Preparation method of allylsilane compounds

Abstract

The present invention provides a method for preparing allylsilane compounds. Using allyl acetate and tert-butyldiphenylsilylformic acid as starting materials, the reaction is carried out in the presence of a photocatalyst, a metal catalyst, a ligand, and a base to obtain allylsilane compounds. The method of the present invention does not require the use of expensive noble metal catalysts and photocatalysts, has mild reaction conditions, good substrate generality, and a relatively high reaction yield.

Description

Technical Field

[0001] The present invention belongs to the technical field of organic synthesis, and particularly relates to a method for preparing allylsilane compounds. Background Art

[0002] The construction of complex organosilicon compounds through transition metal-catalyzed C–Si bond formation occupies a very important position in organic synthesis. The silicon-based heteroaromatic structural unit is commonly found in some bioactive organosilicon small molecule compounds, such as P38 MAP Kinase inhibitor, DB-67, Ctopoisomerase inhibitor, GnRH agonist, etc.

[0003]

[0004] The allylation of silanes has always been a challenging research.

[0005] The introduction of an allyl group can change the physical and chemical properties of the original compound. Therefore, the allylation reaction is widely used in the synthesis of organic intermediates and drug molecules. However, traditional transition metal-catalyzed allylation requires strict control of reaction conditions and the use of stoichiometric amounts of reducing agents, which often reduces the functional group tolerance. With the combination of photo- and metal catalysis, these problems have been well solved. The literature reported (Cartwright, K.C.; Tunge, Organophotoredox / palladium dual catalytic decarboxylative Csp 3 –Csp 3 coupling of carboxylicacids and p-electrophiles J.A.Chem.Sci.2020, 11(31), 8167–8175.), and the decarboxylative allylation of carbon was achieved under the dual catalysis of metal and photocatalysis using alkane carboxylic acids, and allylated compounds with complex structures were well constructed, and subsequent functionalization reactions could be carried out. However, this synthesis method has many deficiencies, such as the need to use expensive palladium catalysts and the narrow range of substrates.

[0006] The construction of complex organosilicon compounds through the transition-metal-catalyzed formation of C–Si bonds occupies a very important position in organic synthesis. Organosilicon combines the properties of inorganic and organic materials and has excellent characteristics such as resistance to high and low temperatures, electrical insulation, oxidation resistance, corrosion resistance, non-toxic and odorless, and physiological inertness. The literature has only reported the alkenylation reaction of silanes (Dong, J.; Yuan, X.-A.; Yan, Z.; Mu, L.; Ma, J.; Zhu, C.; Xie, J. Manganese-catalyzed divergent silylation of alkenes. Nat. Chem. 2021, 13(2), 182–190.). By regulating the activity of silicon radicals with ligands, highly selective radical C–Si coupling has been achieved. However, the allylation reaction of silicon has rarely been reported. Summary of the Invention

[0007] The object of the present invention is to provide a method for preparing allylsilane compounds, which does not require the use of expensive noble metal catalysts and photocatalysts, has mild reaction conditions, good substrate universality, and a relatively high reaction yield.

[0008] To achieve the above object, the present invention adopts the following technical scheme:

[0009] A method for preparing allylsilane compounds, using allyl acetate and tert-butyldiphenylsilylformic acid as starting materials, reacting under the conditions of a photocatalyst, a metal catalyst, a ligand, and a base to obtain allylsilane compounds.

[0010] Preferably, the photocatalyst is 2,4,5,6-tetrakis(9H-carbazol-9-yl) isophthalonitrile, the metal catalyst is nickel bromide ethylene glycol dimethyl ether, the ligand is bipyridine, and the base is dipotassium hydrogen phosphate. The reaction formula is:

[0011]

[0012] Preferably, the molar ratio of allyl acetate to tert-butyldiphenylsilylformic acid in the feed is 1:1.5 - 1:3.

[0013] Preferably, the molar ratio of allyl acetate to dipotassium hydrogen phosphate in the feed is 1:0.75 - 1:1.

[0014] Preferably, the molar ratio of 2,4,5,6-tetrakis(9H-carbazol-9-yl) isophthalonitrile in the feed is 1.5% of allyl acetate.

[0015] Preferably, the molar ratio of nickel bromide ethylene glycol dimethyl ether in the feed is 10 - 20% of allyl acetate.

[0016] Preferably, the molar ratio of the bipyridine fed is 12-24% of allyl acetate.

