Preparation method of alkyl trihydrosilane and methyl alkyl dihydrosilane

Abstract

The invention relates to a preparation method of alkyl trihydrosilane and methyl alkyl dihydrosilane, which is characterized in that the method comprises the following steps: in a protective atmosphere, an olefin compound, a silane compound and a Cp2ZrH2 catalyst are subjected to a hydrosilylation reaction at 100 DEG C for 12 hours, and then rapid column chromatography purification is performed to obtain a second-stage or third-stage silane compound. And carrying out silicon-boron functional group exchange reaction on the obtained second-stage or third-stage silane compound, a tetrahydrofuran solution (1.0 M) of BH3 and pinacolborane at 70 DEG C, and reacting for 12-48 hours to obtain the alkyl trihydrosilane and methyl alkyl dihydrosilane compound. The method is simple to operate and low in cost, is not only suitable for styrene substrates with higher activity, but also suitable for alkyl olefin substrates with lower activity, and the synthesized alkyl trihydrosilane and methyl alkyl dihydrosilane compounds are various in types, good in selectivity and beneficial to product separation and purification.

Description

Technical Field

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

[0002] Organosilane compounds are a class of rich and practical organic compounds. As an important intermediate in synthetic chemistry, they are widely used in research fields such as materials science and the pharmaceutical industry. Organosilane compounds have become compounds with extensive transformation and synthetic value due to their relative stability and wide reactivity. In recent years, 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. The methods for synthesizing organosilicon compounds usually include hydrosilylation of olefins, coupling reaction of Grignard reagents with chlorosilanes, etc. These methods have received relatively much attention and research, and have made great progress. However, the synthesis of alkyltrihydrosilane and methylalkyldihydrosilane compounds is relatively difficult to obtain using existing methods because they involve hydrosilylation of olefins with SiH4 and MeSiH3. The following are the main reasons that limit the application of SiH4 and MeSiH3 in hydrosilylation reactions: (1) SiH4 and MeSiH3 are pyrophoric and explosive toxic gases, requiring special equipment during use and handling; (2) The strong reducing ability of SiH4 and MeSiH3 easily leads to the deposition of metal catalysts, and usually only a low conversion rate can be obtained; (3) The product obtained after a one-step hydrosilylation reaction of SiH4 and MeSiH3 with olefins can further react with 1-3 moles of olefins, often obtaining a mixture of primary silane, secondary silane, tertiary silane and quaternary silane. To address these limitations, the Oesterich group developed the use of tri(cyclohexyl-2,5-di-1-yl)silane and di(cyclohexyl-2,5-di-1-yl)silane as silane alternatives for the "transfer hydrogen silylation reaction" (Nat. Chem. 2015, 7, 816-822; Chem 2018, 4, 1443-1450). However, we note that these two SiH4 alternatives are expensive and not easily available. In addition, the chemical selectivity for olefin hydrosilylation cannot be controlled, and mono(-SiH) or dihydrosilane (-SiH2) is obtained. There is only one example of the selective preparation of synthetically important but challenging alkyltrihydrosilanes (-SiH3), through Pt(0)-catalyzed olefin hydrosilylation and B(C6F5)3-catalyzed deprotection method (Nat. Chem. 2015, 7, 816-822). Therefore, although a lot of research results have been achieved in the method of synthesizing silanes, there are still great challenges in the high chemical selectivity synthesis of alkyltrihydrosilane and methylalkyldihydrosilane compounds. Summary of the invention

[0004] The technical problem to be solved by the present invention is to provide a method for preparing alkyltrihydrosilane and methylalkyldihydrosilane compounds with simple operation and low cost.

[0005] To solve the above problems, the present invention discloses a method for preparing alkyl trihydrosilane and methyl alkyl dihydrosilane compounds, characterized in that: the method is to carry out a hydrosilation reaction at 100°C with olefin compounds, silane compounds and Cp2ZrH2 catalyst under a protective atmosphere, and then perform rapid column chromatography purification after 12 hours to obtain a secondary or tertiary silane compound. The obtained secondary or tertiary silane compound, a tetrahydrofuran solution of BH3 (1.0M) and pinacol borane are subjected to a silicon-boron functional group exchange reaction at 70°C, and the alkyl trihydrosilane and methyl alkyl dihydrosilane compounds are obtained after 12 to 48 hours of reaction.

[0006] The molar ratio of the olefin compound to the silane compound is 1:1.2-1.5, and the molar ratio of the secondary or tertiary silane obtained in the first step to the pinacol borane is 1:1.3-2.

[0007] The olefin compound has one of the following structural formulas: RCH=CH2, wherein R is one of an aryl group, an aromatic heterocycle or an alkyl group.

[0008] The R is one of 2-naphthalene, ferrocene, phenyl, substituted phenyl or alkyl.

