A method for preparing polysubstituted hydrosilane compounds

Abstract

The present invention relates to a method for preparing polysubstituted hydrosilane compounds. The method comprises conducting a silane recombination reaction at 60-100°C under a protective atmosphere with an aryl hydrosilane compound, an alkyl hydrosilane compound, and a tetrahydrofuran solution of borane dimethyl sulfide. The reaction is followed by rapid column chromatography purification after 24-48 hours to obtain the polysubstituted hydrosilane compounds. The method is simple to operate, low in cost, and applicable to a wide variety of aryl hydrosilane and alkyl hydrosilane substrates, with a wide range of functional group applicability. The polysubstituted hydrosilane compounds synthesized using the method of the present invention are diverse in variety, have good chemical selectivity, and facilitate product separation and purification.

Description

Technical Field

[0001] The present invention relates to the technical field of organic synthesis, and in particular to a method for preparing a multi-substituted hydrosilane compound. Background Art

[0002] Organosilanes are a rich and practical class of organic compounds. As important intermediates in synthetic chemistry, they are widely used in research fields such as materials science and the pharmaceutical industry. Due to their relative stability and broad reactivity, organosilanes are valuable compounds for a wide range of transformations and synthesis. In recent years, the synthesis and application of silicon-containing compounds, as highly useful synthetic intermediates, have garnered increasing attention from chemists.

[0003] Organosilicon compounds, due to their abundance, stability, and low toxicity, play an important role in synthetic chemistry. Common methods for synthesizing organosilicon compounds include hydrosilylation of olefins and coupling reactions of Grignard reagents with chlorosilanes. While these methods can be used to prepare hydrosilanes, functional group compatibility is limited, and efficient, broad-spectrum methods for synthesizing polysubstituted hydrosilanes remain lacking. Summary of the Invention

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

[0005] To solve the above problems, the present invention discloses a method for preparing a polysubstituted hydrogen silane compound, which is characterized in that: the method comprises carrying out a silane recombination reaction at 60-100°C under a protective atmosphere with an aryl hydrogen silane compound, an alkyl hydrogen silane compound, and a tetrahydrofuran solution of borane dimethyl sulfide, and then reacting for 24-48 hours and then performing rapid column chromatography purification to obtain a polysubstituted hydrogen silane compound.

[0006] The reaction equation is:

[0007]

[0008] The molar ratio of the arylhydrogensilane compound to the alkylhydrogensilane compound is 1:1.2-2.5.

[0009] The arylhydrosilane compound has one of the following structural formulas: ArSiMeH2 or ArSiMe2H, wherein: Ar is one of an aryl group and an aromatic heterocycle; or Ar is benzosilacyclobutane.

[0010] The Ar is one of N-methylindole, N-phenylcarbazole, 1-naphthalene, 2-naphthalene, 9-phenanthrene, 4-pyrene, 4-dibenzothiophene, phenyl, and substituted phenyl.

[0011] The substituent in the substituted phenyl group is one of methyl, 2,3-dimethyl, ethyl, isopropyl, methoxy, tert-butyl, phenyl, methylthio, N,N-dimethyl, morpholinyl, chlorine, cyclobutyl, adamantyl, benzyl ether, ether, trimethylsilyl, tert-butyl dimethyl ether, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, borate, and sulfonamide.

[0012] The alkylhydrogen silane compound has one of the following structural formulas: AlkylSiH3, AlkylSiMeH2, AlkylalkylSiH2 or Alkylalkyl 1 SiH2, where: Alkyl, alkyl, alkyl 1 It is a chain alkyl group or a cyclic alkyl group.

[0013] The concentration of the tetrahydrofuran solution of borane dimethyl sulfide is 2.0 mol / L; the amount of the tetrahydrofuran solution of borane dimethyl sulfide used is 10-20 mol% of the amount of the arylhydrosilane compound used.

[0014] The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

[0015] Compared with the prior art, the present invention has the following advantages:

[0016] 1. The present invention uses a tetrahydrofuran solution of cheap and readily available borane dimethyl sulfide as a catalyst, which greatly reduces production costs.

[0017] 2. The present invention does not use additives and can achieve the recombination reaction of arylhydrogensilane compounds and alkylhydrogensilane compounds with high chemical selectivity under relatively mild conditions to obtain a series of multi-substituted hydrosilane compounds. Therefore, it has certain guiding significance for enriching the synthesis methods of organosilicon compounds.

[0018] 3. The present invention is simple to operate, low in cost, applicable to various arylhydrosilane and alkylhydrosilane substrates, and has a wide range of functional group applicability.

[0019] 4. The polysubstituted hydrosilane 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

[0020] A method for preparing a polysubstituted hydrogen silane compound comprises the following steps: carrying out a silane recombination reaction at 60-100° C. on an aryl hydrogen silane compound, an alkyl hydrogen silane compound, and a tetrahydrofuran solution of borane dimethyl sulfide under a protective atmosphere; and performing rapid column chromatography purification after reacting for 24-48 hours to obtain the polysubstituted hydrogen silane compound.

[0021] Wherein, the molar ratio of the arylhydrogensilane compound to the alkylhydrogensilane compound is 1:1.2-2.5.

[0022] Arylhydrosilane compounds have one of the following structural formulas: ArSiMeH2 or ArSiMe2H, wherein Ar is an aryl group or an aromatic heterocycle; or Ar is benzosilacyclobutane. Ar is preferably N-methylindole, N-phenylcarbazole, 1-naphthalene, 2-naphthalene, 9-phenanthrene, 4-pyrene, 4-dibenzothiophene, phenyl, or a substituted phenyl group. The substituent in the substituted phenyl group is methyl, 2,3-dimethyl, ethyl, isopropyl, methoxy, tert-butyl, phenyl, methylthio, N,N-dimethyl, morpholino, chloro, cyclobutyl, adamantyl, benzyl ether, ether, trimethylsilyl, tert-butyldimethyl ether, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, borate, or sulfonamide. The substitution position of the substituent is not particularly limited.

[0023] The arylhydrogen silane compound can be selected from methylphenylsilane, methyl(4-methylphenyl)silane, methyl(4-methoxyphenyl)silane, methyl(4-tert-butylphenyl)silane, methyl(4-phenylphenyl)silane, methyl(4-methylthiophenyl)silane, methyl(4-N,N-dimethylaminophenyl)silane, methyl(4-morpholinophenyl)silane, methyl(4-chlorophenyl)silane, methyl(2-methylphenyl)silane, methyl(2-ethylphenyl)silane, methyl(2-isopropylphenyl)silane, methyl(2,3-dimethylphenyl)silane, methyl(cyclobutylphenyl)silane, methyl(N-methylindole)silane, methyl(N-phenylcarbazole)silane, methyl(1-naphthalene)silane, methyl One of (2-naphthyl)silane, methyl (9-phenanthrene)silane, methyl (4-pyrene)silane, dimethyl (4-adamantylphenyl)silane, dibenzo [b, d] thiophene-4-dimethylsilane, dimethyl (4-benzyl ether phenyl) silane, dimethyl (4-tert-butyldimethylsiloxyphenyl) silane, dimethyl (4-trimethylsilylphenyl) silane, dimethyl (4-difluoromethoxyphenyl) silane, dimethyl (4-trifluoromethoxyphenyl) silane, dimethyl (4-trifluoromethylthiophenyl) silane, dimethyl (4-pinacol borate phenyl) silane, dimethyl (4-sulfonamidophenyl) silane or 7,7-dimethyl-7-silabicyclo [4.2.0] octa-1,3,5-triene.

[0024] Alkylhydrogen silane compounds have one of the following structural formulas: AlkylSiH3, AlkylSiMeH2, AlkylalkylSiH2 or Alkylalkyl 1 SiH2, where: Alkyl, alkyl, alkyl 1 It is a chain alkyl group or a cyclic alkyl group.

[0025] The alkyl hydrogen silane compound can be selected from decylmethylsilane, n-octylsilane, n-hexylsilane, n-cyclohexylsilane, n-decylsilane, n-octadecylsilane, (2-(naphthalene-2-yl)ethyl)silane, diethylsilane, dicyclopentylsilane, di-n-pentylsilane, di-n-octylsilane, bis(2-ethylhexyl)silane, n-octylphenethylsilane, n-decylphenethylsilane, n-octyl(3-phenylpropyl)silane, n-pentyl-n-octylsilane, n-octyl(3-phenoxypropyl)silane, (5-(benzyloxy)pentyl)octylsilane, n-octyl(4-chlorobutyl)silane, n-octyl(5 bromopentyl)silane, octyl(5-(thien-2-yl)pentyl)silane, 1-(5-(octylsilyl)pentyl)-1H-pyrrole, 1-(5-(octylsilyl)pentyl)-1H-indole, 9-(5-(octylsilyl)pentyl)-9H-carbazole, N,4-dimethyl-N-(3-(octylsilyl)propyl)benzenesulfonamide, (5-cyclohexylpentyl)(octyl)silane, (5-cyclohexylpentyl)(octyl)silane, (5-cyclohexylpentyl)(octyl)silane, (5-cyclohexylpentyl)(octyl)silane, (5-cyclohexylpentyl)(octyl)silane, (5-cyclohexylpentyl)(octyl)silane.

[0026] The concentration of the tetrahydrofuran solution of borane dimethyl sulfide is 2.0 mol / L; the amount of the tetrahydrofuran solution of borane dimethyl sulfide used is 10-20 mol% of the amount of the arylhydrosilane compound used.

[0027] In the present invention, it is preferred to mix arylhydrosilane, alkylhydrosilane and BH3 . The SMe2 tetrahydrofuran solution was mixed in a pressure tube.

[0028] There is no particular limitation on the method of adding the alkali metal thereto in the present invention, and any method well known to those skilled in the art may be used.

[0029] 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.

[0030] In the present invention, the reaction is preferably carried out under stirring conditions, and there is no particular limitation on the stirring conditions. The reaction can be carried out using a process well known to those skilled in the art.

[0031] The present invention also preferably includes separation. Due to the low polarity of the resulting polysubstituted hydrosilane, rapid column chromatography using a low-polarity eluent is required for separation. Other separation processes are not particularly limited and can be performed using column chromatography and vacuum spin drying, processes well known to those skilled in the art.

[0032] In the present invention, unless otherwise specified, all raw materials are commercially available products well known to those skilled in the art.

[0033] Example 1

[0034] In a glove box filled with nitrogen, methylphenylsilane (denoted as 1a, 0.5 mmol, 61.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3a (a colorless oil, decylmethylphenylsilane). The isolated yield was 78%.

[0035] The chemical reaction formula of the above preparation process is:

[0036]

[0037] The characterization data are:

[0038] 1 H NMR (400 MHz, deuterated chloroform) δ 7.56–7.47 (m, 2H), 7.38–7.29 (m, 3H), 4.35 (h, J = 3.6 Hz, 1H), 1.41–1.19 (m, 16H), 0.91–0.75 (m, 5H), 0.32 (d, J = 3.7 Hz, 3H).

[0039] 13 C NMR (101 MHz, deuterated chloroform) δ 137.0, 134.5, 129.3, 128.0, 33.4, 32.1, 29.8, 29.7, 29.5, 24.5, 22.9, 14.3, 13.6, -5.5.

[0040] 29 Si NMR (79 MHz deuterated chloroform) δ-13.54.

[0041] Example 2

[0042] In a glove box filled with nitrogen, methyl (4-methylphenyl) silane (denoted as 1b, 0.5 mmol, 68.0 mg), decylmethyl silane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3b (a colorless oil, decylmethyl(4-methylphenyl)silane). The isolated yield was 87%.

[0043] The chemical reaction formula of the above preparation process is:

[0044]

[0045] The characterization data are:

[0046] 1 H NMR (400 MHz, deuterated chloroform) δ 7.42 (d, J = 7.8 Hz, 2H), 7.17 (d, J = 7.6 Hz, 2H), 4.32 (h, J = 3.6 Hz, 1H), 2.34 (s, 3H), 1.35–1.19 (m, 16H), 0.88 (t, J = 6.9 Hz, 3H), 0.79 (dqd, J = 14.8, 7.7, 3.4 Hz, 2H), 0.30 (d, J = 3.8 Hz, 3H).

[0047] 13 C NMR (101 MHz, deuterated chloroform) δ 139.1, 134.5, 133.2, 128.8, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.9, 21.6, 14.3, 13.7, -5.4.

[0048] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.88.

[0049] HRMS(ESI)m / z:[M+Na] + calcd for C 18 H 32 NaSi + :299.2165; found:299.2173.

[0050] Example 3

[0051] In a glove box filled with nitrogen, methyl(4-methoxyphenyl)silane (denoted as 1c, 0.5 mmol, 76.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3c (a colorless oil, decylmethyl(4-methoxyphenyl)silane). The isolated yield was 83%.

[0052] The chemical reaction formula of the above preparation process is:

[0053]

[0054] The characterization data are:

[0055] 1 H NMR (400 MHz, deuterated chloroform) δ 7.49–7.41 (m, 2H), 6.94–6.86 (m, 2H), 4.32 (h, J = 3.6 Hz, 1H), 3.80 (s, 3H), 1.39–1.22 (m, 16H), 0.91–0.71 (m, 5H), 0.30 (d, J = 3.8 Hz, 3H).

[0056] 13 C NMR (101 MHz, deuterated chloroform) δ 160.7, 127.7, 113.8, 55.1, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.9, 14.3, 13.5, -5.3.

[0057] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.17.

[0058] HRMS(ESI)m / z:[M+Na] + calcd for C 18 H 32 NaOSi + :315.2115; found:315.2119.