[0017] Preferably, the reaction conditions are as follows: the reaction solvent is ethanol, the reaction light source is blue light, the reaction gas atmosphere is argon, and the reaction time is 18-24 hours.

[0018] Beneficial effects: The preparation method of the allylsilane compound of the present invention does not require the use of expensive noble metal catalysts and photocatalysts, has mild reaction conditions, good substrate generality, and a relatively high reaction yield. Description of the Drawings

[0019] Figure 1 1H NMR spectrum of compound 3 in Example 1; 1

[0020] Figure 2 13C NMR spectrum of the product of compound 3 in Example 1; 13

[0021] Figure 3 1H NMR spectrum of the product of compound 6 in Example 2; 1

[0022] Figure 4 13C NMR spectrum of compound 6 in Example 2; 13

[0023] Figure 5 1H NMR spectrum of the product of compound 7 in Example 2; 1

[0024] Figure 6 13C NMR spectrum of compound 7 in Example 2; 13

[0025] Figure 7 HRMS spectrum of compound 7 in Example 2;

[0026] Figure 8 1H NMR spectrum of the product of compound 10 in Example 3; 1

[0027] Figure 9 13C NMR spectrum of compound 10 in Example 3; 13

[0028] Figure 10 1H NMR spectrum of the product of compound 11 in Example 3; 1

[0029] Figure 11 13C NMR spectrum of compound 11 in Example 3; 13 ​​​​​​​​​​

[0030] Figure 12 It is the HRMS spectrum of Compound 11 in Example 3;

[0031] Figure 13 It is the 1 HNMR spectrum of the product of Compound 13 in Example 4;

[0032] Figure 14 It is the 13 C NMR spectrum of Compound 13 in Example 4;

[0033] Figure 15 It is the 1 HNMR spectrum of the product of Compound 14 in Example 4;

[0034] Figure 16 It is the 13 C NMR spectrum of Compound 14 in Example 4;

[0035] Figure 17 It is the HRMS spectrum of Compound 14 in Example 4. Detailed implementation manners

[0036] The present invention will be further described below in conjunction with examples. The following examples are only used to more clearly illustrate the performance of the present invention and cannot be limited only to the following examples.

[0037] Example 1

[0038] Preparation of Compound 3

[0039] Select two 10 mL Schlenk tubes with magnetic stirrers and side branches, and add Compound 1 (10.1 mg, 0.1 mmol), Compound 2 (42.7 mg, 0.15 mmol), 2,4,5,6-tetrakis(9H-carbazol-9-yl)isophthalonitrile (1.2 mg, 0.0015 mmol, 1.5 mol%), nickel bromide ethylene glycol dimethyl ether (3.1 mg, 0.01 mmol, 10 mol%), bipyridine (1.9 mg, 0.012 mmol, 12 mol%), dipotassium hydrogen phosphate (13.4 mg, 0.075 mmol, 0.75 eq.). And 1.5 mL of absolute ethanol. After purging with argon three times, react at room temperature for 18 hours under blue light irradiation. After the reaction is completed, combine the two reactions, add 5 mL of water, and extract with 5 mL of ethyl acetate three times. Combine the organic phases, add anhydrous magnesium sulfate for drying, evaporate the solvent on a rotary evaporator, and then obtain Compound 3 (46.6 mg, 82%) through flash silica gel column chromatography (eluent: petroleum ether). The reaction formula is as follows:

[0040]

[0041] The product structure characterization data are as follows:

[0042] 1 H NMR (400 MHz, CDCl3) δ 7.66 (dd, J = 7.6, 1.6 Hz, 4H), 7.45–7.35 (m, 6H), 5.88–5.76 (m, 1H), 4.95 (d, J = 15.3 Hz, 1H), 4.85 (d, J = 9.2 Hz, 1H), 2.24 (d, J = 7.9 Hz, 2H), 1.11 (s, 9H) ppm. As Figure 1 。

[0043] 13 C NMR (101 MHz, CDCl3) δ 136.0, 134.7, 134.4, 129.2, 127.5, 114.5, 27.9, 18.8, 18.5 ppm. As Figure 2 。

