H),1.31(s,9H).

[0396] 13 C NMR (101MHz, Chloroform-d) δ152.0,148.7,148.4,137.1,135.3,134.8,132.3,128.4,126.7,125.6,125.5,122.1,34.8,31.6,31.4,23.0.

[0397] HRMS(ESI)m / z:[M+H] + Calculate for C 23 H 27 S2S + :395.1318; found:395.1315.

[0398] Embodiment 44

[0399] In a glove box filled with nitrogen, non-benzosilyl heterocyclic silane (denoted as 4a, 0.2 mmol, 44.9 mg), 2-(1-(4-tert-butylphenyl)vinyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (denoted as 2aa, 0.24 mmol, 68.7 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 M in THF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 120° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 5q with an isolation yield of 23%.

[0400] The chemical reaction formula of the above preparation process is:

[0401]

[0402] The characterization data are:

[0403] 1 H NMR(400MHz,Chloroform-d)δ7.62–7.53(m,4H),7.49–7.41(m,2H),7.33(m,8H),7.07(s,1H),6.21(dd,J =18.4,1.5Hz,1H),6.06(dq,J=18.3,6.0Hz,1H),1.89(dd,J=6.1,1.5Hz,3H),1.31(s,12H),0.98(s,9H).

[0404] 13 C NMR(101MHz,Chloroform-d)δ148.3,145.2,140.9,140.1,135.5,133.6,133.3,126.9,125.7,125.5,124.9,123.2,82.0,32.6,29.5,22.8,21.1.11B NMR(128MHz,Chloroform-d)δ29.93.

[0405] HRMS(ESI)m / z:[M+H] + Calculate for C 33 H 42 BO2Si + :509.3042; found:509.3052.

[0406] Embodiment 45

[0407] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), trimethyl(vinyl)silane (denoted as 6a, 0.2mmol, 20.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 7a, and the separation yield was 54%.

[0408] The chemical reaction formula of the above preparation process is:

[0409]

[0410] The characterization data are:

[0411] 1 H NMR(400MHz,Chloroform-d)δ7.51–7.45(m,2H),7.43(m,1H),7.39–7.29(m,4H),7.17(m,2 H),6.95(d,J=22.4Hz,1H),6.76(d,J=22.5Hz,1H),2.28(s,3H),0.65(s,3H),0.09(s,9H).

[0412] 13 C NMR (101MHz, Chloroform-d) δ155.1,146.2,144.6,137.3,136.3,135.0,134.8,130.2,129.8,129.2,128.0,125.0,23.6,-1.5,-3.1.

[0413] HRMS(ESI)m / z:[M+Na] + Calculate for C 19 H 26 Si2Na + :333.1465; found:333.1463.

[0414] Embodiment 46

[0415] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2 mmol, 42.0 mg), diethyl(methyl)(vinyl)silane (denoted as 6b, 0.2 mmol, 25.7 mg), titanium catalyst (10 mol%, 6.9 mg) and PhMgBr (1.0 Min THF, 10 mol%, 20 μL) were mixed in a 15 mL pressure tube with a magnet, and stirred at 100 ° C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 7b, and the separation yield was 62%.

[0416] The chemical reaction formula of the above preparation process is:

[0417]

[0418] The characterization data are:

[0419] 1 H NMR(400MHz,Chloroform-d)δ7.50(s,2H),7.46(d,J=5.8Hz,1H),7.42–7.30(m,4H),7.20(s,2H),7.00(d,J=22 .6Hz,1H),6.76(d,J=22.6Hz,1H),2.32(s,3H),1.01–0.93(m,6H),0.68(s,3H),0.65–0.56(m,4H),0.08(s,3H).

[0420] 13 C NMR (101MHz, Chloroform-d) δ152.8,147.7,144.6,137.4,136.3,135.1,134.9,130.0,129.8,129.2,128.0,125.0,23.5,7.6,5.3,-3.0,-6.3.

[0421] HRMS(APCI)m / z:[M+H] + Calculate for C 21 H 31 Si2 + :339.1959; found:339.1966.

[0422] Embodiment 47

[0423] In a glove box filled with nitrogen, silanol (denoted as 1a, 0.2mmol, 42.0mg), dimethyl(phenyl)(vinyl)silane (denoted as 6c, 0.2mmol, 32.5mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0Min THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 7c with an isolation yield of 47%.