[0059] Example 4

[0060] In a nitrogen-filled glove box, methyl(4-tert-butylphenyl)silane (denoted as 1d, 0.5 mmol, 89.1 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3d (a colorless oil, decylmethyl(4-tert-butylphenyl)silane). The isolated yield was 71%.

[0061] The chemical reaction formula of the above preparation process is:

[0062]

[0063] The characterization data are:

[0064] 1 H NMR (400 MHz, deuterated chloroform) δ 7.57–7.50 (m, 2H), 7.49–7.40 (m, 2H), 4.40 (h, J = 3.6 Hz, 1H), 1.50–1.40 (m, 3H), 1.38 (s, 9H), 1.31 (s, 13H), 0.37 (d, J = 3.8 Hz, 3H).

[0065] 13 C NMR (101 MHz, deuterated chloroform) δ 152.2, 134.4, 133.4, 125.0, 34.8, 33.4, 32.1, 31.4, 29.8, 29.7, 29.54, 29.50, 24.6, 22.9, 14.3, 13.6, -5.4.

[0066] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.25.

[0067] HRMS(ESI)m / z:[M+Na] + calcd for C 21 H 38 NaSi + :341.2635; found:341.2636.

[0068] Example 5

[0069] In a glove box filled with nitrogen, methyl (4-phenylphenyl) silane (denoted as 1e, 0.5 mmol, 99.0 mg), decylmethyl silane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3e (a colorless oil, decylmethyl(4-phenylphenyl)silane). The isolated yield was 75%.

[0070] The chemical reaction formula of the above preparation process is:

[0071]

[0072] The characterization data are:

[0073] 1 H NMR (400 MHz, deuterated chloroform) δ 7.60 (dd, J = 5.0, 2.4 Hz, 6H), 7.44 (t, J = 7.6 Hz, 2H), 7.37–7.31 (m, 1H), 4.38 (h, J = 3.6 Hz, 1H), 1.42–1.22 (m, 16H), 0.94–0.78 (m, 5H), 0.36 (d, J = 3.8 Hz, 3H).

[0074] 13 C NMR (101 MHz, deuterated chloroform) δ 141.2, 135.7, 135.0, 128.9, 127.5, 127.3, 126.7, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.9, 14.3, 13.6, -5.4.

[0075] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.69.

[0076] Example 6

[0077] In a nitrogen-filled glove box, methyl(4-methylthiophenyl)silane (denoted as 1f, 0.5 mmol, 84.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3f (a colorless oil, decylmethyl(4-methylthiophenyl)silane). The isolated yield was 81%.

[0078] The chemical reaction formula of the above preparation process is:

[0079]

[0080] The characterization data are:

[0081] 1 H NMR (400 MHz, deuterated chloroform) δ 7.43 (d, J = 8.2 Hz, 2H), 7.23 (d, J = 8.2 Hz, 2H), 4.32 (h, J = 3.6 Hz, 1H), 2.47 (s, 3H), 1.39–1.22 (m, 16H), 0.88 (t, J = 6.9 Hz, 3H), 0.84–0.74 (m, 2H), 0.30 (d, J = 3.8 Hz, 3H).

[0082] 13 C NMR (101 MHz, deuterated chloroform) δ 140.0, 134.8, 132.8, 125.8, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.8, 15.5, 14.3, 13.6, -5.5.

[0083] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.76.

[0084] HRMS(ESI)m / z:[M+Na] + calcd for C 18 H 32 NaSSi + :331.1886; found:331.1892.

[0085] Example 7

[0086] In a glove box filled with nitrogen, methyl (4-N, N-dimethylphenyl) silane (denoted as 1 g, 0.5 mmol, 82.5 mg), decylmethyl silane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (40:1) as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3g (a purple-red oil, decylmethyl(4-N,N-dimethylphenyl)silane). The isolated yield was 73%.

[0087] The chemical reaction formula of the above preparation process is:

[0088]

[0089] The characterization data are:

[0090] 1 H NMR (400 MHz, deuterated chloroform) δ 7.32 (d, J = 8.6 Hz, 2H), 6.64 (d, J = 8.6 Hz, 2H), 4.23 (h, J = 3.5 Hz, 1H), 2.87 (s, 6H), 1.32–1.15 (m, 16H), 0.80 (t, J = 6.8 Hz, 3H), 0.76–0.64 (m, 2H), 0.20 (d, J = 3.7 Hz, 3H).

[0091] 13 C NMR (101 MHz, deuterated chloroform) δ 151.3, 135.5, 121.8, 112.1, 40.3, 33.4, 32.1, 29.8, 29.7, 29.5, 24.6, 22.9, 14.3, 14.0, -5.2.

[0092] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.70.

[0093] HRMS (APCI) m / z: [M+H] + calcd for C 19 H 36 NSi + :306.2612; found:306.2614.

[0094] Example 8

[0095] In a nitrogen-filled glove box, methyl(4-morpholinophenyl)silane (denoted as 1h, 0.5 mmol, 103.5 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as the eluent. The solvent was then removed by vacuum drying to afford the compound represented by Formula 3h (a brown oil, decylmethyl(4-morpholinophenyl)silane). The isolated yield was 74%.

[0096] The chemical reaction formula of the above preparation process is:

[0097]

[0098] The characterization data are:

[0099] 1 H NMR (400 MHz, deuterated chloroform) δ 7.43 (d, J = 8.5 Hz, 2H), 6.90 (d, J = 8.5 Hz, 2H), 4.31 (h, J = 3.5 Hz, 1H), 3.88–3.81 (m, 4H), 3.21–3.13 (m, 4H), 1.38–1.22 (m, 16H), 0.88 (t, J = 6.8 Hz, 1H), 0.84–0.72 (m, 2H), 0.29 (d, J = 3.7 Hz, 3H).

[0100] 13 C NMR (101 MHz, deuterated chloroform) δ 152.0, 135.6, 126.3, 67.0, 48.8, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.8, 14.3, 13.8, -5.3.

[0101] 29 Si NMR (79 MHz, deuterated chloroform) δ-4.82.

[0102] HRMS(ESI)m / z:[M+H] + calcd for C 21 H 38 NOSi + :348.2717; found:348.2715.

[0103] Example 9

[0104] In a glove box filled with nitrogen, methyl(4-chlorophenyl)silane (denoted as 1i, 0.5 mmol, 78.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 3i (a colorless oil, decylmethyl(4-chlorophenyl)silane). The isolated yield was 58%.

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

[0106]

[0107] The characterization data are:

[0108] 1H NMR (400 MHz, deuterated chloroform) δ 7.48–7.39 (m, 2H), 7.37–7.27 (m, 2H), 4.32 (h, J = 3.6 Hz, 1H), 1.35–1.22 (m, 16H), 0.88 (t, J = 6.9 Hz, 3H), 0.84–0.74 (m, 2H), 0.31 (d, J = 3.8 Hz, 3H).

[0109] 13 C NMR (101 MHz, deuterated chloroform) δ 135.8, 135.6, 135.2, 128.2, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.4, 22.9, 14.3, 13.5, -5.5.

[0110] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.36.

[0111] HRMS(ESI)m / z:[M+Na] + calcd for C 17 H 29 ClNaSi + :319.1619; found:319.1639.

[0112] Example 10

[0113] In a glove box filled with nitrogen, methyl(2-methylphenyl)silane (denoted as 1j, 0.5 mmol, 68.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3j (a colorless oil, decylmethyl(2-methylphenyl)silane). The isolated yield was 75%.

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

[0115]

[0116] The characterization data are:

[0117] 1H NMR (400 MHz, deuterated chloroform) δ 7.45 (dd, J = 7.6, 1.4 Hz, 1H), 7.30–7.22 (m, 1H), 7.20–7.10 (m, 2H), 4.44 (h, J = 3.7 Hz, 1H), 2.44 (s, 3H), 1.38–1.22 (m, 16H), 0.93–0.77 (m, 5H), 0.34 (d, J = 3.8 Hz, 3H).

[0118] 13 C NMR (101 MHz, deuterated chloroform) δ 143.9, 135.7, 135.1, 129.6, 125.1, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.8, 22.8, 22.6, 14.3, 13.4, -5.2.

[0119] 29 Si NMR (79 MHz, deuterated chloroform) δ-16.39.

[0120] Example 11

[0121] In a glove box filled with nitrogen, methyl(2-ethylphenyl)silane (denoted as 1k, 0.5 mmol, 75.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 3k (a colorless oil, decylmethyl(2-ethylphenyl)silane). The isolated yield was 65%.

[0122] The chemical reaction formula of the above preparation process is:

[0123]

[0124] The characterization data are:

[0125] 1 H NMR (400 MHz, deuterated chloroform) δ 7.29 (d, J = 7.2 Hz, 1H), 7.15 (t, J = 7.5 Hz, 1H), 7.08–6.95 (m, 2H), 4.31 (h, J = 3.6 Hz, 1H), 2.60 (q, J = 7.5 Hz, 2H), 1.21–1.05 (m, 19H), 0.76–0.60 (m, 5H), 0.18 (d, J = 3.8 Hz, 3H).

[0126] 13 C NMR (101 MHz, deuterated chloroform) δ 150.3, 135.2, 135.1, 129.7, 127.9, 125.2, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 29.2, 24.8, 22.9, 16.5, 14.3, 14.0, -4.6.

[0127] 29 Si NMR (79 MHz, deuterated chloroform) δ-17.12.

[0128] HRMS(ESI)m / z:[M+Na] + calcd for C 19 H 34 NaSi + :313.2322;found:313.2323.

[0129] Example 12

[0130] In a glove box filled with nitrogen, methyl(2-isopropylphenyl)silane (denoted as 11, 0.5 mmol, 82.1 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 31 (a colorless oil, decylmethyl(2-isopropylphenyl)silane). The isolated yield was 63%.

[0131] The chemical reaction formula of the above preparation process is:

[0132]

[0133] The characterization data are:

[0134] 1 H NMR (400 MHz, deuterated chloroform) δ 7.48–7.41 (m, 1H), 7.38–7.32 (m, 1H), 7.29 (d, J = 7.3 Hz, 1H), 7.15 (td, J = 7.3, 1.2 Hz, 1H), 4.47 (h, J = 3.6 Hz, 1H), 3.15 (hept, J = 6.8 Hz, 1H), 1.37–1.21 (m, 22H), 0.93–0.77 (m, 5H), 0.34 (d, J = 3.8 Hz, 3H).

[0135] 13C NMR (101 MHz, deuterated chloroform) δ 155.2, 135.3, 134.6, 129.9, 125.4, 124.9, 33.8, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.9, 24.7, 24.6, 22.9, 14.3, -4.4.

[0136] 29 Si NMR (79 MHz, deuterated chloroform) δ-16.32.

[0137] HRMS(ESI)m / z:[M+H] + calcd for C 20 H 37 Si + :305.2659; found:305.2647.

[0138] Example 13

[0139] In a glove box filled with nitrogen, methyl(2,3-dimethylphenyl)silane (denoted as 1m, 0.5mmol, 75.0mg), decylmethylsilane (denoted as 2a, 1.0mmol, 186.2mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 3m (a colorless oil, decylmethyl(2,3-dimethylphenyl)silane). The isolated yield was 66%.

[0140] The chemical reaction formula of the above preparation process is:

[0141]

[0142] The characterization data are:

[0143] 1 H NMR (400 MHz, deuterated chloroform) δ 7.32 (d, J = 7.2 Hz, 1H), 7.17 (d, J = 7.2 Hz, 1H), 7.09 (t, J = 7.4 Hz, 1H), 4.46 (h, J = 3.7 Hz, 1H), 2.36 (s, 3H), 2.27 (s, 3H), 1.38–1.22 (m, 16H), 0.94–0.77 (m, 5H), 0.34 (d, J = 3.8 Hz, 3H).

[0144] 13C NMR (101 MHz, deuterated chloroform) δ 142.3, 136.4, 133.0, 131.3, 125.3, 33.4, 32.1, 29.8, 29.7, 29.5, 29.5, 22.9, 20.6, 19.6, 14.3, 13.8, -4.8.

[0145] 29 Si NMR (79 MHz, deuterated chloroform) δ-15.66.

[0146] Example 14

[0147] In a glove box filled with nitrogen, bicyclo[4.2.0]octyl-1(6),2,4-trien-3-yl(methyl)silane (denoted as 1n, 0.5mmol, 73.5mg), decylmethylsilane (denoted as 2a, 1.0mmol, 186.2mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3n (a colorless oil, bicyclo[4.2.0]octyl-1(6),2,4-trien-3-yl(decyl)(methyl)silane). The isolated yield was 83%.

[0148] The chemical reaction formula of the above preparation process is:

[0149]

[0150] The characterization data are:

[0151] 1 H NMR (400 MHz, deuterated chloroform) δ 7.37 (d, J = 7.2 Hz, 1H), 7.21 (d, J = 3.7 Hz, 1H), 7.05 (d, J = 7.2 Hz, 1H), 4.32 (h, J = 3.6 Hz, 1H), 3.18 (s, 4H), 1.37–1.21 (m, 16H), 0.88 (t, J = 6.9 Hz, 3H), 0.94–0.73 (m, 2H), 0.30 (d, J = 3.8 Hz, 3H).

[0152] 13 C NMR (101 MHz, deuterated chloroform) δ 147.3, 145.7, 134.8, 132.7, 128.1, 122.0, 33.3, 32.0, 30.0, 29.8, 29.7, 29.6, 29.4, 29.3, 24.4, 22.8, 14.2, 13.7, -5.3.

[0153] 29 Si NMR (79 MHz, deuterated chloroform) δ-12.70.

[0154] HRMS(ESI)m / z:[M+H] + calcd for C 19 H 33 Si + :289.2346; found:289.2349.

