Synthesis method of diaryl methylsilane compound

Abstract

The invention belongs to the field of organic synthesis, and particularly relates to a synthetic method of a diaryl methylsilane compound. In an inert gas environment, benzylsilane compounds as shown in formulae 1 and 4 and aryl halides (R7 = Br, 1) as shown in formulae 2 and 5 are mixed and heated with isopropyl ether in the presence of an allyl palladium (II) chloride dipolymer, 4, 6-di (diphenylphosphine) phenazine and bis (trimethylsilyl) caesium amine to synthesize the diaryl methylsilane compounds as shown in formulae 3 and 6. According to the invention, the coupling reaction of the benzyl silane compound and the aryl halide is realized by adopting a catalytic amount of the allyl chloride palladium (II) dimer, and the palladium catalyst shows obvious catalytic performance.

Description

Technical Field

[0001] The invention belongs to the field of organic synthesis and proposes a method for synthesizing a series of diarylmethylsilane compounds through a cross-coupling reaction of benzylsilane and aryl halide. Background Art

[0002] Alkylsilanes have a wide range of applications in drug design, materials development, and organic synthesis. These compounds are not only promising ligands in alkyne metathesis reactions but also common substrates for Hiyama cross-coupling reactions, enabling the construction of a variety of complex molecular structures. Their unique structural characteristics and versatile reactivity have attracted widespread attention from organic chemists. Traditional methods for synthesizing silanes include cross-coupling reactions between Grignard reagents and alkyl bromides, cross-coupling reactions between metal reagents and silicified chlorosilanes, and coupling reactions between alkyl electrophiles and prefunctionalized silicon-containing nucleophiles. However, these methods typically require the pre-preparation of organometallic reagents and have a limited substrate range. Therefore, the development of novel and efficient methods for the synthesis of diarylbenzylsilanes is of great significance and value. Summary of the Invention

[0003] The present invention provides a Pd / Nixantphos-catalyzed cross-coupling reaction between benzylsilane and aryl halide to synthesize a series of diarylmethylsilanes. This synthesis method achieves chemoselective deprotonation of benzylsilane at the benzylic position using the rarely used CsN(SiMe3)2, providing a highly efficient, direct, mild, and simple method. The specific scheme is as follows:

[0004]

[0005] A method for synthesizing diarylmethylsilane compounds comprises: using benzylsilane compounds represented by formulas 1 and 4 and aryl halides (R7=Br, I) represented by formulas 2 and 5, in the presence of allylpalladium chloride (ID) dimer, 4,6-bis(diphenylphosphino)phenazine, and cesium bistrimethylsilylamino in an inert gas environment, mixing with isopropyl ether and heating to synthesize diarylmethylsilane compounds represented by formulas 3 and 6;

[0006] where R 1 Any one selected from methyl and ethyl; R 2 Any one selected from methyl, ethyl, and phenyl; R 3 Any one selected from methyl, ethyl, and n-propyl: R 4 Any one selected from hydrogen, chlorine, and trimethylsilyl; R 5 Any one selected from hydrogen and methyl; R 6Any one selected from hydrogen, methyl, isopropyl; R 7 Any one selected from bromine and iodine.

[0007] The method of the present invention uses a catalytic amount of transition metal to achieve efficient synthesis of diarylmethylsilane compounds under mild reaction conditions; the aryl halide used in the synthesis method is cheap and easy to obtain; R 1 、R 2 、R 3 、R 4 、R 5 、R 6 There are multiple options available, making it more applicable.

[0008] Preferably, the reaction is carried out under the protection of an inert gas, and preferably, the inert gas is nitrogen.

[0009] Preferably, the synthesis occurs in the presence of a transition metal catalyst, a phosphine ligand, an amide base and an organic solvent.

[0010] Preferably, the transition metal catalyst is a palladium catalyst; the phosphine ligand is 4,6-bis(diphenylphosphino)phenazine; and the amide base is cesium bistrimethylsilylamido.

[0011] Preferably, the palladium catalyst is allylpalladium (II) chloride dimer.

[0012] Preferably, the organic solvent is isopropyl ether.