[0424] The chemical reaction formula of the above preparation process is:

[0425]

[0426] The characterization data are:

[0427] 1 H NMR(400MHz,Chloroform-d)δ7.55–7.47(m,4H),7.43(dd,J=7.7,1.6Hz,1H),7.39–7.35(m,5H),7.34–7.29(m, 2H),7.20–7.15(m,2H),7.06(d,J=22.4Hz,1H),6.87(d,J=22.5Hz,1H),2.28(s,3H),0.66(s,3H),0.37(s,6H).

[0428] 13 C NMR(101MHz,Chloroform-d)δ152.2,148.6,144.5,138.4,137.0,136.2,134. 7,133.9,129.9,129.8,129.1,129.0,127.9,127.8,124.9,23.4,-2.9,-3.2.

[0429] HRMS(APCI)m / z:[M+H] + Calculate for C 24 H 29 Si2 + :373.1802; found:373.1813.

[0430] Embodiment 48

[0431] In a glove box filled with nitrogen, silicon-substituted bisphenyl heterocyclic silane (denoted as 1aa, 0.2mmol, 54.5mg), trimethyl(vinyl)silane (denoted as 6a, 0.2mmol, 20.0mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 7d with an isolation yield of 39%.

[0432] The chemical reaction formula of the above preparation process is:

[0433]

[0434] The characterization data are:

[0435] 1 H NMR(400MHz,Chloroform-d)δ7.40(s,1H),7.39(d,J=1.7Hz,2H),7.33–7.28(m,4H),7.27–7.21(m,4H),7.14(d,J=1.5 Hz,1H),7.10(d,J=2.4Hz,1H),7.04(s,1H),7.01(d,J=9.7Hz,1H),6.71(d,J=22.5Hz,1H),2.11(s,3H),-0.00(s,9H).

[0436] 13 C NMR (101MHz, Chloroform-d) δ157.2,145.2,143.9,137.9,136.0,135.0,133.0,130.2,130.1,129.5,128.0,125.1,24.0,-1.5.

[0437] HRMS(ESI)m / z:[M+Na] + Calculate for C 24 H 29 Si2 + :395.1622; found:395.1624.

[0438] Embodiment 49

[0439] In a glove box filled with nitrogen, silicon-substituted bisphenyl heterocyclic silane (denoted as 1aa, 0.2mmol, 54.5mg), diethyl(methyl)(vinyl)silane (denoted as 6b, 0.2mmol, 25.7mg), titanium catalyst (10mol%, 6.9mg) and PhMgBr (1.0M in THF, 10mol%, 20μL) were mixed in a 15mL pressure tube with a magnet, and stirred at 100°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 7e with an isolation yield of 38%.

[0440] The chemical reaction formula of the above preparation process is:

[0441]

[0442] The characterization data are:

[0443] 1 H NMR(400MHz,Chloroform-d)δ7.51–7.46(m,4H),7.43–7.31(m,7H),7.25–7.17(m,3H),7.15–7.10(m ,1H),6.77(d,J=22.6Hz,1H),2.22(s,3H),0.93(t,J=7.9Hz,6H),0.59(q,J=7.6Hz,4H),0.06(s,3H).

[0444] 13 C NMR (101MHz, Chloroform-d) δ155.1,145.2,137.9,136.1,135.1,130.2,130.1,129.5,128.0,125.1,24.0,7.6,5.3,-6.3.

[0445] HRMS(ESI)m / z:[M+H] + Calculate for C 26 H 33 Si2 + :401.2115; found:401.2126.

[0446] Embodiment 50

[0447] In a nitrogen-filled glove box, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8a, 0.2 mmol, 37.7 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9a with an isolation yield of 68%.

[0448] The chemical reaction formula of the above preparation process is:

[0449]

[0450] The characterization data are:

[0451] 1 H NMR(400MHz,Chloroform-d)δ7.51(d,J=7.1Hz,1H),7.32–7.25(m,1H),7.24–7.07(m,2H),6.17(dq,J=18.5,6.2Hz,1H),5.76(d,J= 18.4Hz, 1H), 3.08 (t, J = 7.4Hz, 2H), 1.83 (d, J = 6.1Hz, 3H), 1.10 (dt, J = 14.6, 7.3Hz, 1H), 0.99 (dt, J = 14.9, 7.5Hz, 1H), 0.34 (s, 3H).