[0155] Example 15

[0156] In a glove box filled with nitrogen, (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methylsilane (denoted as 1o, 0.5 mmol, 90.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3o (a colorless oil, decyl(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(methyl)silane). The isolated yield was 67%.

[0157] The chemical reaction formula of the above preparation process is:

[0158]

[0159] The characterization data are:

[0160] 1 H NMR (400 MHz, deuterated chloroform) δ 7.04–6.93 (m, 2H), 6.86 (d, J = 7.9 Hz, 1H), 4.29 (h, J = 3.6 Hz, 1H), 4.23 (s, 4H), 1.42–1.19 (m, 16H), 0.88 (t, J = 6.9 Hz, 3H), 0.82–0.72 (m, 2H), 0.28 (d, J = 3.8 Hz, 3H).

[0161] 13 C NMR (101 MHz, deuterated chloroform) δ 144.7, 143.5, 129.2, 127.6, 123.1, 117.3, 64.6, 64.4, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.8, 14.3, 13.7, -5.4.

[0162] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.87.

[0163] HRMS (APCI) m / z: [M+H] + calcd for C 19 H 33 O2Si + :321.2244; found:321.2234.

[0164] Example 16

[0165] In a nitrogen-filled glove box, benzo[d][1,3]dioxy-5-yl(methyl)silane (denoted as 1p, 0.5 mmol, 83.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 3p (a colorless oil, benzo[d][1,3]dioxy-5-yl(decyl)(methyl)silane). The isolated yield was 69%.

[0166] The chemical reaction formula of the above preparation process is:

[0167]

[0168] The characterization data are:

[0169] 1 H NMR (400 MHz, deuterated chloroform) δ 7.04–6.99 (m, 1H), 6.97 (s, 1H), 6.84 (d, J = 7.6 Hz, 1H), 5.93 (s, 2H), 4.30 (h, J = 3.6 Hz, 1H), 1.42–1.17 (m, 16H), 0.88 (t, J = 6.8 Hz, 3H), 0.77 (m, 2H), 0.29 (d, J = 3.8 Hz, 3H).

[0170] 13 C NMR (101 MHz, deuterated chloroform) δ 148.7, 147.5, 129.8, 128.4, 113.7, 108.8, 100.7, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.4, 22.8, 14.3, 13.8, -5.2.

[0171] 29 Si NMR (79 MHz, deuterated chloroform) δ-12.91.

[0172] HRMS(ESI)m / z:[M+H] + calcd for C 18 H 31 O2Si + :307.2088; found:307.2086.

[0173] Example 17

[0174] In a nitrogen-filled glove box, (2,2-difluorobenzo[d][1,3]dioxy-5-yl)(methyl)silane (denoted as 1q, 0.5 mmol, 101.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3q (a colorless oil, decyl(2,2-difluorobenzo[d][1,3]dioxy-5-yl)(methyl)silane). The isolated yield was 27%.

[0175] The chemical reaction formula of the above preparation process is:

[0176]

[0177] The characterization data are:

[0178] 1 H NMR (400 MHz, deuterated chloroform) δ 7.26–7.20 (m, 1H), 7.18 (s, 1H), 7.05 (d, J = 7.8 Hz, 1H), 4.34 (h, J = 3.5 Hz, 1H), 1.29 (d, J = 32.6 Hz, 16H), 0.88 (t, J = 6.8 Hz, 3H), 0.84–0.76 (m, 2H), 0.32 (d, J = 3.8 Hz, 3H).

[0179] 13 C NMR (101 MHz, deuterated chloroform) δ 144.77, 143.96, 132.87, 131.51 (d, J = 255.8 Hz), 123.0, 114.6, 109.5, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.3, 22.8, 14.3, 13.6, -5.3.

[0180] 29 Si NMR (79 MHz, deuterated chloroform) δ-12.03.

[0181] 19 F NMR (377 MHz, deuterated chloroform) δ-50.16.

[0182] Example 18

[0183] In a glove box filled with nitrogen, methyl(N-methyl-4-indolyl)silane (denoted as 1r, 0.5 mmol, 87.5 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3r (a pale yellow oil, decylmethyl(N-methyl-4-indolyl)silane). The isolated yield was 29%.

[0184] The chemical reaction formula of the above preparation process is:

[0185]

[0186] The characterization data are:

[0187] 1 H NMR (400 MHz, deuterated chloroform) δ 7.30–7.18 (m, 2H), 7.17–7.08 (m, 1H), 7.04–6.91 (m, 1H), 6.52 (s, 1H), 4.57–4.47 (m, 1H), 3.68 (s, 3H), 1.36–1.13 (m, 17H), 0.95–0.69 (m, 5H), 0.34 (m, 3H).

[0188] 13 C NMR (101 MHz, deuterated chloroform) δ 135.5, 133.0, 128.9, 126.3, 121.2, 110.6, 101.8, 33.4, 32.9, 32.1, 29.8, 29.7, 29.5, 29.4, 24.8, 22.9, 14.3, 13.7, -5.2.

[0189] 29 Si NMR (79 MHz, deuterated chloroform) δ-16.53.

[0190] HRMS(ESI)m / z:[M+Na]+ calcd for C 20 H 33 NNaSi + :338.2274; found:338.2265.

[0191] Example 19

[0192] In a nitrogen-filled glove box, methyl(4-N-carbazolylphenyl)silane (denoted as 1s, 0.5 mmol, 143.5 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3s (a colorless oil, decylmethyl(4-N-carbazophenyl)silane). The isolated yield was 67%.

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

[0194]

[0195] The characterization data are:

[0196] 1 H NMR (400 MHz, deuterated chloroform) δ 8.12 (d, J = 7.7 Hz, 2H), 7.79–7.66 (m, 2H), 7.57–7.49 (m, 2H), 7.47–7.32 (m, 4H), 7.31–7.19 (m, 2H), 4.44 (dq, J = 7.2, 3.7 Hz, 1H), 1.47–1.23 (m, 16H), 1.00–0.82 (m, 5H), 0.40 (d, J = 3.6 Hz, 3H).

[0197] 13 C NMR (101 MHz, deuterated chloroform) δ 140.9, 136.3, 136.0, 126.4, 126.1, 123.6, 120.4, 120.1, 110.0 33.4, 32.1, 29.8, 29.7, 29.5, 24.5, 22.9, 14.3, 13.5, -5.4.

[0198] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.38.

[0199] HRMS(ESI)m / z:[M+Na] +calcd for C 29 H 37 NNaSi + :450.2587; found:450.2582.

[0200] Example 20

[0201] In a glove box filled with nitrogen, methyl(1-naphthyl)silane (denoted as 1t, 0.5 mmol, 86.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3t (a colorless oil, decylmethyl(1-naphthyl)silane). The isolated yield was 68%.

[0202] The chemical reaction formula of the above preparation process is:

[0203]

[0204] The characterization data are:

[0205] 1 H NMR (400 MHz, deuterated chloroform) δ 8.11 (d, J = 8.0 Hz, 1H), 7.89–7.77 (m, 2H), 7.71 (dd, J = 6.7, 1.1 Hz, 1H), 7.54–7.36 (m, 3H), 4.78 (h, J = 3.7 Hz, 1H), 1.35–1.19 (m, 16H), 0.98 (m, 2H), 0.87 (t, J = 6.9 Hz, 3H), 0.46 (d, J = 3.8 Hz, 3H).

[0206] 13 C NMR (101 MHz, deuterated chloroform) δ 138.3, 136.3, 135.2, 134.4, 131.1, 130.1, 128.9, 127.0, 126.6, 126.3, 34.3, 33.1, 30.8, 30.7, 30.5, 30.4, 25.9, 23.9, 15.3, 14.9, -3.8.

[0207] 29 Si NMR (79 MHz, deuterated chloroform) δ-15.63.

[0208] HRMS(ESI)m / z:[M+Na] +calcd for C 21 H 32 NaSi + :335.2165; found:335.2168.

[0209] Example 21

[0210] In a nitrogen-filled glove box, methyl(2-naphthyl)silane (denoted as 1u, 0.5mmol, 86.0mg), decylmethylsilane (denoted as 2a, 1.0mmol, 186.2mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3u (a colorless oil, decylmethyl(2-naphthyl)silane). The isolated yield was 84%.

[0211] The chemical reaction formula of the above preparation process is:

[0212]

[0213] The characterization data are:

[0214] 1 H NMR (400 MHz, deuterated chloroform) δ 8.03 (s, 1H), 7.86–7.75 (m, 3H), 7.58 (dd, J = 8.1, 1.0 Hz, 1H), 7.50–7.42 (m, 2H), 4.47 (h, J = 3.6 Hz, 1H), 1.40–1.19 (m, 16H), 0.98–0.82 (m, 5H), 0.40 (d, J = 3.8 Hz, 3H).

[0215] 13 C NMR (101 MHz, deuterated chloroform) δ 135.2, 134.4, 134.0, 133.1, 130.6, 128.1, 127.9, 127.2, 126.5, 126.1, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.9, 14.3, 13.6, -5.4.

[0216] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.05.

[0217] Example 22

[0218] In a glove box filled with nitrogen, methyl(phenanthren-9-yl)silane (denoted as 1v, 0.5mmol, 111.0mg), decylmethylsilane (denoted as 2a, 1.0mmol, 186.2mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3v (a colorless oil, decylmethyl(phenanthren-9-yl)silane). The isolated yield was 65%.

[0219] The chemical reaction formula of the above preparation process is:

[0220]

[0221] The characterization data are:

[0222] 1 H NMR (400 MHz, deuterated chloroform) δ 8.72–8.66 (m, 1H), 8.63 (d, J = 8.2 Hz, 1H), 8.17–8.09 (m, 1H), 7.99 (s, 1H), 7.85 (d, J = 7.5 Hz, 1H), 7.66–7.52 (m, 4H), 4.80 (h, J = 3.5 Hz, 1H), 1.43 (dt, J = 15.4, 7.4 Hz, 2H), 1.36–1.17 (m, 14H), 1.11–0.95 (m, 2H), 0.86 (t, J = 6.9 Hz, 3H), 0.52 (d, J = 3.8 Hz, 3H).

[0223] 13 C NMR (101 MHz, deuterated chloroform) δ 136.4, 135.2, 133.9, 131.3, 130.1, 128.9, 128.6, 127.3, 126.7, 126.6, 126.3, 123.3, 122.6, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.9, 22.9, 14.3, 13.8, -4.8.

[0224] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.31.

[0225] HRMS(ESI)m / z:[M+Na] + calcd for C 25 H 34 NaSi +:385.2322; found:385.2326.

[0226] Example 23

[0227] In a glove box filled with nitrogen, methyl(pyrene-4-yl)silane (denoted as 1w, 0.5 mmol, 124.0 mg), decylmethylsilane (denoted as 2a, 1.0 mmol, 186.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 80°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3w (a colorless oil, decylmethyl(4-pyrenyl)silane). The isolated yield was 29%.

[0228] The chemical reaction formula of the above preparation process is:

[0229]

[0230] The characterization data are:

[0231] 1 H NMR (400 MHz, deuterated chloroform) δ 8.38 (d, J = 9.1 Hz, 1H), 8.23–8.08 (m, 5H), 8.08–7.93 (m, 3H), 4.99 (h, J = 3.3 Hz, 1H), 1.44 (p, J = 7.3 Hz, 2H), 1.36–1.28 (m, 2H), 1.26–1.01 (m, 14H), 0.85 (t, J = 6.9 Hz, 3H), 0.58 (d, J = 3.8 Hz, 3H).

[0232] 13 C NMR (101 MHz, deuterated chloroform) δ 136.0, 132.9, 132.6, 132.4, 131.4, 130.9, 128.1, 127.7, 127.5, 127.40, 125.9, 125.3, 124.3, 33.3, 32.0, 29.8, 29.7, 29.5, 29.4, 24.9, 22.8, 14.2, -4.5.

[0233] 29 Si NMR (79 MHz, deuterated chloroform) δ-15.58.

[0234] Example 24

[0235] In a nitrogen-filled glove box, dimethyl(4-adamantylphenyl)silane (denoted as 1x, 0.5 mmol, 135.1 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3x (a colorless oil, decylmethyl(4-adamantylphenyl)silane). The isolated yield was 38%.

[0236] The chemical reaction formula of the above preparation process is:

[0237]

[0238] The characterization data are:

[0239] 1 H NMR (400 MHz, deuterated chloroform) δ 7.49 (d, J = 8.1 Hz, 2H), 7.35 (d, J = 8.1 Hz, 2H), 4.33 (h, J = 3.3 Hz, 1H), 2.09 (s, 3H), 1.92 (s, 6H), 1.83–1.71 (m, 6H), 1.47–1.14 (m, 16H), 0.92–0.73 (m, 5H), 0.31 (d, J = 3.8 Hz, 3H).

[0240] 13 C NMR (101 MHz, deuterated chloroform) δ 152.5, 134.4, 133.4, 124.5, 43.2, 37.0, 36.4, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 29.1, 24.6, 22.9, 14.3, 13.6, -5.5.

[0241] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.31.

[0242] HRMS(ESI)m / z:[M+Na] + calcd for C 27 H 44 NaSi + :419.3104; found:419.3107.

[0243] Example 25

[0244] In a nitrogen-filled glove box, dimethyl(2-dibenzothienyl)silane (denoted as 1y, 0.5 mmol, 121.0 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3y (a colorless oil, decylmethyl(2-dibenzothienyl)silane). The isolated yield was 52%.