[0009] The substituent in the substituted phenyl group is one of methyl, methoxy, fluorine, chlorine, bromine, tert-butyl and trifluoromethyl.

[0010] The silane compound is phenylsilane or methylphenylsilane.

[0011] The amount of the Cp2ZrH2 catalyst used is 1 mol%, and the amount of the BH3 tetrahydrofuran solution (1.0 M) used is 10-20 mol%.

[0012] The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

[0013] Compared with the prior art, the present invention has the following advantages:

[0014] 1. The present invention uses a tetrahydrofuran solution (1.0 M) of cheap and readily available Cp2ZrH2 and BH3 as a catalyst, which greatly reduces the production cost.

[0015] 2. The first step of the Cp2ZrH2-catalyzed hydrosilylation reaction and the second step of the silicon-boron functional group exchange reaction of the present invention do not require the use of any organic solvent, which meets the requirements of green chemistry.

[0016] 3. The present invention does not use additives and can achieve a formal hydrosilylation reaction of olefins with SiH4 and MeSiH3 under relatively mild conditions with high chemical selectivity to obtain a series of alkyltrihydrosilane and methylalkyldihydrosilane compounds. The harsh reaction conditions, instruments and potential safety factors required for preparing the above compounds from olefins through hydrosilylation reaction with SiH4 and MeSiH3 are avoided.

[0017] 4. The present invention is simple to operate and low in cost, and is applicable not only to styrene-type substrates with higher activity, but also to alkyl olefins with lower activity.

[0018] 5. The alkyltrihydrosilane and methylalkyldihydrosilane compounds synthesized by the method of the present invention are of various types and have good chemical selectivity, which is conducive to the separation and purification of the products. DETAILED DESCRIPTION

[0019] A method for preparing alkyl trihydrosilane and methyl alkyl dihydrosilane, characterized in that: the method is to carry out a hydrosilation reaction at 100°C with olefin compounds, silane compounds, and Cp2ZrH2 catalyst under a protective atmosphere, and then perform rapid column chromatography purification after 12 hours to obtain a secondary or tertiary silane compound. The obtained secondary or tertiary silane compound, a tetrahydrofuran solution of BH3 (1.0M), and pinacol borane are subjected to a silicon-boron functional group exchange reaction at 70°C, and the alkyl trihydrosilane and methyl alkyl dihydrosilane compounds are obtained after 12 to 48 hours of reaction. Wherein: the molar ratio of the olefin compound to the silane compound is 1:1.2-1.5, the molar ratio of the secondary or tertiary silane obtained in the first step to the pinacol borane is 1:1.3-2; the amount of the Cp2ZrH2 catalyst is 1 mol%, and the amount of the tetrahydrofuran solution of BH3 (1.0M) is 10-20 mol%.

[0020] The reaction equation of the preparation method of alkyl trihydrosilane and methyl alkyl dihydrosilane in the present invention is:

[0021]

[0022] The olefin compound has one of the following structural formulas: RCH=CH2. R is one of aryl, aromatic heterocycle or alkyl. R is one of 2-naphthalene, ferrocene, phenyl, substituted phenyl or alkyl. The substituent in the substituted phenyl is one of methyl, methoxy, fluorine, chlorine, bromine, tert-butyl and trifluoromethyl, and the substitution position of the substituent is not particularly limited.

[0023] The olefin compound can be selected from styrene, 4-methylstyrene, 4-tert-butylstyrene, 4-methoxystyrene, 4-fluorostyrene, 4-chlorostyrene, 4-bromostyrene, 4-trifluoromethylstyrene, 2-vinylnaphthalene, allylbenzene, 4-phenyl-1-butene, 1-dodecene, 1-hexadecene, 4-vinyl-4'-pentyldicyclohexane, vinylferrocene, and n-decene.

[0024] The silane compounds are phenylsilane and methylphenylsilane.

[0025] In the present invention, the first step of mixing is preferably to mix olefin compounds, silane compounds and Cp2ZrH2 in a pressure tube; the second step of mixing is preferably to mix the secondary and tertiary silane products obtained by the first step of hydrosilation separation, pinacol borane and tetrahydrofuran solution of BH3 in a pressure tube.

[0026] In the present invention, pinacol borane needs to be carefully purified, and the method of adding the pinacol borane is not particularly limited and can be added in a manner well known to those skilled in the art.

[0027] In the present invention, the reaction is preferably 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.

[0028] 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.

[0029] The present invention also preferably includes separation. Since the alkyl trihydrosilane and methyl alkyl dihydrosilane obtained in the end have low boiling point, low polarity, and are easy to deteriorate, rapid column chromatography with a very small, low boiling point 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.