[0452] 13 C NMR (101MHz, Chloroform-d) δ153.7,144.9,138.9,132.5,129.4,128.4,125.8,31.9,22.8,11.0,-3.4.

[0453] HRMS(ESI)m / z:[M+Na] + Calculate for C 12 H 16 SiNa + :211.0913; found:211.0906.

[0454] Embodiment 51

[0455] In a nitrogen-filled glove box, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8b, 0.2 mmol, 40.5 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9b with an isolation yield of 71%.

[0456] The chemical reaction formula of the above preparation process is:

[0457]

[0458] The characterization data are:

[0459] 1 H NMR(400MHz,Chloroform-d)δ7.32(s,1H),7.17–7.07(m,2H),6.17(dq,J=18.4,6.1Hz,1H),5.76(d,J=18.4Hz,1H),3.03(t,J=7.3H z, 2H), 2.33 (d, J = 3.3Hz, 3H), 1.83 (dd, J = 6.1, 1.7Hz, 3H), 1.09 (dt, J = 14.6, 7.2Hz, 1H), 0.97 (dt, J = 14.8, 7.4Hz, 1H), 0.33 (s, 3H).

[0460] 13 C NMR (101MHz, Chloroform-d) δ150.8,144.8,138.9,135.0,132.9,130.5,128.5,125.6,31.4,22.8,21.2,11.2,-3.4.

[0461] HRMS(ESI)m / z:[M+H] + Calculate for C 13 H 19 Si + :203.1251; found:203.1249.

[0462] Embodiment 52

[0463] In a glove box filled with nitrogen, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8c, 0.2 mmol, 43.7 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9c with an isolation yield of 53%.

[0464] The chemical reaction formula of the above preparation process is:

[0465]

[0466] The characterization data are:

[0467] 1 H NMR(400MHz,Chloroform-d)δ7.42(d,J=8.8Hz,1H),6.81–6.75(m,2H),6.15(dq,J=18.4,6.2Hz,1H),5.76(d,J=18.4Hz,1H),3. 80(s,3H),3.06(t,J=7.3Hz,2H),1.83(d,J=6.1Hz,3H),1.10(dt,J=14.6,7.3Hz,1H),1.00(dt,J=15.0,7.5Hz,1H),0.33(s,3H).

[0468] 13 C NMR (101MHz, Chloroform-d) δ161.3,156.1,144.7,133.5,129.8,128.8,112.8,110.6,55.2,32.1,22.8,11.4,-3.1.

[0469] HRMS(ESI)m / z:[M+Na] + Calculate for C 13 H 18 OSi + :241.1019; found:241.1020.

[0470] Embodiment 53

[0471] In a glove box filled with nitrogen, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8d, 0.2 mmol, 40.5 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9d. The separation yield was 75%.

[0472] The chemical reaction formula of the above preparation process is:

[0473]

[0474] The characterization data are:

[0475] 1 H NMR(400MHz,Chloroform-d)δ7.42(d,J=7.3Hz,1H),7.09(s,1H),7.04(d,J=7.3Hz,1H),6.17(dq,J=18.4,6.2Hz,1H),5.76(d,J=18.5Hz ,1H),3.06(t,J=7.4Hz,2H),2.34(s,3H),1.83(d,J=6.2Hz,3H),1.10(dt,J=14.6,7.3Hz,1H),0.99(dt,J=14.9,7.4Hz,1H),0.34(s,3H).

[0476] 13 C NMR (101MHz, Chloroform-d) δ154.2,144.8,139.4,135.3,132.4,128.6,126.9,126.5,31.8,22.8,21.7,11.2,-3.3.

[0477] HRMS(APCI)m / z:[M+H] + Calculate for C 13 H 19 Si + :203.1251; found:203.1252.

[0478] Embodiment 54

[0479] In a glove box filled with nitrogen, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8d, 0.2 mmol, 43.7 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 100 mol%, 200 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9d with an isolation yield of 41%.

[0480] The chemical reaction formula of the above preparation process is:

[0481]

[0482] The characterization data are:

[0483] 1 H NMR(400MHz,Chloroform-d)δ7.23(d,J=7.5Hz,1H),6.82(dd,J=7.5,0.9Hz,1H),6.60(d,J=8.0Hz,1H),6.15(dq,J=18.5,6.2Hz,1H), 5.78(d,J=18.4Hz,1H),3.76(s,3H),3.02(t,J=7.6Hz,2H),1.80(d,J=6.2Hz,3H),1.13–0.97(m,1H),0.95–0.86(m,1H),0.36(s,3H).