[0245] The chemical reaction formula of the above preparation process is:

[0246]

[0247] The characterization data are:

[0248] 1 H NMR (400 MHz, deuterated chloroform) δ 8.20–8.05 (m, 2H), 7.84 (dd, J = 6.1, 2.7 Hz, 1H), 7.59 (dd, J = 7.0, 1.0 Hz, 1H), 7.48–7.35 (m, 3H), 4.66 (h, J = 3.6 Hz, 1H), 1.41 (p, J = 8.1 Hz, 2H), 1.36–1.13 (m, 14H), 1.00 (dtdt, J = 19.2, 11.2, 7.5, 4.3 Hz, 2H), 0.86 (t, J = 6.9 Hz, 3H), 0.47 (d, J = 3.8 Hz, 3H).

[0249] 13 C NMR (101 MHz, deuterated chloroform) δ 139.6, 135.6, 134.8, 133.3, 131.1, 126.7, 124.4, 124.0, 122.8, 122.7, 121.7, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.6, 22.8, 14.3, 12.9, -5.8.

[0250] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.92.

[0251] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 32 NaSSi +:391.1886; found:391.1888.

[0252] Example 26

[0253] In a glove box filled with nitrogen, dimethyl(4-benzyloxyphenyl)silane (denoted as 1z, 0.5 mmol, 121.0 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3z (a colorless oil, decylmethyl(4-benzyloxyphenyl)silane). The isolated yield was 71%.

[0254] The chemical reaction formula of the above preparation process is:

[0255]

[0256] The characterization data are:

[0257] 1 H NMR (400 MHz, deuterated chloroform) δ 7.43 (dd, J = 13.8, 7.9 Hz, 4H), 7.36 (t, J = 7.4 Hz, 2H), 7.29 (t, J = 7.1 Hz, 1H), 6.97 (d, J = 8.3 Hz, 2H), 5.04 (s, 2H), 4.33 (h, J = 3.4 Hz, 1H), 1.42–1.18 (m, 16H), 0.88 (t, J = 6.8 Hz, 3H), 0.84–0.73 (m, 2H), 0.29 (d, J = 3.7 Hz, 3H).

[0258] 13 C NMR (101 MHz, deuterated chloroform) δ 159.9, 137.1, 135.9, 128.7, 128.1, 128.0, 127.6, 114.6, 69.8, 33.4, 32.1, 29.8, 29.7, 29.5, 29.4, 24.5, 22.9, 13.8, -5.3.

[0259] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.13.

[0260] HRMS(ESI)m / z:[M+Na] + calcd for C 24 H 36 NaOSi+ :391.2428; found:391.2425.

[0261] Example 27

[0262] In a glove box filled with nitrogen, (4-methoxy-3-(3-methoxypropyloxy)phenyl)dimethylsilane (denoted as 1aa, 0.5mmol, 127.1mg), decylmethylsilane (denoted as 2a, 0.6mmol, 111.6mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (10:1) as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3aa (a colorless oil, decyl(4-methyloxy-3-(3-methoxypropoxy)phenyl)methylsilane). The isolated yield was 75%.

[0263] The chemical reaction formula of the above preparation process is:

[0264]

[0265] The characterization data are:

[0266] 1 H NMR (400 MHz, deuterated chloroform) δ 7.08 (d, J = 7.8 Hz, 1H), 7.05 (s, 1H), 6.88 (d, J = 7.8 Hz, 1H), 4.32 (h, J = 3.3 Hz, 1H), 4.14 (t, J = 6.5 Hz, 2H), 3.86 (s, 3H), 3.58 (t, J = 6.1 Hz, 2H), 3.35 (s, 3H), 2.11 (p, J = 6.3 Hz, 2H), 1.44–1.17 (m, 16H), 0.88 (t, J = 6.8 Hz, 3H), 0.79 (dtt, J = 15.0, 7.9, 3.8 Hz, 2H), 0.30 (d, J = 3.8 Hz, 3H).

[0267] 13 C NMR (101 MHz, deuterated chloroform) δ 150.6, 148.2, 128.1, 127.7, 118.9, 111.6, 69.4, 66.2, 58.8, 55.8, 33.3, 32.0, 29.8, 29.7, 29.6, 29.5, 29.4, 24.5, 22.8, 14.2, 13.7, -5.3.

[0268] 29Si NMR (79 MHz, deuterated chloroform) δ-13.56.

[0269] HRMS(ESI)m / z:[M+Na] + calcd for C 22 H 40 NaO3Si + :403.2639; found:403.2636.

[0270] Example 28

[0271] In a nitrogen-filled glove box, (4-((((1S,2R,5S)-2-isopropyl-5-methyl)cyclohexyloxy)methylphenyl)dimethylsilane (denoted as 1ab, 0.5 mmol, 152.1 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate = 30:1 as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3ab (a colorless oil, decyl(4-((((1S,2R,5S)-2-isopropyl-5-methyl)cyclohexyloxy)methylphenyl)dimethylsilane). The isolated yield was 78%.

[0272] The chemical reaction formula of the above preparation process is:

[0273]

[0274] Example 29

[0275] In a nitrogen-filled glove box, dimethyl(4-tert-butyldimethylsilyloxyphenyl)silane (denoted as 1ac, 0.5 mmol, 133.1 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 3ac (a colorless oil, decylmethyl(4-tert-butyldimethylsilyloxyphenyl)silane). The isolated yield was 82%.

[0276] The chemical reaction formula of the above preparation process is:

[0277]

[0278] The characterization data are:

[0279] 1 H NMR (400 MHz, deuterated chloroform) δ 7.44 (d, J = 8.4 Hz, 2H), 6.89 (d, J = 8.3 Hz, 2H), 4.38 (h, J = 3.5 Hz, 1H), 1.49–1.22 (m, 16H), 1.04 (s, 9H), 0.94 (t, J = 6.8 Hz, 3H), 0.88–0.78 (m, 2H), 0.35 (d, J = 3.8 Hz, 3H), 0.26 (s, 6H).

[0280] 13 C NMR (101 MHz, deuterated chloroform) δ 156.9, 135.8, 128.4, 119.9, 33.4, 32.1, 29.9, 29.8, 29.6, 29.5, 25.9, 24.5, 22.9, 18.4, 14.3, 13.8, -4.2, -5.3.

[0281] 29 Si NMR (79 MHz, deuterated chloroform) δ 20.58, -14.18.

[0282] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 44 NaOSi2 + :415.2823; found:415.2820.

[0283] Example 30

[0284] In a nitrogen-filled glove box, dimethyl(4-trimethylsilylphenyl)silane (denoted as 1ad, 0.5 mmol, 104.1 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent, and the solvent was evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3ad (a colorless oil, decylmethyl(4-trimethylsilylphenyl)silane). The isolated yield was 75%.

[0285] The chemical reaction formula of the above preparation process is:

[0286]

[0287] The characterization data are:

[0288] 1 H NMR (400 MHz, deuterated chloroform) δ 7.58 (s, 4H), 4.40 (h, J = 3.6 Hz, 1H), 1.47–1.30 (m, 16H), 0.97–0.82 (m, 5H), 0.38 (d, J = 3.8 Hz, 3H), 0.33 (s, 9H).

[0289] 13 C NMR (101 MHz, deuterated chloroform) δ 141.6, 137.5, 133.8, 132.8, 33.4, 32.1, 29.8, 29.7, 29.6, 29.5, 24.5, 22.9, 14.3, 13.5, -1.0, -5.5.

[0290] 29 Si NMR (79 MHz, deuterated chloroform) δ -4.07, -13.72.

[0291] HRMS(ESI)m / z:[M+Na] + calcd for C 20 H 38 NaSi2 + :357.2404; found:357.2401.

[0292] Example 31

[0293] In a glove box filled with nitrogen, dimethyl(4-difluoromethoxyphenyl)silane (denoted as 1ae, 0.5 mmol, 101.0 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3ae (a colorless oil, decylmethyl(4-difluoromethoxyphenyl)silane). The isolated yield was 51%.

[0294] The chemical reaction formula of the above preparation process is:

[0295]

[0296] The characterization data are:

[0297] 1H NMR (400 MHz, deuterated chloroform) δ 7.52 (d, J = 8.4 Hz, 2H), 7.09 (d, J = 8.3 Hz, 2H), 6.51 (t, J = 74.0 Hz, 1H), 4.34 (h, J = 3.6 Hz, 1H), 1.44–1.14 (m, 16H), 0.92–0.74 (m, 5H), 0.32 (d, J = 3.8 Hz, 3H).

[0298] 13 C NMR (101 MHz, deuterated chloroform) δ 136.1, 133.9, 118.9, 116.0 (t, J = 259.3 Hz), 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.4, 22.9, 14.3, 13.5, -5.5.

[0299] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.57.

[0300] 19 F NMR (377 MHz, deuterated chloroform) δ -80.58, -80.78.

[0301] Example 32

[0302] In a nitrogen-filled glove box, dimethyl(4-trifluoromethoxyphenyl)silane (denoted as 1af, 0.5 mmol, 110.0 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3af (a colorless oil, decylmethyl(4-trifluoromethoxyphenyl)silane). The isolated yield was 41%.

[0303] The chemical reaction formula of the above preparation process is:

[0304]

[0305] The characterization data are:

[0306] 1H NMR (400 MHz, deuterated chloroform) δ 7.60–7.48 (m, 2H), 7.19 (d, J = 7.7 Hz, 2H), 4.35 (h, J = 3.6 Hz, 1H), 1.37–1.24 (m, 16H), 0.90–0.75 (m, 5H), 0.33 (d, J = 3.8 Hz, 3H).

[0307] 13 C NMR (101 MHz, deuterated chloroform) δ 150.4, 136.0, 135.7, 120.7 (d, J = 258.6 Hz), 120.3, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.4, 22.9, 14.3, 13.5, -5.5.

[0308] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.41.

[0309] 19 F NMR (377 MHz, deuterated chloroform) δ-57.67.

[0310] Example 33

[0311] In a glove box filled with nitrogen, dimethyl(4-trifluoromethylthiophenyl)silane (denoted as 1ag, 0.5mmol, 118.0mg), decylmethylsilane (denoted as 2a, 0.6mmol, 111.6mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 3ag (a colorless oil, decylmethyl(4-trifluoromethylthiophenyl)silane). The isolated yield was 44%.

[0312] The chemical reaction formula of the above preparation process is:

[0313]

[0314] The characterization data are:

[0315] 1 H NMR (400 MHz, deuterated chloroform) δ 7.46 (d, J = 7.9 Hz, 2H), 7.41 (d, J = 8.1 Hz, 2H), 4.19 (m, 1H), 1.26–1.08 (m, 16H), 0.74–0.61 (m, 5H), 0.18 (d, J = 3.8 Hz, 3H).

[0316] 13 C NMR (101 MHz, deuterated chloroform) δ 140.8, 135.4, 131.3, 128.3, 125.4 (q, J = 1.8 Hz), 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 24.4, 22.9, 14.3, 13.3, -5.7.

[0317] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.04.

[0318] 19 F NMR (377 MHz, deuterated chloroform) δ-42.47.

[0319] Example 34

[0320] In a glove box filled with nitrogen, dimethyl(4-(1,2,2-triphenylvinyl)phenyl)silane (denoted as 1ah, 0.5mmol, 195.1mg), decylmethylsilane (denoted as 2a, 0.6mmol, 111.6mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (50:1) as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3ah (a colorless oil, decylmethyl(4-(1,2,2-triphenylvinyl)phenyl)silane). The isolated yield was 52%.

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

[0322]

[0323] The characterization data are:

[0324] 1 H NMR (400 MHz, deuterated chloroform) δ 7.29–7.20 (m, 2H), 7.17–6.85 (m, 17H), 4.31–4.20 (m, 1H), 1.27 (m, 16H), 0.88 (t, J = 6.8 Hz, 3H), 0.81–0.72 (m, 2H), 0.27 (d, J = 3.7 Hz, 3H).

[0325] 13C NMR (101 MHz, deuterated chloroform) δ 144.6, 143.9, 143.8, 143.7, 141.3, 141.0, 134.7, 133.7, 131.5, 130.8, 127.8, 126.6, 33.3, 32.1, 29.8, 29.7, 29.5, 24.5, 22.9, 14.3, 13.5, -5.6.

[0326] 29 Si NMR (79 MHz, deuterated chloroform) δ-14.08.

[0327] HRMS(APCI)m / z:[M+H]+calcd for C 37 H 45 Si + :517.3285; found:517.3280.

[0328] Example 35

[0329] In a nitrogen-filled glove box, dimethyl(4-boronate phenyl)silane (denoted as 1ai, 0.5 mmol, 131.1 mg), decylmethylsilane (denoted as 2a, 0.6 mmol, 111.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (20:1) as the eluent. The solvent was then removed by vacuum drying to afford the compound represented by Formula 3ai (decylmethyl(4-boratephenyl)silane) as a white solid. The isolated yield was 58%.

[0330] The chemical reaction formula of the above preparation process is:

[0331]

[0332] The characterization data are:

[0333] 1 H NMR (400 MHz, deuterated chloroform) δ 7.78 (d, J = 7.8 Hz, 2H), 7.54 (d, J = 7.9 Hz, 2H), 4.34 (h, J = 3.6 Hz, 1H), 1.29 (d, J = 40.7 Hz, 28H), 0.94–0.74 (m, 5H), 0.32 (d, J = 3.8 Hz, 3H).

[0334] 13C NMR (101 MHz, deuterated chloroform) δ 140.7, 134.0, 133.8, 83.9, 33.3, 32.1, 29.8, 29.7, 29.5, 29.4, 25.0, 24.4, 22.8, 14.3, 13.4, -5.6, the 13 C signal attached to boron couldnot be observed due to quadrupolar relaxation.

[0335] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.42.