[0044] Example 2

[0045] 1) Preparation of Compound 5

[0046] Select a 50 mL Schlenk tube with a magnetic stir bar and a side arm. Connect a constant pressure dropping funnel to the mouth of the tube. After sealing the reaction tube, evacuate and refill with nitrogen three times at the side arm. Under a nitrogen atmosphere, add n-decanal 4 (0.7814 g, 5 mmol) to the Schlenk tube, then inject 10 mL of anhydrous tetrahydrofuran with a syringe. Start magnetic stirring. After dissolution, place it in an ice bath. When cooled to 0 °C, add 7.5 mL of a 1.0 mol / L solution of vinylmagnesium bromide in tetrahydrofuran (concentration: 1.0 mol / L, 1.5 equivalents) dropwise to the constant pressure dropping funnel with a syringe equipped with a needle. Slowly add the vinylmagnesium bromide solution in tetrahydrofuran to the Schlenk tube under ice bath conditions. After addition, remove the ice bath and react at room temperature (25 °C). After 8 hours, add 20 mL of saturated ammonium chloride solution, then add 10 mL of ethyl acetate and extract 3 times. Combine the organic phases and remove the solvent by rotary evaporator to obtain crude product 5. Without purification, directly proceed to the next step. The reaction formula is as follows:

[0047]

[0048] 2) Preparation of Compound 6

[0049] Select a 50 mL Schlenk tube with a magnetic stir bar and a side arm. Connect a constant pressure dropping funnel to the mouth of the tube. After sealing the reaction tube, evacuate and refill with nitrogen three times at the side arm, and then add 4-dimethylaminopyridine (244.4 mg, 2 mmol, 40 mol%) to the Schlenk tube under a nitrogen atmosphere. Add the crude product 5, 3.0357 g of triethylamine (30 mmol, 6 equivalents), and then add 10 mL of dichloromethane. Turn on the magnetic stirrer. After dissolution, slowly add acetic anhydride (2.0458 g, 20 mmol, 4 equivalents) using a syringe with a needle. After the addition is complete at room temperature (25 °C), react the mixture at 40 °C for 8 hours. Then add 20 mL of saturated sodium carbonate solution, and extract with 10 mL of ethyl acetate three times. After combining the organic phases, remove the solvent using a rotary evaporator, and then perform flash silica gel column chromatography (eluent: petroleum ether:ethyl acetate volume ratio = 20:1) to obtain compound 6 (827.7 mg, 73%). The reaction formula is as follows:

[0050]

[0051] The structure characterization data of the product is as follows:

[0052] 1 H NMR (400 MHz, CDCl3) δ 5.79–5.69 (m, 1H), 5.23–5.16 (m, 2H), 5.12 (d, J =

[0053] 10.5 Hz, 1H), 2.03 (s, 3H), 1.55 (tt, J = 14.4, 7.0 Hz, 2H), 1.25 (d, J = 7.6 Hz, 14H), 0.85 (t, J = 6.8 Hz, 3H) ppm. As Figure 3 。

[0054] 13 C NMR (101 MHz, CDCl3) δ 170.27, 136.62, 116.40, 74.82, 34.15, 31.83, 29.46, 25.01, 22.62, 21.17, 14.04 ppm. As Figure 4 。

[0055] 3) Preparation of compound 7

[0056] Select two 10 mL Schlenk tubes with magnetic stirrers and side arms, and add compound 6 (22.7 mg, 0.1 mmol), compound 2 (42.7 mg, 0.15 mmol), 2,4,5,6-tetrakis(9H-carbazol-9-yl) isophthalonitrile (1.2 mg, 0.0015 mmol, 1.5 mol%), nickel(II) bromide ethylene glycol dimethyl ether complex (3.1 mg, 0.01 mmol, 10 mol%), 2,2'-bipyridine (1.9 mg, 0.012 mmol, 12 mol%), dipotassium hydrogen phosphate (13.4 mg, 0.075 mmol, 0.75 eq.), and 1.5 mL of anhydrous ethanol. After purging with argon three times, the reaction is carried out at room temperature under blue light irradiation for 18 hours. After the reaction is completed, the two reactions are combined, 5 mL of water is added, and then extracted with 5 mL of ethyl acetate three times. The combined organic phases are dried over anhydrous magnesium sulfate, and the solvent is removed by rotary evaporation. Then, compound 7 (69.9 mg, 86%) is obtained by flash silica gel column chromatography (eluent: petroleum ether). The reaction formula is as follows:

[0057]

[0058] The product structure characterization data are as follows:

[0059] 1 H NMR (400 MHz, CDCl3) δ 7.71–7.62 (m, 4H), 7.39 (tt, J = 7.9, 4.5 Hz, 6H), 5.46–5.37 (m, 1H), 5.37–5.24 (m, 1H), 2.14 (d, J = 6.7 Hz, 2H), 1.90 (dq, J = 13.5, 6.9 Hz, 2H), 1.36–1.10 (m, 14H), 1.12 (s, 4.5H), 1.10 (s, 4.5H), 0.94–0.90 (m, 3H) ppm. As Figure 5 。