[0484] 13 C NMR (101MHz, Chloroform-d) δ163.7,155.8,144.0,131.5,128.3,126.4,118.5,106.7,55.2,31.9,22.7,10.5,-3.2.

[0485] HRMS(ESI)m / z:[M+H] + Calculate for C 13 H 19 OSi + :219.1200; found:219.1193.

[0486] Embodiment 55

[0487] In a nitrogen-filled glove box, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8f, 0.2 mmol, 41.3 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9f with an isolation yield of 71%.

[0488] The chemical reaction formula of the above preparation process is:

[0489]

[0490] The characterization data are:

[0491] 1 H NMR (400MHz, Chloroform-d) δ7.23–7.13(m,2H),6.98(ddd,J=9.1,8.3,2.7Hz,1H),6.20(dq,J=18.5,6.2Hz,1H),5.76(d,J=18. 5Hz,1H),3.05(t,J=7.4Hz,2H),1.86(d,J=7.9Hz,3H),1.16(dt,J=14.7,7.2Hz,1H),1.05(dt,J=14.9,7.4Hz,1H),0.36(s,3H).

[0492] 13 C NMR(101MHz,Chloroform-d)δ161.7(d,J=245.1Hz),148.8(d,J=2.4Hz),145.5,141.5(d,J=4.6Hz) ,127.7,126.9(d,J=7.2Hz),118.1(d,J=18.6Hz),116.5(d,J=22.2Hz),31.1,22.8,11.6,-3.6.19F NMR(376MHz,Chloroform-d)δ-118.81.

[0493] HRMS(APCI)m / z:[M+H] + Calculate for C 12 H 16 F + :207.1000; found:207.1003.

[0494] Embodiment 56

[0495] In a glove box filled with nitrogen, ortho-olefin-substituted silyl heterocyclic silyl butane (8 g, 0.2 mmol, 47.7 mg), titanium catalyst (10 mol%, 6.9 mg) and CH3MgBr (1.0 M in THF, 20 mol%, 40 μL) were mixed in a 15 mL pressure tube with a magnetic device, and stirred at 80° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as an eluent, the solvent was decompressed and dried to obtain a compound of formula 9g with a separation yield of 35%.

[0496] The chemical reaction formula of the above preparation process is:

[0497]

[0498] The characterization data are:

[0499] 1 H NMR (400MHz, Chloroform-d) δ7.85 (ddd, J=7.7, 6.0, 1.4Hz, 2H), 7.80 (d, J=8.3Hz, 1H), 7.51–7.42 (m, 2H), 7.38 (d, J=8.4Hz, 1H), 6.27 (dq, J=18. 5,6.2Hz,1H),5.93(d,J=18.4Hz,1H),3.27(t,J=7.3Hz,2H),1.86(d,J=6 .2Hz,3H),1.27–1.18(m,1H),1.11(dt,J=14.9,7.6Hz,1H),0.54(s,3H).

[0500] 13 C NMR (101MHz, Chloroform-d) δ153.3,145.1,136.7,136.1,132.3,130.2,128.9,128.6,128.5,126.2,125.0,124.9,32.7,22.9,10.3,-2.8.

[0501] HRMS(ESI)m / z:[M+H] + Calculate for C 16 H 19 Si + :239.1251; found:239.1246.

[0502] Embodiment 57

[0503] In a glove box filled with nitrogen, ortho-olefin-substituted silyl heterocyclic silyl butane (denoted as 8h, 0.2mmol, 49.7mg), titanium catalyst (10mol%, 6.9mg) and CH3MgBr (1.0M in THF, 100mol%, 200μL) were mixed in a 15mL pressure tube with a magnet and stirred at 80°C for 12h. The obtained reaction solution was purified by silica gel column chromatography. After elution with petroleum ether as eluent, the solvent was decompressed and dried to obtain a structural compound represented by formula 9h with an isolation yield of 45%.