[0336] 11 B NMR (128 MHz, deuterated chloroform) δ 30.40.

[0337] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 41 BNaO2Si + :411.2861;found:411.2861.

[0338] Example 36

[0339] In a glove box filled with nitrogen, dimethyl(3-methylsulfonylaminophenyl)silane (denoted as 1aj, 0.5mmol, 114.5mg), decylmethylsilane (denoted as 2a, 0.6mmol, 111.6mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate (6:1) as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 3aj (a colorless oil, decylmethyl(3-methylsulfonamidophenyl)silane). The isolated yield was 45%.

[0340] The chemical reaction formula of the above preparation process is:

[0341]

[0342] The characterization data are:

[0343] 1H NMR (400 MHz, deuterated chloroform) δ 7.39–7.32 (m, 3H), 7.32–7.27 (m, 1H), 6.93 (s, 1H), 4.33 (h, J = 3.6 Hz, 1H), 3.02 (s, 3H), 1.42–1.22 (m, 16H), 0.95–0.74 (m, 5H), 0.33 (d, J = 3.8 Hz, 3H).

[0344] 13 C NMR (101 MHz, deuterated chloroform) δ 139.3, 136.4, 131.4, 129.3, 126.5, 121.7, 39.4, 32.0, 29.8, 29.69, 29.5, 29.4, 24.4, 22.8, 14.3, 13.3, -5.6.

[0345] 29 Si NMR (79 MHz, deuterated chloroform) δ-13.06.

[0346] HRMS(ESI)m / z:[M+Na] + calcd for C 18 H 33 NNaO2SSi + :378.1893; found:378.1894.

[0347] Example 37

[0348] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-octylsilane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 hours. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5a (a colorless oil, decylphenylsilane). The isolated yield was 68%.

[0349] The chemical reaction formula of the above preparation process is:

[0350]

[0351] The characterization data are:

[0352] 1H NMR (400 MHz, deuterated chloroform) δ 7.62–7.51 (m, 2H), 7.43–7.29 (m, 3H), 4.28 (t, J = 3.7 Hz, 2H), 1.50–1.40 (m, 2H), 1.39–1.17 (m, 10H), 0.97–0.91 (m, 2H), 0.87 (t, J = 6.9 Hz, 3H).

[0353] 13 C NMR (101 MHz, deuterated chloroform) δ 135.4, 133.0, 129.6, 128.1, 33.0, 32.0, 29.4, 25.2, 22.8, 14.3, 10.2.

[0354] 29 Si NMR (79 MHz, deuterated chloroform) δ-30.79.

[0355] Example 38

[0356] In a glove box filled with nitrogen, dimethyl (4-methylphenyl) silane (denoted as 1a1, 0.5 mmol, 75.0 mg), n-octyl silane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3 . SMe2 (2.0 min THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 5b (a colorless oil, decyl(4-methylphenyl)silane). The isolated yield was 65%.

[0357] The chemical reaction formula of the above preparation process is:

[0358]

[0359] The characterization data are:

[0360] 1 H NMR (400 MHz, deuterated chloroform) δ 7.46 (d, J = 7.7 Hz, 2H), 7.18 (d, J = 7.3 Hz, 2H), 4.26 (t, J = 3.4 Hz, 2H), 2.35 (s, 3H), 1.50–1.39 (m, 2H), 1.30 (d, J = 36.7 Hz, 10H), 0.99–0.77 (m, 5H).

[0361] 13C NMR (101 MHz, deuterated chloroform) δ 139.5, 135.4, 129.2, 128.9, 33.0, 32.0, 29.4, 25.2, 22.8, 21.7, 14.3, 10.3.

[0362] 29 Si NMR (79 MHz, deuterated chloroform) δ-31.13.

[0363] Example 39

[0364] In a glove box filled with nitrogen, dimethyl(4-cyclobutylphenyl)silane (denoted as 1am, 0.5mmol, 81.0mg), n-octylsilane (denoted as 2a, 1.25mmol, 180.0mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5c (a colorless oil, decyl(4-cyclobutylphenyl)silane). The isolated yield was 69%.

[0365] The chemical reaction formula of the above preparation process is:

[0366]

[0367] The characterization data are:

[0368] 1 H NMR (400 MHz, deuterated chloroform) δ 7.41 (d, J = 7.2 Hz, 1H), 7.25 (s, 1H), 7.05 (d, J = 7.2 Hz, 1H), 4.26 (t, J = 3.7 Hz, 2H), 3.18 (s, 4H), 1.44 (m, 2H), 1.37–1.23 (m, 10H), 0.96–0.83 (m, 5H).

[0369] 13 C NMR (101 MHz, deuterated chloroform) δ 147.8, 145.9, 133.6, 129.0, 122.3, 33.1, 32.1, 30.1, 30.0, 29.4, 25.2, 22.8, 14.3, 10.5.

[0370] 29 Si NMR (79 MHz, deuterated chloroform) δ-29.82.

[0371] HRMS (APCI) m / z: [M+H] +calcd for C 16 H 27 Si + :247.1877; found:247.1878.

[0372] Example 41

[0373] In a glove box filled with nitrogen, dimethyl(4-methoxyphenyl)silane (denoted as 1an, 0.5mmol, 81.0mg), n-octylsilane (denoted as 2a, 1.25mmol, 180.0mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5d (a colorless oil, decyl(4-methoxyphenyl)silane). The isolated yield was 67%.

[0374] The chemical reaction formula of the above preparation process is:

[0375]

[0376] The characterization data are:

[0377] 1 H NMR (400 MHz, deuterated chloroform) δ 7.48 (d, J = 8.6 Hz, 2H), 6.91 (d, J = 8.6 Hz, 2H), 4.26 (t, J = 3.7 Hz, 2H), 3.81 (s, 3H), 1.44 (m, 2H), 1.38–1.20 (m, 10H), 0.94–0.84 (m, 5H).

[0378] 13 C NMR (101 MHz, deuterated chloroform) δ 160.9, 136.8, 123.5, 113.9, 55.2, 33.0, 32.0, 29.4, 25.2, 22.8, 14.3, 10.5.

[0379] 29 Si NMR (79 MHz, deuterated chloroform) δ-31.40.

[0380] HRMS(ESI)m / z:[M+Na] + calcd for C 15 H 26 NaOSi + :273.1645; found:273.1661.

[0381] Example 42

[0382] In a nitrogen-filled glove box, dimethyl(4-benzyloxyphenyl)silane (denoted as 1z, 0.5 mmol, 121.0 mg), n-octylsilane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5e (a colorless oil, decyl(4-benzyloxyphenyl)silane). The isolated yield was 59%.

[0383] The chemical reaction formula of the above preparation process is:

[0384]

[0385] The characterization data are:

[0386] 1 H NMR (400 MHz, deuterated chloroform) δ 7.53–7.45 (m, 2H), 7.45–7.39 (m, 2H), 7.39–7.34 (m, 2H), 7.34–7.27 (m, 1H), 6.97 (d, J = 8.6 Hz, 2H), 5.05 (s, 2H), 4.26 (t, J = 3.7 Hz, 2H), 1.44 (dq, J = 15.0, 7.4, 6.5 Hz, 2H), 1.38–1.20 (m, 10H), 0.95–0.82 (m, 5H).

[0387] 13 C NMR (101 MHz, deuterated chloroform) δ 160.1, 137.0, 136.8, 128.7, 128.1, 127.6, 123.8, 114.8, 69.8, 33.0, 32.0, 29.4, 25.2, 22.8, 14.3, 10.5.

[0388] 29 Si NMR (79 MHz, deuterated chloroform) δ-31.35.

[0389] HRMS(ESI)m / z:[M+Na] + calcd for C 21 H 30 NaOSi + :349.1958; found:349.1947.

[0390] Example 43

[0391] In a nitrogen-filled glove box, dimethyl(4-difluoromethoxyphenyl)silane (denoted as 1ae, 0.5 mmol, 101.0 mg), n-octylsilane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 5f (a colorless oil, decyl(4-difluoromethoxyphenyl)silane). The isolated yield was 33%.

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

[0393]

[0394] The characterization data are:

[0395] 1 H NMR (400 MHz, deuterated chloroform) δ 7.63–7.49 (m, 2H), 7.11 (d, J = 8.4 Hz, 2H), 6.53 (t, J = 73.8 Hz, 1H), 4.27 (t, J = 3.7 Hz, 2H), 1.43 (ddt, J = 11.4, 8.6, 3.4 Hz, 2H), 1.38–1.17 (m, 10H), 1.01–0.79 (m, 5H).

[0396] 13 C NMR (101 MHz, deuterated chloroform) δ 152.6, 137.0, 129.8, 118.9, 115.9 (t, J = 259.6 Hz), 33.0, 32.0, 29.4, 25.1, 22.8, 14.3, 10.2.

[0397] 29 Si NMR (79 MHz, deuterated chloroform) δ-30.98.

[0398] 19 F NMR (377 MHz, deuterated chloroform) δ -80.70, -80.90.

[0399] Example 44

[0400] In a nitrogen-filled glove box, dimethyl(4-tert-butyldimethylsilyloxyphenyl)silane (denoted as 1ac, 0.5 mmol, 133.1 mg), n-octylsilane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3. SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5g (a colorless oil, decyl(4-tert-butyldimethylsilyloxyphenyl)silane). The isolated yield was 61%.

[0401] The chemical reaction formula of the above preparation process is:

[0402]

[0403] The characterization data are:

[0404] 1 H NMR (400 MHz, deuterated chloroform) δ 7.49–7.36 (m, 2H), 6.90–6.76 (m, 2H), 4.25 (t, J = 3.7 Hz, 2H), 1.47–1.40 (m, 2H), 1.36–1.23 (m, 10H), 0.98 (s, 9H), 0.94–0.83 (m, 5H), 0.20 (s, 6H).

[0405] 13 C NMR (101 MHz, deuterated chloroform) δ 157.2, 136.8, 124.3, 120.1, 33.0, 32.1, 29.4, 29.3, 25.8, 25.2, 22.9, 18.4, 14.3, 10.5, -4.2.

[0406] 29 Si NMR (79 MHz, deuterated chloroform) δ 20.92, -31.31.

[0407] HRMS (APCI) m / z: [M+H] + calcd for C 20 H 39 OSi2 + :351.2534; found:351.2517.

[0408] Example 45

[0409] In a glove box filled with nitrogen, dimethyl(4-trimethylphenyl)silane (denoted as 1ad, 0.5 mmol, 104.1 mg), n-octylsilane (denoted as 2a, 1.25 mmol, 180.0 mg) and BH3 .SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5h (a colorless oil, decyl(4-trimethylphenyl)silane). The isolated yield was 65%.

[0410] The chemical reaction formula of the above preparation process is:

[0411]

[0412] The characterization data are:

[0413] 1 H NMR (400 MHz, deuterated chloroform) δ 7.59–7.49 (m, 4H), 4.27 (t, J = 3.7 Hz, 2H), 1.50–1.41 (m, 2H), 1.35–1.24 (m, 10H), 0.97–0.91 (m, 2H), 0.88 (q, J = 3.7 Hz, 3H), 0.27 (s, 9H).

[0414] 13 C NMR (101 MHz, deuterated chloroform) δ 142.1, 134.6, 133.4, 132.9, 33.0, 32.0, 29.4, 25.3, 22.8, 14.3, 10.1, -1.1.

[0415] 29 Si NMR (79 MHz, deuterated chloroform) δ -3.91, -31.01.

[0416] Example 46

[0417] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-hexylsilane (denoted as 2a, 1.25 mmol, 145.1 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 hours. The resulting reaction solution was purified by silica gel column chromatography using n-pentane as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5i (a colorless oil, n-hexylphenylsilane). The isolated yield was 61%.

[0418] The chemical reaction formula of the above preparation process is:

[0419]

[0420] The characterization data are:

[0421] 1 H NMR (400 MHz, deuterated chloroform) δ 7.56 (m, 2H), 7.45–7.29 (m, 3H), 4.28 (t, J = 3.7 Hz, 2H), 1.50–1.40 (m, 2H), 1.39–1.21 (m, 6H), 0.97–0.90 (m, 2H), 0.87 (t, J = 6.9 Hz, 3H).

[0422] 13 C NMR (101 MHz, deuterated chloroform) δ 135.3, 133.0, 129.6, 128.1, 32.7, 31.6, 25.2, 22.7, 14.3, 10.2.

[0423] 29 Si NMR (79 MHz, deuterated chloroform) δ-30.79.

[0424] Example 47

[0425] In a glove box filled with nitrogen, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-cyclohexylsilane (denoted as 4c, 1.25 mmol, 142.6 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 48 h. The resulting reaction solution was purified by silica gel column chromatography using n-pentane as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 5j (cyclohexylphenylsilane) as a colorless oil. The isolated yield was 68%.

[0426] The chemical reaction formula of the above preparation process is:

[0427]

[0428] The characterization data are:

[0429] 1 H NMR (400 MHz, deuterated chloroform) δ 7.68–7.49 (m, 2H), 7.47–7.28 (m, 3H), 4.16 (d, J = 3.0 Hz, 2H), 1.73 (m, 5H), 1.25 (m, 5H), 1.16–1.02 (m, 1H).

[0430] 13 C NMR (101 MHz, deuterated chloroform) δ 135.8, 132.2, 129.6, 128.0, 29.0, 27.8, 26.7, 22.3.

[0431] 29 Si NMR (79 MHz, deuterated chloroform) δ-24.27.

[0432] Example 48

[0433] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), n-hexylsilane (denoted as 4c, 0.5 mmol, 58.1 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5k (a colorless oil, (2-(hexylsilyl)benzyl)dimethylsilane). The isolated yield was 64%.