[0030] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0031] The novel method for preparing alkyltrihydrosilane and methylalkyldihydrosilane provided by the present invention is described in detail below in conjunction with the examples, but they should not be construed as limiting the scope of protection of the present invention.

[0032] Example 1

[0033] In a glove box filled with nitrogen, styrene (denoted as 1a, 5 mmol, 575 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in Formula 3a. Then, in a glove box filled with nitrogen, the above-obtained 3a (0.5 mmol, 106 mg), HBpin (1.0 mmol, 145 μL) and BH3.THF (1.0 MinTHF, 10 mol%, 50 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4a (colorless oil, phenethylsilane). The NMR yield was 91%, and the isolated yield was 62%.

[0034] The chemical reaction formula of the above preparation process is:

[0035]

[0036] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ7.34–7.22(m,2H),7.18(d,J=6.7Hz,3H),3.51(t,J=3.8Hz,3H),2.79–2.67(m,2H),1.10(dp,J=11.8,3.8Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ143.7,128.5,128.0,126.0,32.5,8.2. 29 SiNMR (79MHz, Chloroform- d )δ-58.87.HRMS(EI)m / z:[M+H] + calculation for C8H 13 Si + :137.0781; found:137.0735.

[0037] Example 2

[0038] In a glove box filled with nitrogen, 4-methylstyrene (denoted as 1b, 5 mmol, 659 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in Formula 3b. Then, in a glove box filled with nitrogen, the above-obtained 3b (0.5 mmol, 113 mg), HBpin (1.0 mmol, 145 μL) and BH3.THF (1.0 MinTHF, 10 mol%, 50 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a compound of formula 4b (colorless oil, 4-methylphenethylsilane). The NMR yield was 90%, and the separation yield was 59%.

[0039] The chemical reaction formula of the above preparation process is:

[0040]

[0041] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.10(s,4H),3.51(t,J=3.8Hz,3H),2.78–2.68(m,2H),2.33(s,3H),1.11(ddt,J=8.1,6.3,3.9Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ140.6,135.3,129.1,127.8,32.0,21.0,8.2. 29 SiNMR(79MHz,Chloroform-d)δ-58.97.HRMS(EI)m / z:[M+H] + Calcd for C9H 15 Si + :151.0938; found:151.0894.

[0042] Example 3

[0043] In a glove box filled with nitrogen, 4-tert-butylstyrene (denoted as 1c, 5 mmol, 916 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in formula 3c. Then, in a glove box filled with nitrogen, the above-obtained 3c (0.5mmol, 134mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a compound of formula 4c (colorless oil, 4-tert-butylphenylethylsilane). The NMR yield was 85%, and the isolated yield was 56%.

[0044] The chemical reaction formula of the above preparation process is:

[0045]

[0046] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.31(d,J=8.3Hz,2H),7.13(d,J=8.3Hz,2H),3.52( t,J=3.8Hz,3H),2.78–2.61(m,2H),1.31(s,9H),1.10(ddt,J=9.7,7.7,3.8Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ148.7,140.7,127.6,125.3,34.4,31.9,31.5,8.0. 29 SiNMR(79MHz,Chloroform-d)δ-58.74.HRMS(EI)m / z:[M+H] + calcdforC 12 H 21 Si + :193.1407; found:193.1364.

[0047] Example 4

[0048] In a glove box filled with nitrogen, 4-methoxystyrene (denoted as 1d, 5mmol, 665μL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 with the structure shown in formula 3d. Then, in a glove box filled with nitrogen, the above-obtained 3d (0.5mmol, 121mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4d (colorless oil, 4-methoxyphenethylsilane). The nuclear magnetic yield was 86%, and the isolated yield was 57%.

[0049] The chemical reaction formula of the above preparation process is:

[0050]

[0051] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.12(d,J=8.6Hz,2H),6.90–6.78(m,2H),3.80(s,3H), 3.51(t,J=3.8Hz,3H), 2.71(dd,J=9.2,7.2Hz,2H), 1.09(ddt,J=10.2,7.7,3.9Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ157.8,135.8,128.8,113.8,55.3,31.5,8.4. 29 SiNMR(79MHz,Chloroform-d)δ-59.13.HRMS(EI)m / z:[M+H] + calcdforC9H 15 OSi + :167.0887; found:167.0856.

[0052] Example 5

[0053] In a glove box filled with nitrogen, 4-fluorostyrene (denoted as 1e, 5 mmol, 596 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 shown in formula 3e. Then, in a glove box filled with nitrogen, the above-obtained 3e (0.5 mmol, 115 mg), HBpin (1.0 mmol, 145 μL) and BH3.THF (1.0 MinTHF, 10 mol%, 50 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70°C for 12 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as the eluent, the solvent was decompressed and dried to obtain a compound of formula 4e (colorless oil, 4-fluorophenethylsilane). The NMR yield was 87%, and the isolated yield was 55%.