[0060] 13 C NMR (101 MHz, CDCl3) δ 136.02, 135.99, 134.8, 134.7, 130.9, 129.2, 129.0, 128.9, 127.5, 127.4, 125.3, 124.4, 32.7, 31.9, 29.7, 29.62, 29.58, 29.54, 29.46, 29.43, 29.36, 29.35, 29.1, 27.92, 27.90, 27.2, 22.7, 18.4, 16.8, 14.1, 12.2 ppm. As Figure 6 。

[0061] HRMS (ESI): [M+Na] +Calculated for C 28 H 42 NaSi + 429.2948, found: 429.2963. As Figure 7 。

[0062] Example 3

[0063] 1) Preparation of Compound 9

[0064] Select a 50 mL Schlenk tube with a magnetic stir bar and a side arm. Connect a constant pressure dropping funnel to the mouth of the tube. After sealing the reaction tube, evacuate and refill with nitrogen three times at the side arm. Under a nitrogen atmosphere, add cyclohexyl formaldehyde 8 (0.4908 g, 5 mmol) to the Schlenk tube, then inject 10 mL of anhydrous tetrahydrofuran with a syringe. Turn on the magnetic stirrer, dissolve the mixture, and place it in an ice bath. After cooling to 0 °C, slowly add 7.5 mL of 1.0 mol / L ethylene magnesium bromide in tetrahydrofuran solution (concentration 1.0 mol / L, 1.5 equivalents) dropwise from the constant pressure dropping funnel with a syringe equipped with a needle into the Schlenk tube under ice bath conditions. After adding, remove the ice bath and let the reaction proceed at room temperature (25 °C). After 8 hours, add 20 mL of saturated ammonium chloride solution, then extract three times with 10 mL of ethyl acetate. Combine the organic phases, remove the solvent by rotary evaporation to obtain the crude product 9, which can be directly used for the next step without purification. The reaction equation is as follows:

[0065]

[0066] 2) Preparation of Compound 10

[0067] Select a 50 mL Schlenk tube with a magnetic stir bar and a side arm. Connect a constant pressure dropping funnel to the mouth of the tube. After sealing the reaction tube, evacuate and refill with nitrogen three times at the side arm. Under a nitrogen atmosphere, add 4-dimethylaminopyridine (244.4 mg, 2 mmol, 40 mol%) and the crude product 9 to the Schlenk tube, followed by triethylamine (3.0357 g, 30 mmol, 6 equivalents). Then add 10 mL of dichloromethane. Turn on the magnetic stirrer, dissolve the mixture, and slowly add acetic anhydride (2.0458 g, 20 mmol, 4 equivalents) dropwise with a syringe equipped with a needle. After the addition is complete at room temperature (25 °C), let the reaction proceed at 40 °C for 8 hours. Then add 20 mL of saturated sodium carbonate solution, extract three times with 10 mL of ethyl acetate, combine the organic phases, remove the solvent by rotary evaporation, and perform flash silica gel column chromatography (eluent: petroleum ether:ethyl acetate volume ratio = 20:1) to obtain Compound 10 (402.4 mg, 48%). The reaction equation is as follows:

[0068]

[0069] The product structure characterization data are as follows:

[0070] 1 H NMR (400 MHz, CDCl3) δ 5.76 (ddd, J = 17.2, 10.5, 6.7 Hz, 1H), 5.25–5.08 (m, 3H), 2.14–2.06 (m, 1H), 2.05 (s, 3H), 1.73–1.48 (m, 6H), 1.27 (ddd, J = 23.0, 9.3, 4.1 Hz, 2H) ppm. As Figure 8 。 13 C NMR (101 MHz, CDCl3) δ 170.4, 116.9, 78.3, 43.4, 28.7, 28.6, 25.5, 25.3, 21.2 ppm. As Figure 9 。

[0071] 3) Preparation of Compound 11

[0072]