[0434] The chemical reaction formula of the above preparation process is:

[0435]

[0436] The characterization data are:

[0437] 1 H NMR (400 MHz, deuterated chloroform) δ 7.49–7.43 (m, 1H), 7.29–7.22 (m, 1H), 7.11–7.02 (m, 2H), 4.31 (t, J = 3.8 Hz, 2H), 4.03–3.91 (m, 1H), 2.31 (d, J = 3.4 Hz, 2H), 1.50–1.41 (m, 2H), 1.40–1.33 (m, 2H), 1.30–1.25 (m, 4H), 0.98–0.90 (m, 2H), 0.87 (t, J = 6.8 Hz, 3H), 0.09 (d, J = 3.7 Hz, 6H).

[0438] 13 C NMR (101 MHz, deuterated chloroform) δ 146.7, 136.6, 130.6, 130.0, 128.4, 124.0, 32.7, 31.7, 25.5, 25.0, 22.7, 14.3, 10.2, -4.2.

[0439] 29 Si NMR (79 MHz, deuterated chloroform) δ -11.28, -34.98.

[0440] Example 49

[0441] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), n-octylsilane (denoted as 4c, 0.5 mmol, 72.1 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 51 (a colorless oil, dimethyl(2-octylsilyl)benzyl)silane). The isolated yield was 57%.

[0442] The chemical reaction formula of the above preparation process is:

[0443]

[0444] The characterization data are:

[0445] 1 H NMR (400 MHz, deuterated chloroform) δ 7.50–7.43 (m, 1H), 7.29–7.21 (m, 1H), 7.10–7.01 (m, 2H), 4.31 (t, J = 3.8 Hz, 2H), 4.01–3.91 (m, 1H), 2.31 (d, J = 3.4 Hz, 2H), 1.51–1.41 (m, 2H), 1.40–1.33 (m, 2H), 1.31–1.24 (m, 8H), 0.98–0.91 (m, 2H), 0.87 (t, J = 6.8 Hz, 3H), 0.09 (d, J = 3.7 Hz, 6H).

[0446] 13 C NMR (101 MHz, deuterated chloroform) δ 146.7, 136.6, 130.6, 130.0, 128.4, 124.0, 33.1, 32.1, 29.4, 25.5, 25.1, 22.8, 14.3, 10.2, -4.2.

[0447] 29 Si NMR (79 MHz, deuterated chloroform) δ-11.29, -34.99.

[0448] Example 50

[0449] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), n-decylsilane (denoted as 4d, 0.5 mmol, 86.1 mg) and BH3 . SMe2 (2.0 M inTHF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5m (a colorless oil, (2-(decylsilyl)benzyl)dimethylsilane). The isolated yield was 70%.

[0450] The chemical reaction formula of the above preparation process is:

[0451]

[0452] The characterization data are:

[0453] 1 H NMR (400 MHz, deuterated chloroform) δ 7.47 (dd, J = 7.3, 1.3 Hz, 1H), 7.31–7.23 (m, 1H), 7.12–7.02 (m, 2H), 4.31 (t, J = 3.8 Hz, 2H), 4.01–3.91 (m, 1H), 2.31 (d, J = 3.4 Hz, 2H), 1.49–1.41 (m, 2H), 1.38–1.24 (m, 14H), 0.97–0.91 (m, 2H), 0.88 (t, J = 6.9 Hz, 3H), 0.09 (d, J = 3.7 Hz, 6H).

[0454] 13 C NMR (101 MHz, deuterated chloroform) δ 146.7, 136.6, 130.6, 130.0, 128.4, 124.0, 33.1, 32.1, 29.8, 29.7, 29.5, 29.4, 25.5, 25.0, 22.9, 14.3, 10.2, -4.2.

[0455] 29 Si NMR (79 MHz, deuterated chloroform) δ-11.27, -34.98.

[0456] Example 51

[0457] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), n-octadecylsilane (denoted as 4e, 0.5 mmol, 142.1 mg) and BH3 . SMe2 (2.0 M inTHF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5n (a colorless oil, dimethyl(2-(octadecylsilyl)benzyl)silane). The isolated yield was 60%.

[0458] The chemical reaction formula of the above preparation process is:

[0459]

[0460] The characterization data are:

[0461] 1 H NMR (400 MHz, deuterated chloroform) δ 7.51–7.43 (m, 1H), 7.29–7.22 (m, 1H), 7.10–7.02 (m, 2H), 4.31 (t, J = 3.8 Hz, 2H), 4.02–3.91 (m, 1H), 2.31 (d, J = 3.4 Hz, 2H), 1.51–1.40 (m, 2H), 1.38–1.26 (m, 30H), 0.98–0.91 (m, 2H), 0.88 (t, J = 6.8 Hz, 3H), 0.09 (d, J = 3.7 Hz, 6H).

[0462] 13 C NMR (101 MHz, deuterated chloroform) δ 146.7, 136.6, 130.6, 130.0, 128.40, 124.0, 33.1, 32.1, 29.9, 29.8, 29.7, 29.6, 29.5, 25.5, 25.0, 22.9, 14.3, 10.2, -4.2.

[0463] 29 Si NMR (79 MHz, deuterated chloroform) δ -11.28, -34.99.

[0464] Example 52

[0465] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), (2-(naphthalen-2-yl)ethyl)silane (denoted as 4f, 0.5 mmol, 93.0 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5o (a colorless oil, dimethyl(2-(2-naphth-2-yl)ethyl)silyl)benzyl)silane). The isolated yield was 51%.

[0466] The chemical reaction formula of the above preparation process is:

[0467]

[0468] The characterization data are:

[0469] 1 H NMR (400 MHz, deuterated chloroform) δ 7.85–7.70 (m, 3H), 7.61 (s, 1H), 7.49 (dd, J = 7.3, 1.3 Hz, 1H), 7.41 (pd, J = 6.9, 1.5 Hz, 2H), 7.33 (dd, J = 8.4, 1.7 Hz, 1H), 7.28 (td, J = 7.6, 1.5 Hz, 1H), 7.13–7.02 (m, 2H), 4.39 (t, J = 3.7 Hz, 2H), 4.03–3.91 (m, 1H), 3.00–2.87 (m, 2H), 2.31 (d, J = 3.4 Hz, 2H), 1.45–1.33 (m, 2H), 0.08 (d, J = 3.7 Hz, 6H).

[0470] 13 C NMR (101 MHz, deuterated chloroform) δ 146.8, 141.7, 136.7, 133.8, 132.1, 130.2, 129.9, 128.5, 128.0, 127.7, 127.6, 127.1, 126.0, 125.8, 125.2, 124.1, 31.7, 25.1, 12.1, −4.2.

[0471] 29 Si NMR (79 MHz, deuterated chloroform) δ -11.11, -35.04.

[0472] Example 53

[0473] In a nitrogen-filled glove box, 7,7-dimethyl-7-silabicyclo[4.2.0]octa-1,3,5-triene (denoted as 1ao, 0.8 mmol, 118.5 mg), cyclohexylsilane (denoted as 4c, 0.5 mmol, 57.0 mg) and BH3 . SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 60°C for 24 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 5p (a colorless oil, (2-(cyclohexylsilyl)benzyl)dimethylsilane). The isolated yield was 42%.

[0474] The chemical reaction formula of the above preparation process is:

[0475]

[0476] The characterization data are:

[0477] 1 H NMR (400 MHz, deuterated chloroform) δ 7.51–7.42 (m, 1H), 7.28–7.22 (m, 1H), 7.09–7.02 (m, 2H), 4.18 (d, J = 3.1 Hz, 2H), 3.99–3.91 (m, 1H), 2.29 (d, J = 3.4 Hz, 2H), 1.78–1.66 (m, 5H), 1.26–1.10 (m, 6H), 0.08 (d, J = 3.7 Hz, 6H).

[0478] 13 C NMR (101 MHz, deuterated chloroform) δ 146.7, 137.2, 129.9, 128.4, 123.9, 29.4, 27.9, 26.8, 25.3, 22.2, -4.2.

[0479] 29 Si NMR (79 MHz, deuterated chloroform) δ-11.26, -27.98.

[0480] Example 54

[0481] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), diethylsilane (denoted as 6a, 0.6 mmol, 52.8 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using n-pentane as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7a (a colorless oil, diethylphenylsilane). The isolated yield was 53%.

[0482] The chemical reaction formula of the above preparation process is:

[0483]

[0484] The characterization data are:

[0485] 1 H NMR (400 MHz, deuterated chloroform) δ 7.53 (m, 2H), 7.35 (m, 3H), 4.21 (p, J = 3.3 Hz, 1H), 1.01 (t, J = 7.8 Hz, 6H), 0.90–0.79 (m, 4H).

[0486] 13 C NMR (101 MHz, deuterated chloroform) δ 135.7, 134.8, 129.3, 127.9, 8.3, 3.6.

[0487] 29 Si NMR (79 MHz, deuterated chloroform) δ-5.09.

[0488] Example 55

[0489] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), dicyclopentylsilane (denoted as 6b, 0.6 mmol, 100.9 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7b (dicyclopentylphenylsilane) as a colorless oil. The isolated yield was 51%.

[0490] The chemical reaction formula of the above preparation process is:

[0491]

[0492] The characterization data are:

[0493] 1H NMR (400 MHz, deuterated chloroform) δ 7.57–7.48 (m, 2H), 7.38–7.26 (m, 3H), 4.11 (t, J = 3.4 Hz, 1H), 1.89 (tdt, J = 11.5, 7.4, 3.1 Hz, 2H), 1.82–1.69 (m, 2H), 1.61–1.19 (m, 15H).

[0494] 13 C NMR (101 MHz, deuterated chloroform) δ 135.9, 135.4, 129.1, 127.7, 29.5, 29.4, 27.1, 26.8, 23.0.

[0495] 29 Si NMR (79 MHz, deuterated chloroform) δ-0.79.

[0496] HRMS(ESI)m / z:[M+Na] + calcd for C 16 H 24 NaSi + :267.1539; found:267.1542.

[0497] Example 56

[0498] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), di-n-pentylsilane (denoted as 6c, 0.6 mmol, 103.3 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7c (a colorless oil, di-n-pentylphenylsilane). The isolated yield was 67%.

[0499] The chemical reaction formula of the above preparation process is:

[0500]

[0501] The characterization data are:

[0502] 1 H NMR (400 MHz, deuterated chloroform) δ 7.58–7.43 (m, 2H), 7.40–7.23 (m, 3H), 4.26 (p, J = 3.4 Hz, 1H), 1.42–1.24 (m, 12H), 0.93–0.75 (m, 10H).

[0503] 13 C NMR (101 MHz, deuterated chloroform) δ 136.3, 134.8, 129.2, 127.9, 35.7, 22.5, 14.2, 12.0.

[0504] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.34.

[0505] HRMS(ESI)m / z:[M+Na] + calcd for C 16 H 28 NaSi + :271.1852;found:271.1861.

[0506] Example 57

[0507] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), di-n-octylsilane (denoted as 6d, 0.6 mmol, 153.8 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7d (a colorless oil, di-n-octylphenylsilane). The isolated yield was 72%.

[0508] The chemical reaction formula of the above preparation process is:

[0509]

[0510] The characterization data are:

[0511] 1 H NMR (400 MHz, deuterated chloroform) δ 7.59–7.46 (m, 2H), 7.42–7.26 (m, 3H), 4.25 (p, J = 3.4 Hz, 1H), 1.41–1.22 (m, 24H), 0.93–0.77 (m, 10H).

[0512] 13 C NMR (101 MHz, deuterated chloroform) δ 136.3, 134.8, 129.2, 127.9, 33.4, 32.1, 29.4, 24.6, 22.8, 14.3, 12.0.

[0513] 29Si NMR (79 MHz, deuterated chloroform) δ-9.43.

[0514] Example 58

[0515] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), bis(2-ethylhexyl)silane (denoted as 6e, 0.6 mmol, 153.8 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7e (a colorless oil, bis(2-ethylhexyl)(phenyl)silane). The isolated yield was 56%.

[0516] The chemical reaction formula of the above preparation process is:

[0517]

[0518] The characterization data are:

[0519] 1 H NMR (400 MHz, deuterated chloroform) δ 7.59–7.41 (m, 2H), 7.40–7.25 (m, 3H), 4.39 (p, J = 2.9, 2.3 Hz, 1H), 1.42 (dq, J = 12.4, 6.0 Hz, 2H), 1.35–1.13 (m, 17H), 0.89–0.76 (m, 15H).

[0520] 13 C NMR (101 MHz, deuterated chloroform) δ 137.2, 134.8, 129.1, 127.9, 35.9, 35.8, 35.6, 35.5, 28.9, 28.8, 28.7, 23.2, 23.1, 17.8, 14.3, 10.9, 10.8.

[0521] 29 Si NMR (79 MHz, deuterated chloroform) δ-12.39.

[0522] HRMS(ESI)m / z:[M+H] + calcd for C 22 H 41 Si + :333.2972; found:333.2961.

[0523] Example 59

[0524] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-octylphenethylsilane (denoted as 6f, 0.6 mmol, 148.9 mg) and BH3 . SMe2 (2.0 min THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7f (a colorless oil, n-octylphenethylphenylsilane). The isolated yield was 53%.

[0525] The chemical reaction formula of the above preparation process is:

[0526]

[0527] The characterization data are:

[0528] 1 H NMR (400 MHz, deuterated chloroform) δ 7.62–7.44 (m, 2H), 7.43–7.31 (m, 3H), 7.30–7.21 (m, 2H), 7.16 (dd, J = 7.7, 3.0 Hz, 3H), 4.31 (p, J = 3.4 Hz, 1H), 2.79–2.50 (m, 2H), 1.42–1.18 (m, 14H), 0.96–0.79 (m, 5H).