[0054] The chemical reaction formula of the above preparation process is:

[0055]

[0056] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ7.15(dd,J=8.5,5.5Hz,2H),7.04–6.92(m,2H),3.51(t,J=3.8Hz,3H),2.82–2.66(m,2H),1.10(ddt,J=8.1,6.3,3.9Hz,2H). 13 CNMR (101MHz, Chloroform-d) δ 161.3 (d, J = 243.4Hz), 139.2 (d, J = 3.2Hz), 129.2 (d, J = 7.7Hz), 115.1 (d, J = 21.1Hz), 31.6. 29 SiNMR(79MHz,Chloroform-d)δ-59.07. 19 FNMR(376MHz,Chloroform-d)δ-111.18–-126.23(m).HRMS(EI)m / z:[M+H] + Calculate for C8H 12 F + :155.0687; found:155.0619.

[0057] Example 6

[0058] In a glove box filled with nitrogen, 4-chlorostyrene (denoted as 1f, 5mmol, 560μL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3f. Then, in a glove box filled with nitrogen, the above-obtained 3f (0.5mmol, 123mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4f (colorless oil, 4-chlorophenethylsilane). The nuclear magnetic yield was 75%, and the isolated yield was 47%.

[0059] The chemical reaction formula of the above preparation process is:

[0060]

[0061] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ7.24(d,J=8.4Hz,2H),7.11(d,J=8.3Hz,2H),3.50(t,J=3.8Hz,3H),2.77–2.62(m,2H),1.14–1.01(m,2H). 13 CNMR(101MHz,Chloroform-d)δ142.0,131.6,129.3,128.5,31.8,8.0. 29 SiNMR(79MHz,Chloroform-d)δ-58.93.HRMS(EI)m / z:[M+H] + calculation for C8H 12 C1S + :171.0391; found:172.0289.

[0062] Example 7

[0063] In a glove box filled with nitrogen, 4-bromostyrene (denoted as 1 g, 5 mmol, 654 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in Formula 3g. Then, in a glove box filled with nitrogen, the above-obtained 3g (0.5mmol, 145mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4g (colorless oil, 4-bromophenethylsilane). The nuclear magnetic yield was 68%, and the separation yield was 41%.

[0064] The chemical reaction formula of the above preparation process is:

[0065]

[0066] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ7.41(d,J=8.4Hz,2H),7.07(d,J=8.4Hz,2H),3.52(t,J=3.8Hz,3H),2.77–2.63(m,2H),1.09(ddt,J=8.1,6.3,3.8Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ142.6,131.5,129.7,119.6,31.8,8.0. 29 SiNMR(79MHz,Chloroform-d)δ-58.90.HRMS(EI)m / z:[M+H] + calculation for C8H 12 BnS + :214.9886; found:214.9813.

[0067] Example 8

[0068] In a glove box filled with nitrogen, 4-bromostyrene (denoted as 1h, 5mmol, 739μL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3h. Then, in a glove box filled with nitrogen, the above-obtained 3h (0.5mmol, 140mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4h (colorless oil, 4-trifluoromethylphenethylsilane). The nuclear magnetic yield was 57%, and the separation yield was 30%.

[0069] The chemical reaction formula of the above preparation process is:

[0070]

[0071] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ7.55(d,J=8.1Hz,2H),7.31(d,J=8.0Hz,2H),3.54(t,J=3.8Hz,3H),2.87–2.73(m,2H),1.13(ddt,J=10.0,7.7,3.9Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ147.7(d,J=1.2Hz),128.2,125.4(q,J=3.8Hz),32.3,7.9. 29 SiNMR(79MHz,Chloroform-d)δ-58.75. 19 F NMR(376MHz,Chloroform-d)δ-62.3.HRMS(EI)m / z:[M+H] + calcdforC9H 12 F3Si + :205.0655; found:205.0604.

[0072] Example 9

[0073] In a glove box filled with nitrogen, 2-vinylnaphthalene (denoted as 1i, 5 mmol, 695 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 shown in formula 3i. Then, in a glove box filled with nitrogen, the above-obtained 3i (0.5mmol, 131mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as the eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4i (colorless oil, 2-naphthylethylsilane). The nuclear magnetic yield was 82%, and the separation yield was 50%.

[0074] The chemical reaction formula of the above preparation process is:

[0075]

[0076] The characterization data are: 1 H NMR(400MHz,Chloroform-d)δ7.77(dd,J=11.6,9.0Hz,3H),7.60(s,1H),7.42(pd,J=6.9,1.5Hz,2H),7. 31(dd,J=8.4,1.7Hz,1H),3.53(t,J=3.8Hz,3H),3.00–2.73(m,2H),1.17(ddt,J=10.0,7.7,3.8Hz,2H). 13 C NMR (101MHz, Chloroform-d) δ141.2,133.7,132.1,128.1,127.7,127.6,127.0,126.0,125.8,125.3,32.6,8.1. 29 Si NMR(79MHz,Chloroform-d)δ-58.62.HRMS(EI)m / z:[M+H] + calcdforC 12 H 15 Si + :187.0938; found:187.0899.