[0073] Select two 10 mL Schlenk tubes with magnetic stirrers and branches, and add compound 10 (16.9 mg, 0.1 mmol), compound 2 (42.7 mg, 0.15 mmol), 2,4,5,6 - tetra(9H - carbazol - 9 - yl) isophthalonitrile (1.2 mg, 0.0015 mmol, 1.5 mol%), nickel(II) bromide - ethylene glycol dimethyl ether complex (3.1 mg, 0.01 mmol, 10 mol%), 2,2'-bipyridine (1.9 mg, 0.012 mmol, 12 mol%), dipotassium hydrogen phosphate (13.4 mg, 0.075 mmol, 0.75 eq.), and 1.5 mL of absolute ethanol. After evacuating and back - filling with argon three times, react at room temperature under blue light irradiation for 18 hours. After the reaction is completed, combine the two reactions, add 5 mL of water, extract with 5 mL of ethyl acetate three times, combine the organic phases, dry over anhydrous magnesium sulfate, remove the solvent by rotary evaporation on a rotary evaporator, and then obtain compound 11 (69.9 mg, 72%) by flash silica gel column chromatography (eluent: petroleum ether). The reaction formula is as follows:

[0074]

[0075] The product structure characterization data are as follows:

[0076] 11H NMR (400 MHz, CDCl3) δ 7.68–7.64 (m, 4H), 7.48–7.32 (m, 6H), 5.45–5.35 (m, 1H), 5.32–5.17 (m, 1H), 2.71–2.64 (m, 0.5H), 2.33–2.27 (m, 0.5H), 2.20 (dd, J = 8.1, 1.4 Hz, 1H), 2.15 (d, J = 7.6 Hz, 1H), 1.68–1.46 (m, 6H), 1.12 (d, J = 5.8 Hz, 11H) ppm. As Figure 10 。

[0077] 13 13C NMR (101 MHz, CDCl3) δ 136.04, 136.01, 135.5, 134.8, 134.7, 134.5, 129.0, 128.9, 127.44, 127.40, 123.4, 123.0, 43.5, 38.1, 33.4, 33.1, 27.93, 27.91, 25.4, 25.0, 18.4, 16.9, 12.3 ppm. As Figure 11 。

[0078] HRMS (ESI): [M+Na] + calcd for C 24 H 32 NaSi + 371.2165, found: 371.2176. As Figure 12 。

[0079] Example 4

[0080] 1) Preparation of Compound 13

[0081] Select a 50 mL Schlenk tube with a magnetic stir bar and a side arm. Connect a constant pressure dropping funnel to the mouth of the tube. After sealing the reaction tube, evacuate and replace the gas with nitrogen three times at the side arm opening. Under a nitrogen atmosphere, add 4-dimethylaminopyridine (146.7 mg, 1.2 mmol, 40 mol%), isophytol 12 (889.6 mg, 3 mmol), and triethylamine (1.8215 g, 18 mmol, 6 equiv) to the Schlenk tube. Then add 10 mL of dichloromethane. Start magnetic stirring. After dissolution, slowly add acetic anhydride (1.2275 g, 12 mmol, 4 equiv) using a syringe with a needle. After the addition is complete at room temperature (25 °C), react the mixture at 40 °C for 8 hours. Then add 20 mL of saturated sodium carbonate solution, and extract with 10 mL of ethyl acetate three times. Combine the organic phases, remove the solvent by rotary evaporation, and then perform flash silica gel column chromatography (eluent: petroleum ether:ethyl acetate volume ratio = 20:1) to obtain compound 13 (577.0 mg, 57%). The reaction formula is as follows:

[0082]

[0083] The structure characterization data of the product is as follows:

[0084] 1 H NMR (400 MHz, CDCl3) δ 5.96 (dd, J = 17.5, 10.9 Hz, 1H), 5.16–5.07 (m, 2H), 1.99 (s, 3H), 1.85–1.69 (m, 2H), 1.51 (s, 4H), 1.35 (dd, J = 11.2, 4.1 Hz, 2H), 1.24 (dtd, J = 15.2, 7.6, 4.5 Hz, 10H), 1.14–1.02 (m, 6H), 0.85 (dd, J = 9.7, 6.6 Hz, 12H) ppm. As Figure 13 。

[0085] 13 C NMR (101 MHz, CDCl3) δ 169.9, 142.0, 112.9, 83.1, 40.1, 39.35, 37.37, 37.26, 37.23, 37.1, 32.8, 28.0, 24.8, 24.4, 23.5, 22.7, 22.6, 22.1, 21.0, 19.7, 19.66, 19.62, 19.55 ppm. As Figure 14 。