[0529] 13 C NMR (101 MHz, deuterated chloroform) δ 144.8, 135.6, 134.8, 129.4, 128.5, 128.04, 127.96, 125.8, 33.4, 32.1, 30.8, 29.4, 24.6, 22.8, 14.3, 14.2, 12.0.

[0530] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.49.

[0531] HRMS(ESI)m / z:[M+Na] + calcd for C 22 H 32 NaSi + :347.2165; found:347.2151.

[0532] Example 60

[0533] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5mmol, 68.0mg), n-decylphenethylsilane (denoted as 6g, 0.6mmol, 165.7mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7g (a colorless oil, n-decylphenethylphenylsilane). The isolated yield was 46%.

[0534] The chemical reaction formula of the above preparation process is:

[0535]

[0536] The characterization data are:

[0537] 1 H NMR (400 MHz, deuterated chloroform) δ 7.58–7.49 (m, 2H), 7.40–7.32 (m, 3H), 7.28–7.22 (m, 2H), 7.19–7.11 (m, 3H), 4.31 (p, J = 3.4 Hz, 1H), 2.75–2.63 (m, 2H), 1.43–1.18 (m, 18H), 0.94–0.80 (m, 5H).

[0538] 13 C NMR (101 MHz, deuterated chloroform) δ 144.8, 135.6, 134.8, 129.4, 128.5, 128.04, 127.96, 125.8, 32.1, 30.8, 29.8, 29.7, 29.5, 29.4, 24.6, 22.9, 14.3, 14.2, 12.0.

[0539] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.48.

[0540] HRMS(ESI)m / z:[M+Na] + calcd for C 24 H 36 NaSi + :375.2478; found:375.2485.

[0541] Example 61

[0542] In a nitrogen-filled glove box, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-octyl(3-phenylpropyl)silane (denoted as 6h, 0.6 mmol, 157.3 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 7h (a colorless oil, n-octyl(3-phenylpropyl)phenylsilane). The isolated yield was 61%.

[0543] The chemical reaction formula of the above preparation process is:

[0544]

[0545] The characterization data are:

[0546] 1 H NMR (400 MHz, deuterated chloroform) δ 7.49 (dd, J = 7.2, 1.7 Hz, 2H), 7.40–7.28 (m, 3H), 7.24 (t, J = 7.3 Hz, 2H), 7.18–7.06 (m, 3H), 4.28 (h, J = 3.9, 3.3 Hz, 1H), 2.62 (t, J = 7.6 Hz, 2H), 1.70 (m, 2H), 1.42–1.19 (m, 12H), 0.86 (m, 7H).

[0547] 13 C NMR (101 MHz, deuterated chloroform) δ 142.5, 134.8, 129.3, 128.6, 128.4, 125.8, 39.6, 33.4, 32.1, 29.4, 26.7, 22.8, 14.3, 12.0, 11.9.

[0548] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.38.

[0549] Example 62

[0550] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-pentyl-n-octylsilane (denoted as 6i, 0.6 mmol, 128.5 mg) and BH3 .SMe2 (2.0 min THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7i (a colorless oil, n-pentyl-n-octylphenylsilane). The isolated yield was 52%.

[0551] The chemical reaction formula of the above preparation process is:

[0552]

[0553] The characterization data are:

[0554] 1 H NMR (400 MHz, deuterated chloroform) δ 7.60–7.43 (m, 2H), 7.34 (m, 3H), 4.25 (p, J = 3.4 Hz, 1H), 1.39–1.22 (m, 18H), 0.85 (m, 5.0 Hz, 10H).

[0555] 13 C NMR (101 MHz, deuterated chloroform) δ 136.3, 134.8, 129.2, 127.9, 35.6, 33.4, 32.1, 24.7, 24.3, 22.4, 14.3, 14.1, 12.1, 12.0.

[0556] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.38.

[0557] HRMS(ESI)m / z:[M+Na] + calcd for C 19 H 34 NaSi + :313.2322;found:313.2323.

[0558] Example 63

[0559] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-octyl(3-phenoxypropyl)silane (denoted as 6j, 0.6 mmol, 166.9 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to obtain the compound represented by Formula 7j (a colorless oil, n-octyl(3-phenoxypropyl)phenylsilane). The isolated yield was 58%.

[0560] The chemical reaction formula of the above preparation process is:

[0561]

[0562] The characterization data are:

[0563] 1 H NMR (400 MHz, deuterated chloroform) δ 7.44 (dd, J = 4.4, 2.3 Hz, 2H), 7.30–7.20 (m, 3H), 7.15 (t, J = 7.7 Hz, 2H), 6.85–6.78 (m, 1H), 6.78–6.72 (m, 2H), 4.24 (p, J = 3.2 Hz, 1H), 3.80 (t, J = 6.6 Hz, 2H), 1.76 (dq, J = 13.2, 6.6 Hz, 2H), 1.36–1.13 (m, 12H), 0.94–0.84 (m, 2H), 0.79 (q, J = 6.9, 6.2 Hz, 5H).

[0564] 13 C NMR (101 MHz, deuterated chloroform) δ 159.2, 129.5, 129.4, 128.0, 120.6, 114.6, 70.1, 33.4, 32.0, 29.4, 24.6, 22.8, 14.3, 12.0, 8.3.

[0565] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.08.

[0566] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 34 NaOSi + :377.2271;found:377.2271.

[0567] Example 64

[0568] In a glove box filled with nitrogen, dimethylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), (5-(benzyloxy)pentyl)octylsilane (denoted as 6k, 0.6 mmol, 192.2 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to afford the compound represented by Formula 7k (a colorless oil, (5-(benzyloxy)pentyl)(octyl)(phenyl)silane). The isolated yield was 61%.

[0569] The chemical reaction formula of the above preparation process is:

[0570]

[0571] The characterization data are:

[0572] 1 H NMR (400 MHz, deuterated chloroform) δ 7.58–7.44 (m, 2H), 7.39–7.21 (m, 8H), 4.48 (s, 2H), 4.25 (p, J = 3.4 Hz, 1H), 3.43 (t, J = 6.6 Hz, 2H), 1.67–1.51 (m, 2H), 1.44–1.20 (m, 16H), 0.85 (m, 7H).

[0573] 13 C NMR (101 MHz, deuterated chloroform) δ 138.8, 136.1, 134.8, 129.2, 128.5, 127.9, 127.7, 127.6, 73.0, 70.5, 33.4, 32.0, 29.9, 29.5, 24.6, 24.5, 22.8, 14.3, 12.0.

[0574] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.43.

[0575] HRMS(ESI)m / z:[M+Na] + calcd for C 26 H 40 NaOSi + :419.2741; found:419.2744.

[0576] Example 65

[0577] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), n-octyl(4-chlorobutyl)silane (denoted as 6l, 0.6 mmol, 140.5 mg) and BH3 . SMe2 (2.0 min THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 71 (a colorless oil, n-octyl(4-chlorobutyl)phenylsilane). The isolated yield was 54%.

[0578] The chemical reaction formula of the above preparation process is:

[0579]

[0580] The characterization data are:

[0581] 1 H NMR (400 MHz, deuterated chloroform) δ 7.57–7.46 (m, 2H), 7.41–7.28 (m, 3H), 4.27 (p, J = 3.4 Hz, 1H), 3.50 (t, J = 6.7 Hz, 2H), 1.79 (p, J = 6.8 Hz, 2H), 1.60–1.47 (m, 2H), 1.42–1.22 (m, 12H), 0.97–0.72 (m, 7H).

[0582] 13 C NMR (101 MHz, deuterated chloroform) δ 135.7, 134.7, 129.4, 128.0, 35.9, 33.4, 32.0, 29.4, 24.6, 22.8, 22.0, 14.3, 12.0, 11.4.

[0583] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.49.

[0584] HRMS(ESI)m / z:[M+Na] + calcd for C 18 H 31 ClNaSi + :333.1776; found:333.1778.

[0585] Example 66

[0586] In a glove box filled with nitrogen, methylphenylsilane (denoted as 1ak, 0.5mmol, 68.0mg), n-octyl(5-bromopentyl)silane (denoted as 6m, 0.6mmol, 175.3mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then decompressed and dried to obtain the compound represented by Formula 7m (a colorless oil, n-octyl(5-bromopentyl)phenylsilane). The isolated yield was 66%.

[0587] The chemical reaction formula of the above preparation process is:

[0588]

[0589] The characterization data are:

[0590] 1 H NMR (400 MHz, deuterated chloroform) δ 7.54–7.47 (m, 2H), 7.38–7.29 (m, 3H), 4.26 (p, J = 3.4 Hz, 1H), 3.34 (t, J = 6.9 Hz, 2H), 1.82 (p, J = 6.9 Hz, 2H), 1.49–1.21 (m, 16H), 0.98–0.74 (m, 7H).

[0591] 13 C NMR (101 MHz, deuterated chloroform) δ 135.9, 134.7, 129.3, 128.0, 33.9, 33.4, 32.6, 32.0, 31.8, 29.4, 24.6, 23.9, 22.8, 14.3, 12.0.

[0592] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.41.

[0593] Example 67

[0594] In a glove box filled with nitrogen, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), octyl(5-(thien-2-yl)pentyl)silane (denoted as 6n, 0.6 mmol, 177.7 mg) and BH3 .SMe2 (2.0 M in THF, 20 mol%, 50 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7n (octyl(phenyl)(5-(thiophen-2-yl)pentyl)silane) as a colorless oil. The isolated yield was 36%.

[0595] The chemical reaction formula of the above preparation process is:

[0596]

[0597] The characterization data are:

[0598] 1 H NMR (400 MHz, deuterated chloroform) δ 7.58–7.45 (m, 2H), 7.42–7.27 (m, 3H), 7.11–7.05 (m, 1H), 6.89 (dd, J = 5.0, 3.4 Hz, 1H), 6.78–6.70 (m, 1H), 4.25 (p, J = 3.3 Hz, 1H), 2.78 (t, J = 7.6 Hz, 2H), 1.65 (p, J = 7.3 Hz, 2H), 1.43–1.22 (m, 16H), 0.85 (dt, J = 13.5, 7.0 Hz, 7H).

[0599] 13 C NMR (101 MHz, deuterated chloroform) δ 145.9, 134.8, 129.3, 128.0, 126.8, 124.0, 122.9, 33.4, 32.8, 32.1, 31.5, 29.9, 29.4, 24.6, 24.4, 22.8, 14.3, 12.1, 12.0.

[0600] 29 Si NMR (79 MHz, deuterated chloroform) δ 9.38.

[0601] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 36 NaSSi + :395.2199; found:395.2197.

[0602] Example 68

[0603] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), 1-(5-(octylsilyl)pentyl)-1H-pyrrole (denoted as 6o, 0.6 mmol, 167.5 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7o (a pale yellow oil, 1-(5-(octyl(phenyl)silyl)pentyl)1H-pyrrole). The isolated yield was 60%.

[0604] The chemical reaction formula of the above preparation process is:

[0605]

[0606] The characterization data are:

[0607] 1 H NMR (400 MHz, deuterated chloroform) δ 7.54–7.44 (m, 2H), 7.33 (qd, J = 5.2, 1.9 Hz, 3H), 6.59 (t, J = 2.1 Hz, 2H), 6.11 (t, J = 2.1 Hz, 2H), 4.24 (p, J = 3.4 Hz, 1H), 3.79 (t, J = 7.2 Hz, 2H), 1.71 (p, J = 7.4 Hz, 2H), 1.43–1.19 (m, 16H), 0.93–0.73 (m, 7H).

[0608] 13 C NMR (101 MHz, deuterated chloroform) δ 135.9, 134.7, 129.3, 128.0, 120.5, 107.9, 49.6, 32.0, 31.3, 30.4, 29.3, 24.6, 24.3, 22.8, 14.2, 12.0.

[0609] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.41.

[0610] HRMS(ESI)m / z:[M+Na] + calcd for C 23 H 37 NNaSi + :378.2587; found:378.2591.

[0611] Example 69

[0612] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), 1-(5-(octylsilyl)pentyl)-1H-indole (denoted as 6p, 0.6 mmol, 197.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7p (a pale yellow oil, 1-(5-(octyl(phenyl)silyl)pentyl)1H-indole). The isolated yield was 40%.

[0613] The chemical reaction formula of the above preparation process is:

[0614]

[0615] The characterization data are:

[0616] 1 H NMR (400 MHz, deuterated chloroform) δ 7.61 (d, J = 7.9 Hz, 1H), 7.48 (dd, J = 7.2, 1.9 Hz, 2H), 7.38–7.25 (m, 4H), 7.17 (dd, J = 8.9, 6.0 Hz, 1H), 7.07 (t, J = 7.4 Hz, 1H), 7.02 (d, J = 3.1 Hz, 1H) ,6.45(d,J=3.1Hz,1H),4.23(p,J=3.3Hz,1H),4.03(t,J=7.1Hz,2H),1.78(p,J=7 .2Hz,2H),1.46–1.16(m,16H),0.86(t,J=6.8Hz,3H),0.80(tt,J=8.2,3.6Hz,4H).

[0617] 13 C NMR (101 MHz, deuterated chloroform) δ 136.1, 135.9, 134.7, 129.3, 128.0, 127.9, 121.4, 121.1, 119.3, 109.5, 101.0, 46.4, 33.4, 32.0, 30.6, 30.0, 29.4, 24.6, 24.3, 22.8, 14.3, 12.0.

[0618] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.35.

[0619] HRMS(ESI)m / z:[M+Na] + calcd for C27 H 39 NNaSi + :428.2744; found:428.2746.