[0077] Example 10

[0078] In a glove box filled with nitrogen, allylbenzene (denoted as 1j, 5 mmol, 662 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in formula 3j. Then, in a glove box filled with nitrogen, the above-obtained 3j (0.5mmol, 113mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4j (colorless oil, phenylpropylsilane). The nuclear magnetic yield was 88%, and the separation yield was 58%.

[0079] The chemical reaction formula of the above preparation process is:

[0080]

[0081] The characterization data are: 1 H NMR (400MHz, Chloroform-d) δ7.32–7.21(m,2H),7.18(t,J=7.7Hz,3H),3.50(t,J=3. 9Hz, 3H), 2.66 (t, J = 7.6Hz, 2H), 1.75 (p, J = 7.8Hz, 2H), 0.78 (dp, J = 11.7, 3.9Hz, 2H). 13 C NMR (101MHz, Chloroform-d) δ142.1,128.5,128.3,125.8,38.7,28.3,5.7. 29 Si NMR(79MHz,Chloroform-d)δ-58.86.HRMS(EI)m / z:[M+H] + calcdforC9H 15 Si + :151.0938; found:151.0888.

[0082] Embodiment 11

[0083] In a glove box filled with nitrogen, 4-phenyl-1-butene (denoted as 1k, 5 mmol, 751 μL), phenylsilane (denoted as 2a, 7.5 mmol, 925 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 shown in formula 3k. Then, in a glove box filled with nitrogen, the above-obtained 3k (0.5mmol, 120mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as the eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4k (colorless oil, phenylbutylsilane). The nuclear magnetic yield was 86%, and the separation yield was 56%.

[0084] The chemical reaction formula of the above preparation process is:

[0085]

[0086] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.26(q,J=7.5Hz,2H),7.21–7.10(m,3H),3.49(t,J=3.9Hz,3H),2 .69–2.51(m,2H),1.68(p,J=7.5Hz,2H),1.48(p,J=7.6Hz,2H),0.78(dp,J=11.6,4.4,3.9Hz,2H). 13 C NMR (101MHz, Chloroform-d) δ142.6,128.4,128.3,125.7,35.6,34.3,26.1,5.9. 29 Si NMR(79MHz,Chloroform-d)δ-59.00.HRMS(EI)m / z:[M+H] + Calculate for C 10 H 17 Si + :165.1094; found:165.1049.

[0087] Example 12

[0088] In a glove box filled with nitrogen, 1-dodecene (denoted as 1l, 5mmol, 1.1mL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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. Then, in a glove box filled with nitrogen, the above-obtained 3l (0.5mmol, 120mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4l (colorless oil, dodecylsilane). The nuclear magnetic yield was 80%, and the separation yield was 48%.

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

[0090]

[0091] The characterization data are: 1 H NMR (400MHz, Chloroform-d) δ3.48(t,J=3.9Hz,3H),1.43(dq,J=14.9,7.2,6.4Hz,2H),1.26(s,18H),0.88(t,J=6.8Hz,3H),0.74(dp,J=11.7,3.9Hz,2H). 13 C NMR (101MHz, Chloroform-d) δ32.5,32.0,29.7,29.6,29.5,29.4,29.3,26.4,22.7,14.1,5.9. 29 Si NMR(79MHz,Chloroform-d)δ-59.10.HRMS(EI)m / z:[M+H] + calcdforC 12 H 29 Si + :201.2033; found:201.1963.

[0092] Embodiment 13

[0093] In a glove box filled with nitrogen, 1-hexadecene (denoted as 1m, 5mmol, 1.4mL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3m. Then, in a glove box filled with nitrogen, the above-obtained 3m (0.5mmol, 166mg), HBpin (1.0mmol, 145μL) and BH3.THF (1.0MinTHF, 10mol%, 50μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 12h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4m (colorless oil, hexadecylsilane). The nuclear magnetic yield was 77%, and the separation yield was 45%.

[0094] The chemical reaction formula of the above preparation process is:

[0095]

[0096] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ3.48(t,J=3.9Hz,3H),1.48–1.38(m,2H),1.26(s,26H),0.88(t,J=6.8Hz,3H),0.75(dp,J=11.7,3.9Hz,2H). 13 CNMR(101MHz,Chloroform-d)δ32.5,32.0,29.7,29.6,29.4,29.3,26.4,22.7,14.1. 29 SiNMR(79MHz,Chloroform-d)δ-59.07.HRMS(EI)m / z:[M+H] + calcdforC 16 H 37 Si + :257.2659; found:257.2434.