[0086] 2) Preparation of compound 14

[0087] Select two 10 mL Schlenk tubes with magnetic stirrers and side arms, and add Compound 13 (33.9 mg, 0.1 mmol), Compound 2 (85.4 mg, 0.3 mmol), 2,4,5,6-tetrakis(9H-carbazol-9-yl) isophthalonitrile (2.4 mg, 0.003 mmol, 3.0 mol%), nickel(II) bromide ethylene glycol dimethyl ether complex (6.2 mg, 0.02 mmol, 20 mol%), 2,2'-bipyridine (3.8 mg, 0.024 mmol, 24 mol%), dipotassium hydrogen phosphate (17.5 mg, 0.01 mmol, 1.0 eq.), and 1.5 mL of anhydrous ethanol. After purging with argon three times, the reaction is carried out at room temperature under blue light irradiation for 18 hours. After the reaction is completed, the two reactions are combined, 5 mL of water is added, and then extracted with 5 mL of ethyl acetate three times. The combined organic phases are dried over anhydrous magnesium sulfate, and the solvent is removed by rotary evaporation. Compound 14 (75.3 mg, 73%) can be obtained by flash silica gel column chromatography (eluent: petroleum ether). The reaction formula is as follows:

[0088]

[0089] The product structure characterization data are as follows:

[0090] 1 H NMR (400 MHz, Chloroform-d) δ 7.69–7.60 (m, 4H), 7.41–7.33 (m, 6H), 5.18 (q, J = 7.5 Hz, 1H), 2.06 (d, J = 7.9 Hz, 2H), 1.84 (q, J = 6.9 Hz, 2H), 1.56 (d, J = 7.2 Hz, 3H), 1.34–1.22 (m, 10H), 1.20–1.13 (m, 4H), 1.10–1.04 (m, 12H), 0.90–0.85 (m, 12H), 0.79 (d, J = 6.6 Hz, 2H) ppm. As Figure 15 。

[0091] 13 C NMR (101 MHz, CDCl3) δ 136.0, 135.7, 135.0, 134.6, 134.2, 129.4, 128.9, 127.8, 127.4, 119.4, 119.1, 40.3, 39.4, 37.4, 37.3, 36.8, 36.7, 32.8, 32.7, 31.8, 28.0, 27.5, 25.5, 24.8, 24.8, 23.3, 22.7, 22.6, 19.8, 19.7, 18.4, 15.8, 12.4, 12.0 ppm. (Specification drawing - Figure 16 )

[0092] HRMS(ESI): [M+Na] + calcd for C 36 H 58 NaSi + 541.4200, found: 541.4253. As Figure 17 。

[0093] The above are only the preferred embodiments of the present invention. It should be pointed out that for those of ordinary skill in the art, without departing from the principle of the present invention, several improvements and modifications can be made, and these improvements and modifications should also be regarded as the protection scope of the present invention.

Claims

1. A method for preparing allylsilane compounds, characterized in that: Comprising the following steps: Using allyl acetate and tert-butyl diphenylsilylformic acid as starting materials, reacting under the conditions of a photocatalyst, a metal catalyst, a ligand, and a base to obtain allylsilane compounds; The photocatalyst is 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile, the metal catalyst is nickel bromide ethylene glycol dimethyl ether, the ligand is bipyridine, and the base is dipotassium hydrogen phosphate. The reaction formula is:

2. The preparation method of the allylsilane compound according to claim 1, characterized in that: The molar ratio of allyl acetate to tert-butyl diphenylsilylformic acid in the feed is 1:1.5 - 1:

3.

3. The preparation method of the allylsilane compound according to claim 1, characterized in that: The molar ratio of allyl acetate to dipotassium hydrogen phosphate in the feed is 1:0.75 - 1:

1.

4. The preparation method of the allylsilane compound according to claim 1, characterized in that: The molar ratio of 2,4,5,6-tetra(9H-carbazol-9-yl)isophthalonitrile in the feed is 1.5% of allyl acetate.

5. The preparation method of the allylsilane compound according to claim 1, characterized in that: The molar ratio of nickel bromide ethylene glycol dimethyl ether in the feed is 10 - 20% of allyl acetate.

6. The preparation method of the allylsilane compound according to claim 1, wherein: The molar ratio of bipyridine in the feed is 12 - 24% of allyl acetate.

7. The method for preparing allylsilane compounds according to claim 1, wherein: The conditions of the reaction are: the reaction solvent is ethanol, the reaction light source is blue light, the reaction gas atmosphere is argon, and the reaction time is 18 - 24 hours.

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