[0504] The chemical reaction formula of the above preparation process is:

[0505]

[0506] The characterization data are:

[0507] 1 H NMR(400MHz,Chloroform-d)δ6.96(s,1H),6.78(s,1H),6.17(dq,J=18.5,6.2Hz,1H),5.77(d,J=18.4Hz,1H),3.89(s,3H),3.8 7(s,3H),3.03(t,J=7.3Hz,2H),1.84(d,J=6.2Hz,3H),1.10(dt,J=14.6,7.2Hz,1H),1.00(dt,J=14.9,7.5Hz,1H),0.34(s,3H).

[0508] 13 C NMR (101MHz, Chloroform-d) δ150.7,147.8,146.9,144.7,129.2,128.8,113.8,108.6,56.1,55.8,31.7,22.8,11.3,-3.1.

[0509] HRMS(ESI)m / z:[M+H] + Calculate for C 14 H 21 O2Si + :249.1305; found:249.1305.

Claims

1. A method for preparing an alkenyl silane compound, characterized in that: The method is that under a protective atmosphere, silacyclobutane compounds, olefin compounds, a catalytic amount of a titanium catalyst and a catalytic amount of a tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide are reacted at 100 to 120° C., and after reacting for 12 to 24 hours, column chromatography purification is performed to obtain a plurality of differently substituted alkenylsilane compounds.

2. The method for preparing an alkenyl silane compound according to claim 1, characterized in that: The molar ratio of the silacyclobutane compound to the olefin compound is 1:1-1:1.2 or 1.2:

1.

3. The method for preparing an alkenyl silane compound according to claim 2, characterized in that: The silacyclobutane compound is benzosilacyclobutane or silacyclobutane; The benzosilacyclobutane has the following structural formula: The silacyclobutane has the following structural formula: Where: R 1 , R 2 is one of methyl and substituted phenyl; R 3 is a fluorine atom or a hydrogen atom; Aryl is an aryl group or an aromatic heterocycle.

4. The method for preparing an alkenyl silane compound according to claim 3, characterized in that: The R 1 or R 2 is one of methyl, phenyl and 4-methylphenyl; Aryl is one of phenyl, 4-methylphenyl, 4-trifluoromethoxyphenyl, 4-tert-butylphenyl and thienyl.

5. The method for preparing an alkenyl silane compound according to claim 2, characterized in that: The olefin compound is a substituted styrene or a substituted vinyl silane; The substituted styrenes have the following structural formula: The substituted vinyl silanes have the following structural formula: Where: R 4 is methyl; R 5 is methyl or ethyl; R 6 It is methyl or phenyl.

6. The method for preparing an alkenyl silane compound according to claim 5, characterized in that: The substituted styrenes are 4-methylstyrene, 4-methoxystyrene, 4-tert-butylstyrene, 4-phenylstyrene, 4-fluorostyrene, 4-phenoxystyrene, 4-N,N-dimethylstyrene, 4-trimethylsilylstyrene, 4-vinylstyrene, 3-methylstyrene, 3-methoxystyrene, 2-methylstyrene, 2-methoxystyrene, 2-fluorostyrene, 2-vinylnaphthalene, 3-vinylbicyclo[4.2.0]octa-1,3,5-triene, vinylferrocene, 3,4-dimethylstyrene, 3 , 4-dimethoxystyrene, 3,4,5-trimethoxystyrene, (2-(4-vinylphenyl)ethylene-1,1,2-triyl)triphenyl, 1,3,3-trimethyl-2-(4-vinylphenoxy)bicyclo[2.2.1]heptane, 1-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)-4-vinylbenzene; the substituted vinyl silane is one of trimethyl(vinyl)silane, dimethyl(phenyl)(vinyl)silane, and diethyl(methyl)(vinyl)silane.

7. The method for preparing an alkenyl silane compound according to claim 1, characterized in that: The amount of the titanium catalyst used is 10 mol% of the amount of the silacyclobutane compound used.

8. The method for preparing an alkenyl silane compound according to claim 1, characterized in that: The concentration of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 1.0 mol / L, and the amount of the tetrahydrofuran solution of phenylmagnesium bromide or methylmagnesium bromide is 10-20 mol% of the amount of the silacyclobutane compound.

9. The method for preparing an alkenyl silane compound according to claim 1, characterized in that: The eluent used for column chromatography purification is petroleum ether, or a mixed solution of petroleum ether and ethyl acetate uniformly mixed in a volume ratio of 50:1 to 100:

1.

10. The method for preparing an alkenyl silane compound according to claim 1, characterized in that: The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

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