[0097] Embodiment 14

[0098] In a glove box filled with nitrogen, 4-vinyl-4'-pentyldicyclohexane (denoted as 1n, 5mmol, 1.5mL), phenylsilane (denoted as 2a, 7.5mmol, 925μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3n. Then, in a glove box filled with nitrogen, the above-obtained 3n (0.5 mmol, 166 mg), HBpin (1.0 mmol, 145 μL) and BH3.THF (1.0 MinTHF, 10 mol%, 50 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70° C. for 12 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4n (colorless oil, 4'-pentyl-[1,1'-bis(cyclohexane)]-4-yl)ethyl)silane). The nuclear magnetic yield was 77%, and the isolated yield was 46%.

[0099] The chemical reaction formula of the above preparation process is:

[0100]

[0101] The characterization data are: 1 H NMR(400MHz,Chloroform-d)δ3.48(t,J=3.9Hz,3H),1.83–1.64(m,8H),1.36–1.19(m,9H),1.1 8–1.07(m,4H),1.02–0.94(m,5H),0.86(dt,J=19.1,9.1Hz,7H),0.74(dp,J=12.0,3.9Hz,2H). 13 C NMR (101MHz, Chloroform-d) δ43.5,40.3,37.5,34.0,33.7,33.2,32.3,30.2,30.0,26.7,22.8,14.1,3.3. 29 Si NMR(79MHz,Chloroform-d)δ-58.19.

[0102] Embodiment 15

[0103] In a glove box filled with nitrogen, 4-methylstyrene (denoted as 1b, 5 mmol, 659 μL), methylphenylsilane (denoted as 2b, 6 mmol, 824 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in formula 3o. Then, in a glove box filled with nitrogen, the above-obtained 3o (0.5 mmol, 120 mg), HBpin (0.65 mmol, 94 μL) and BH3.THF (1.0 Min THF, 20 mol%, 100 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70°C for 48 h. The obtained reaction solution was purified by silica gel column chromatography. After elution with n-pentane as the eluent, the solvent was decompressed and dried to obtain a compound of formula 4o (colorless oil, methyl (4-methylphenethyl) silane). The GC yield was 81% and the isolated yield was 63%.

[0104] The chemical reaction formula of the above preparation process is:

[0105]

[0106] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.11(s,4H),3.75(h,J=4.0Hz,2H),2.75–2.63(m,2H),2.33(s,3H),1.10–0.99(m,2H),0.15(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ141.2,135.2,129.0,127.8,30.9,21.0,12.7,-8.5. 29 SiNMR(79MHz,Chloroform-d)δ-33.31.HRMS(EI)m / z:[M+H] + calcdforC 10 H 17 Si + :165.1094; found:165.1055.

[0107] Example 16

[0108] In a glove box filled with nitrogen, 4-tert-butylstyrene (denoted as 1c, 5 mmol, 916 μL), methylphenylsilane (denoted as 2b, 6 mmol, 824 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 shown in formula 3p. Then, in a glove box filled with nitrogen, the above-obtained 3p (0.5mmol, 141mg), HBpin (0.65mmol, 94μL) and BH3.THF (1.0Min THF, 20mol%, 100μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 48h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4p (colorless oil, methyl (4-tert-butylphenylethyl) silane). The GC yield was 81%, and the isolated yield was 61%.

[0109] The chemical reaction formula of the above preparation process is:

[0110]

[0111] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.39–7.28(m,2H),7.16(d,J=8.4Hz,2H),3.77(h,J=4 .1Hz,2H),2.75–2.65(m,2H),1.33(s,9H),1.11–1.01(m,2H),0.16(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ148.6,127.5,125.3,34.4,31.5,30.7,12.5,-8.6. 29 SiNMR(79MHz,Chloroform-d)δ-33.85.HRMS(EI)m / z:[M+H] + calcdforC 13 H 23 Si+:207.1564; found:207.1534.

[0112] Embodiment 17

[0113] In a glove box filled with nitrogen, 4-fluorostyrene (denoted as 1e, 5 mmol, 596 μL), methylphenylsilane (denoted as 2b, 6 mmol, 824 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in formula 3q. Then, in a glove box filled with nitrogen, the above-obtained 3q (0.5 mmol, 122 mg), HBpin (0.65 mmol, 94 μL) and BH3.THF (1.0 Min THF, 20 mol%, 100 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70° C. for 48 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4q (colorless oil, methyl (4-fluorophenethyl) silane). The GC yield was 88%, and the isolated yield was 58%.