[0620] Example 70

[0621] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), 9-(5-(octylsilyl)pentyl)-9H-carbazole (denoted as 6q, 0.6 mmol, 227.6 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7q (9-(5-(octyl(phenyl)silyl)pentyl)9H-carbazole) as a colorless oil. The isolated yield was 59%.

[0622] The chemical reaction formula of the above preparation process is:

[0623]

[0624] The characterization data are:

[0625] 1 H NMR (400 MHz, deuterated chloroform) δ 8.06 (d, J = 7.7 Hz, 2H), 7.46 (dt, J = 5.4, 2.0 Hz, 2H), 7.40 (td, J = 7.7, 7.2, 1.1 Hz, 2H), 7.35–7.25 (m, 5H), 7.22–7.14 (m, 2H), 4.22 (p, J = 3.4 Hz, 1H), 4.16 (t, J = 7.2 Hz, 2H), 1.77 (p, J = 7.2 Hz, 2H), 1.41–1.17 (m, 16H), 0.86 (t, J = 6.9 Hz, 3H), 0.82–0.67 (m, 4H).

[0626] 13 C NMR (101 MHz, deuterated chloroform) δ 140.5, 135.9, 134.7, 129.3, 128.0, 125.7, 122.9, 120.4, 118.8, 108.7, 43.0, 33.4, 32.0, 30.9, 29.4, 28.7, 24.6, 24.5, 22.8, 14.3, 12.0.

[0627] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.25.

[0628] HRMS(ESI)m / z:[M+Na] + calcd for C 31 H 41 NNaSi + :478.2900; found:478.2897.

[0629] Example 71

[0630] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), N,4-dimethyl-N-(3-(octylsilyl)propyl)benzenesulfonamide (denoted as 6r, 0.6 mmol, 221.5 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether / ethyl acetate as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7r (a colorless oil, N,4-dimethyl-N-(3-(octyl(phenyl)silyl)propyl)benzenesulfonamide). The isolated yield was 57%.

[0631] The chemical reaction formula of the above preparation process is:

[0632]

[0633] The characterization data are:

[0634] 1 H NMR (400 MHz, deuterated chloroform) δ 7.62 (d, J = 8.3 Hz, 2H), 7.53–7.46 (m, 2H), 7.39–7.30 (m, 3H), 7.27 (d, J = 8.0 Hz, 2H), 4.26 (p, J = 3.4 Hz, 1H), 2.96 (t, J = 7.2 Hz, 2H), 2.63 (s, 3H), 2.40 (s, 3H), 1.57 (dddt, J = 14.0, 9.5, 7.2, 3.9 Hz, 2H), 1.42–1.22 (m, 12H), 0.92–0.79 (m, 7H).

[0635] 13 C NMR (101 MHz, deuterated chloroform) δ 143.2, 134.8, 134.7, 129.7, 129.4, 128.0, 127.4, 52.8, 34.6, 33.3, 32.0, 29.3, 24.5, 22.8, 22.7, 21.5, 14.2, 11.9, 8.9.

[0636] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.08.

[0637] HRMS(ESI)m / z:[M+Na] + calcd for C 25 H 39 NNaO2SSi + :468.2363; found:468.2369.

[0638] Example 72

[0639] In a nitrogen-filled glove box, methylphenylsilane (denoted as 1ak, 0.5 mmol, 68.0 mg), (5-cyclohexylpentyl)(octyl)silane (denoted as 6s, 0.6 mmol, 177.8 mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7s (a colorless oil, (5-cyclohexylpentyl)(octyl)(phenyl)silane). The isolated yield was 66%.

[0640] The chemical reaction formula of the above preparation process is:

[0641]

[0642] The characterization data are:

[0643] 1 H NMR (400 MHz, deuterated chloroform) δ 7.61–7.41 (m, 2H), 7.38–7.27 (m, 3H), 4.24 (p, J = 3.3 Hz, 1H), 1.67 (m, 5H), 1.34–1.13 (m, 18H), 0.84 (m, 9H).

[0644] 13 C NMR (101 MHz, deuterated chloroform) δ 134.8, 129.2, 127.9, 40.7, 33.4, 33.1, 33.1, 32.2, 32.1, 29.4, 26.9, 26.6, 24.7, 22.9, 14.3, 12.0, 9.1.

[0645] 29 Si NMR (79 MHz, deuterated chloroform) δ-8.75.

[0646] HRMS(ESI)m / z:[M+Na] + calcd for C 22 H 38 NaSi + :353.2635; found:353.2651.

[0647] Example 73

[0648] In a nitrogen-filled glove box, dimethyl(4-benzyloxy)phenylsilane (denoted as 1z, 0.5 mmol, 121.1 mg), (5-cyclohexylpentyl)(octyl)silane (denoted as 6s, 0.6 mmol, 177.8 mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to afford the compound represented by Formula 7t (a colorless oil, (4-(phenoxy)phenyl)(5-cyclohexylpentyl)(octyl)silane). The isolated yield was 52%.

[0649] The chemical reaction formula of the above preparation process is:

[0650]

[0651] The characterization data are:

[0652] 1 H NMR (400 MHz, deuterated chloroform) δ 7.46–7.39 (m, 4H), 7.39–7.33 (m, 2H), 7.33–7.27 (m, 1H), 6.99–6.93 (m, 2H), 5.04 (s, 2H), 4.22 (p, J = 3.3 Hz, 1H), 1.76–1.58 (m, 5H), 1.39–1.08 (m, 18H), 0.91–0.76 (m, 9H).

[0653] 13 C NMR (101 MHz, deuterated chloroform) δ 159.9, 137.2, 136.2, 128.7, 128.1, 127.6, 114.6, 69.9, 40.7, 33.4, 33.11, 33.10, 32.1, 32.0, 29.4, 26.9, 26.6, 24.6, 22.8, 14.3, 12.3, 9.3.

[0654] 29 Si NMR (79 MHz, deuterated chloroform) δ-9.34.

[0655] HRMS(ESI)m / z:[M+Na] + calcd for C 29 H 44 NaOSi + :459.3054; found:459.3057.

[0656] Example 74

[0657] In a glove box filled with nitrogen, b-cyclo[4.2.0]octa-1(6),2,4-trien-3-yldimethylsilane (denoted as 1am, 0.5mmol, 81.0mg), (5-cyclohexylpentyl)(octyl)silane (denoted as 6s, 0.6mmol, 177.8mg) and BH3 . SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then removed by vacuum drying to afford the compound represented by Formula 7u (a colorless oil, bis[4.2.0]octa-1,3,5-trien-3-yl(5-cyclohexylpentyl)(octyl)silane). The isolated yield was 68%.

[0658] The chemical reaction formula of the above preparation process is:

[0659]

[0660] The characterization data are:

[0661] 1 H NMR (400 MHz, deuterated chloroform) δ 7.35 (d, J = 7.2 Hz, 1H), 7.20 (s, 1H), 7.03 (d, J = 7.2 Hz, 1H), 4.21 (p, J = 3.3 Hz, 1H), 3.17 (s, 4H), 1.75–1.61 (m, 5H), 1.35–1.12 (m, 18H), 0.90–0.77 (m, 9H).

[0662] 13 C NMR (101 MHz, deuterated chloroform) δ 147.3, 134.2, 133.1, 128.5, 122.1, 40.7, 33.5, 33.13, 33.11, 32.2, 32.1, 30.1, 29.9, 29.4, 27.0, 26.6, 24.7, 22.9, 14.8, 12.3, 9.3.

[0663] 29 Si NMR (79 MHz, deuterated chloroform) δ-7.83.

[0664] Example 75

[0665] In a nitrogen-filled glove box, dimethyl(4-trimethylsilylphenyl)silane (denoted as 1ad, 0.5 mmol, 104.1 mg), (5-cyclohexylpentyl)(octyl)silane (denoted as 6s, 0.6 mmol, 177.8 mg) and BH3 . SMe2 (2.0 M inTHF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7v (a colorless oil, (4-((5-cyclohexylpentyl)(octyl)silyl)phenyl)trimethylsilane). The isolated yield was 65%.

[0666] The chemical reaction formula of the above preparation process is:

[0667]

[0668] The characterization data are:

[0669] 1 H NMR (400 MHz, deuterated chloroform) δ 7.50 (s, 4H), 4.29–4.18 (m, 1H), 1.70 (t, J = 15.5 Hz, 5H), 1.34–1.14 (m, 18H), 0.89–0.80 (m, 9H), 0.26 (s, 9H).

[0670] 13 C NMR (101 MHz, deuterated chloroform) δ 136.8, 134.1, 132.8, 40.7, 33.5, 33.1, 32.2, 32.1, 27.0, 26.6, 24.7, 22.9, 14.3, 9.0, -1.0.

[0671] 29 Si NMR (79 MHz, deuterated chloroform) δ -4.12, -9.04.

[0672] Example 76

[0673] In a nitrogen-filled glove box, tert-butyl(4-(dimethylsilyl)phenoxy)dimethylsilane (denoted as 1ac, 0.5 mmol, 133.1 mg), (5-cyclohexylpentyl)(octyl)silane (denoted as 6s, 0.6 mmol, 177.8 mg) and BH3 .SMe2 (2.0 M in THF, 10 mol%, 25 μL) was mixed in a 15 mL pressure tube containing a magnetic rod and stirred at 100°C for 36 h. The resulting reaction solution was purified by silica gel column chromatography using petroleum ether as the eluent. The solvent was then evaporated to dryness under reduced pressure to obtain the compound represented by Formula 7w (a colorless oil, tert-butyl(4-((5-cyclohexylpentyl)(octyl)silyl)phenoxy)dimethylsilane). The isolated yield was 57%.

[0674] The chemical reaction formula of the above preparation process is:

[0675]

[0676] The characterization data are:

[0677] 1 H NMR (400 MHz, deuterated chloroform) δ 7.41 (d, J = 8.2 Hz, 2H), 6.86 (d, J = 8.2 Hz, 2H), 4.25 (p, J = 3.2 Hz, 1H), 1.80–1.63 (m, 5H), 1.44–1.12 (m, 18H), 1.03 (s, 9H), 0.95–0.80 (m, 9H), 0.25 (s, 6H).

[0678] 13 C NMR (101 MHz, deuterated chloroform) δ 156.8, 136.1, 119.8, 40.7, 33.4, 32.2, 32.1, 29.4, 29.4, 27.0, 26.6, 25.8, 24.7, 22.9, 18.4, 14.3, 12.3, 9.3, -4.2.

[0679] 29 Si NMR (79 MHz, deuterated chloroform) δ 20.51, -9.39.

[0680] HRMS(ESI)m / z:[M+Na] + calcd for C 28 H 52 NaOSi + :483.3449;found:483.3449.

Claims

1. A method for preparing a polysubstituted hydrosilane compound, characterized in that: The method comprises the following steps: in a protective atmosphere, carrying out a silane recombination reaction on an arylhydrosilane compound, an alkylhydrosilane compound and a tetrahydrofuran solution of borane dimethyl sulfide at 60-100°C, reacting for 24-48 hours, and then performing rapid column chromatography purification to obtain a polysubstituted hydrogen silane compound; the arylhydrosilane compound has one of the following structural formulas: ArSiMeH2 or ArSiMe2H or , wherein: the Ar is one of N-methylindole, N-phenylcarbazole, 1-naphthalene, 2-naphthalene, 9-phenanthrene, 4-pyrene, 4-dibenzothiophene, phenyl, and substituted phenyl; the substituent in the substituted phenyl is one of methyl, 2,3-dimethyl, ethyl, isopropyl, methoxy, tert-butyl, phenyl, methylthio, N,N-dimethyl, morpholinyl, chlorine, cyclobutyl, adamantyl, benzyl ether, trimethylsilyl, difluoromethoxy, trifluoromethoxy, trifluoromethylthio, borate, and sulfonamide; the alkyl hydrogen silane compound is selected from decylmethylsilane, n-octylsilane, n-hexylsilane, n-cyclohexylsilane, n-decylsilane, n-octadecylsilane, (2-(naphthalene-2-yl)ethyl)silane, diethylsilane, dicyclopentylsilane, di-n-pentylsilane, di-n-octylsilane, bis(2 -ethylhexyl)silane, n-octylphenethylsilane, n-decylphenethylsilane, n-octyl(3-phenylpropyl)silane, n-pentyl-n-octylsilane, n-octyl(3-phenoxypropyl)silane, (5-(benzyloxy)pentyl)octylsilane, n-octyl(4-chlorobutyl)silane, n-octyl(5-bromopentyl)silane, octyl(5-(thien-2-yl)pentyl)silane, 1-(5-(octylsilyl)pentyl)-1H-pyrrole, 1-(5-(octylsilyl)pentyl)-1H-indole, 9-(5-(octylsilyl)pentyl)-9H-carbazole, N,4-dimethyl-N-(3-(octylsilyl)propyl)benzenesulfonamide, (5-cyclohexylpentyl)(octyl)silane.

2. The method for preparing a polysubstituted hydrosilane compound according to claim 1, wherein: The molar ratio of the arylhydrogensilane compound to the alkylhydrogensilane compound is 1:1.2-2.

5.

3. The method for preparing a polysubstituted hydrosilane compound according to claim 1, wherein: The concentration of the tetrahydrofuran solution of borane dimethyl sulfide is 2.0 mol / L; the amount of the tetrahydrofuran solution of borane dimethyl sulfide used is 10-20 mol% of the amount of the arylhydrosilane compound used.

4. The method for preparing a polysubstituted hydrosilane compound according to claim 1, wherein: The protective atmosphere is a nitrogen atmosphere or an argon atmosphere.

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