[0114] The chemical reaction formula of the above preparation process is:

[0115]

[0116] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.15(dd,J=8.3,5.6Hz,2H),6.96(t,J=8.7Hz,2H),3.73(h, J=3.8Hz,2H),2.74–2.64(m,2H),1.03(ddd,J=11.8,8.9,3.5Hz,2H),0.13(t,J=4.1Hz,3H). 13 CNMR (101MHz, Chloroform-d) δ162.4, 139.8 (d, J = 3.1Hz), 129.2 (d, J = 7.7Hz), 115.0 (d, J = 21.1Hz), 30.6, -8.6. 29 SiNMR(79MHz,Chloroform-d)δ-33.38. 19 FNMR(376MHz,Chloroform-d)δ-108.54–-124.58(m).HRMS(EI)m / z:[M+H] + Calcd for C9H 14 F + :169.0843; found:169.0796.

[0117] Embodiment 18

[0118] In a glove box filled with nitrogen, 4-chlorostyrene (denoted as 1f, 5 mmol, 599 μL), methylphenylsilane (denoted as 2b, 6 mmol, 824 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in formula 3r. Then, in a glove box filled with nitrogen, the above-obtained 3r (0.5 mmol, 130 mg), HBpin (0.65 mmol, 94 μL) and BH3.THF (1.0 Min THF, 20 mol%, 100 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70° C. for 48 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4r (colorless oil, methyl (4-chlorophenethyl) silane). The GC yield was 87%, and the isolated yield was 64%.

[0119] The chemical reaction formula of the above preparation process is:

[0120]

[0121] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.26–7.19(m,2H),7.12(d,J=8.4Hz,2H),3.73 (h,J=4.2Hz,2H),2.71–2.63(m,2H),1.05–0.96(m,2H),0.13(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ142.7,131.4,129.3,128.4,30.7,12.6,-8.6. 29 SiNMR(79MHz,Chloroform-d)δ-33.30.HRMS(EI)m / z:[M+H] + calcdforC9H 14 C1S + :185.0548; found:185.0457.

[0122] Embodiment 19

[0123] In a glove box filled with nitrogen, 4-trifluoromethylstyrene (denoted as 1h, 5mmol, 739μL), methylphenylsilane (denoted as 2b, 6mmol, 824μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 with the structure shown in formula 3s. Then, in a glove box filled with nitrogen, the above-obtained 3s (0.5 mmol, 147 mg), HBpin (0.65 mmol, 94 μL) and BH3.THF (1.0 Min THF, 20 mol%, 100 μL) were mixed in a 15 mL pressure tube with a magnetic element, and stirred at 70° C. for 48 h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4s (colorless oil, methyl (4-trifluoromethylphenethyl) silane). The GC yield was 81%, and the isolated yield was 57%.

[0124] The chemical reaction formula of the above preparation process is:

[0125]

[0126] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.54(d,J=8.1Hz,2H),7.31(d,J=8.0Hz,2H),3.7 6(h,J=4.0Hz,2H),2.81–2.73(m,2H),1.11–1.02(m,2H),0.16(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ148.3(d,J=1.2Hz),128.2,125.3(q,J=3.8Hz),31.2,12.4,-8.6. 29 SiNMR(79MHz,Chloroform-d)δ-33.15. 19 FNMR(376MHz,Chloroform-d)δ-62.26.HRMS(EI)m / z:[M+H] + calcdforC 10 H 14 F3Si + :219.0811; found:220.0730.

[0127] Embodiment 20

[0128] In a glove box filled with nitrogen, 2-vinylnaphthalene (denoted as 1i, 5mmol, 695μL), methylphenylsilane (denoted as 2b, 6mmol, 824μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3t. Then, in a glove box filled with nitrogen, the above-obtained 3t (0.5mmol, 138mg), HBpin (0.65mmol, 94μL) and BH3.THF (1.0Min THF, 20mol%, 100μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 48h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4t (colorless oil, methyl (4-trifluoromethylphenethyl) silane). The GC yield was 57%, and the isolated yield was 46%.

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

[0130]

[0131] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ7.86–7.76(m,3H),7.65(s,1H),7.45(pd,J=6.9,1.4Hz,2H),7.37(dd, J=8.4,1.6Hz,1H),3.80(h,J=4.0Hz,2H),2.94–2.86(m,2H),1.20–1.12(m,2H),0.18(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ141.8,133.7,132.0,127.9,127.6,127.5,127.0,125.9,125.7,125.1,31.5,12.5,-8.5. 29 SiNMR(79MHz,Chloroform-d)δ-33.36.HRMS(EI)m / z:[M+H] + calcdforC 13 H 17 Si + :201.1094; found:201.1052.

[0132] Embodiment 21

[0133] In a glove box filled with nitrogen, vinylferrocene (denoted as 1o, 5mmol, 1.0g), methylphenylsilane (denoted as 2b, 6mmol, 824μL) and Cp2ZrH2 (1mol%, 11.2mg) 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 shown in formula 3u. Then, in a glove box filled with nitrogen, the above-obtained 3u (0.5mmol, 167mg), HBpin (0.65mmol, 94μL) and BH3.THF (1.0Min THF, 20mol%, 100μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 48h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as an eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4u (colorless oil, methyl (ferrocenylethyl) silane). The GC yield was 38%, and the isolated yield was 29%.

[0134] The chemical reaction formula of the above preparation process is:

[0135]

[0136] The characterization data are: 1 HNMR (400MHz, Chloroform-d) δ4.13–4.04(m,9H),3.75(h,J=4.0Hz,2H),2.47–2.39(m,2H),0.96(ddd,J=11.9,6.2,3.6Hz,2H),0.16(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ91.6,67.8,67.2,25.1,12.2,-8.4. 29 SiNMR(79MHz,Chloroform-d)δ-33.08.HRMS(EI)m / z:[M+H] + calcdforC 13 H 19 FeSi + :259.0600; found:259.0562.

[0137] Embodiment 22

[0138] In a glove box filled with nitrogen, n-decene (denoted as 1p, 5 mmol, 947 μL), methylphenylsilane (denoted as 2b, 6 mmol, 824 μL) and Cp2ZrH2 (1 mol%, 11.2 mg) were mixed in a 15 mL pressure tube with a magnet and stirred at 100°C for 12 h. The resulting 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 with the structure shown in Formula 3v. Then, in a glove box filled with nitrogen, the above-obtained 3v (0.5mmol, 131mg), HBpin (0.65mmol, 94μL) and BH3.THF (1.0MinTHF, 20mol%, 100μL) were mixed in a 15mL pressure tube with a magnetic element, and stirred at 70°C for 48h. The obtained reaction solution was purified by silica gel column chromatography, and after elution with n-pentane as the eluent, the solvent was decompressed and dried to obtain a structural compound shown in formula 4v (colorless oil, decaalkylmethylsilane). The GC yield was 44% and the separation yield was 37%.

[0139] The chemical reaction formula of the above preparation process is:

[0140]

[0141] The characterization data are: 1 HNMR(400MHz,Chloroform-d)δ3.71(q,J=3.7Hz,2H),1.45–1.22(m,16H),0.89(t,J=6.7Hz,3H),0.68(tt,J=7.5,3.5Hz,2H),0.13(t,J=4.2Hz,3H). 13 CNMR(101MHz,Chloroform-d)δ32.9,32.0,29.7,29.6,29.4,25.2,22.7,10.5. 29 SiNMR(79MHz,Chloroform-d)δ-33.52.HRMS(EI)m / z:[M+H] + calcdforC 11 H 27 Si + :187.1877; found:187.1753.

[0142] The above is only a preferred embodiment of the present invention. It should be pointed out that for ordinary technicians in this technical field, several improvements and modifications can be made without departing from the principle of the present invention. These improvements and modifications should also be regarded as the scope of protection of the present invention.

Claims

1. A method for preparing alkyltrihydrosilane and methylalkyldihydrosilane, characterized in that: The method is to carry out a hydrosilation reaction of olefin compounds, silane compounds and Cp2ZrH2 catalyst at 100°C under a protective atmosphere, and then perform rapid column chromatography purification after 12 hours to obtain a secondary or tertiary silane compound. The obtained secondary or tertiary silane compound, a tetrahydrofuran solution of BH3 (1.0M) and pinacol borane are subjected to a silicon-boron functional group exchange reaction at 70°C, and after 12 to 48 hours of reaction, alkyl trihydrosilane and methyl alkyl dihydrosilane compounds are obtained.

2. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 1, characterized in that: The molar ratio of the olefin compound to the silane compound is 1:1.2-1.5, and the molar ratio of the secondary or tertiary silane obtained in the first step to the pinacol borane is 1:1.3-2.

3. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 1, characterized in that: The olefin compound has one of the following structural formulas: RCH=CH2, wherein R is one of an aryl group, an aromatic heterocycle or an alkyl group.

4. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 3, characterized in that: The R is one of 2-naphthalene, ferrocene, phenyl, substituted phenyl or alkyl.

5. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 4, characterized in that: The substituent in the substituted phenyl group is one of methyl, methoxy, fluorine, chlorine, bromine, tert-butyl and trifluoromethyl.

6. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 1, characterized in that: The silane compound is phenylsilane or methylphenylsilane.

7. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 1, characterized in that: The amount of the Cp2ZrH2 catalyst used is 1 mol%, and the amount of the BH3 tetrahydrofuran solution (1M) used is 10-20 mol%.

8. The method for preparing alkyltrihydrosilane and methylalkyldihydrosilane according to claim 1, characterized in that: The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

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