[0013] Preferably, the reaction temperature is 40°C.

[0014] Preferably, the method of the present invention can be used to synthesize diarylmethylsilane compounds with the following structure:

[0015]

[0016]

[0017] Benzylsilane compounds and aryl halides are reacted in the presence of a catalytic amount of allylpalladium (II) chloride dimer, 4,6-bis(diphenylphosphino)phenazine and an equivalent amount of cesium bistrimethylsilylamino with an organic solvent of isopropyl ether to finally synthesize diarylmethylsilane compounds.

[0018] The technical solution of the present invention can achieve at least one of the following beneficial effects:

[0019] The raw materials 1 and 4 used in the synthesis method of the present invention are easy to prepare, and the raw materials 2 and 5 are cheap and easily available;

[0020] The operation steps required by the present invention are relatively simple, and no extreme heating or cooling is required. The reaction can be performed at normal pressure, which is safe and convenient.

[0021] R in the present invention 1 、R 2 、R 3 、R 4 、R 5 、R 6 and aryl halides can be selected from a variety of options, so the substrate of the present invention has a wider applicability and can be used to synthesize various diarylmethylsilane compounds;

[0022] Compared with traditional methods, the method of the present invention has many advantages such as high yield, mild conditions, simple operation, etc. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] The accompanying drawings are hydrogen and carbon nuclear magnetic resonance spectra of the products of each embodiment. The serial numbers of the accompanying drawings correspond to the serial numbers of the embodiments. Figure A is a hydrogen nuclear magnetic resonance spectrum, and Figure B is a carbon nuclear magnetic resonance spectrum. Figure 1A is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 1, Figure 1B is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 1; Figure 2A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 2, Figure 2B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 2; Figure 3A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 3, Figure 3B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 3; Figure 4A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 4, Figure 4B is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 4; Figure 5A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 5, Figure 5B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 5; Figure 6A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 6, Figure 6B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 6; Figure 7A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 7, Figure 7B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 7; Figure 8A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 8, Figure 8B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 8; Figure 9A This is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 9, Figure 9B This is the carbon nuclear magnetic resonance spectrum of the product obtained in Example 9; Figure 10A is the hydrogen nuclear magnetic resonance spectrum of the product obtained in Example 10, Figure 10BThe carbon nuclear magnetic resonance spectrum of the product obtained in Example 10 is shown in FIG. Specific embodiments

[0024] For the convenience of those skilled in the art to understand, the concept of the present invention is further described below in conjunction with the embodiments. The specific description of the following examples is not a limitation of the present invention, but is only for the convenience of those skilled in the art to understand the technical solution. The various raw materials involved in the description are all purchased from the market, or through simple synthesis, other medicines etc. are purchased from Anaiji, Bi De, Sigma-Aldrich, Acros, Alfa Aesar, Adamas-beta or J&K., and the nuclear magnetic resonance spectrometer model is Bruker 400M.

[0025] Example 1

[0026] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltrimethylsilane (16.4 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (20.4 mg, 85% yield) as a white solid. 1 H NMR (400MHz, CDCl3) δ: 7.25-7.22 (m, 8H), 7, 12-7.08 (m, 2H), 3.50 (s, 1H), 0.02 (s, 9H)ppm. 13 C{ 1 H}NMR (101MHz, CDDCl3) δ: 142.9, 128.8, 123.4, 125.1, 446.2, 4.6ppm.

[0027] The raw materials in Example 1 were changed. The following 10 experimental examples were designed, of which the first experiment is Example 1, and the corresponding product NMR spectrum is shown in Figure 1. The NMR spectra of the remaining 2-10 groups of products are numbered corresponding to the corresponding examples.

[0028] The table lists the structural formulas of the products in Examples 1-10, and the last column lists the yields of the products in each Example, and indicates the specific implementation conditions of each Example. The specific meanings of the implementation conditions of each Example are shown below the table.

[0029]

[0030]

[0031] Example 2

[0032] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), 4-(trimethylsilyl)benzyltrimethylsilane (23.7 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (23.4 mg, 75% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.54-7.51 (m, 2H), 7.38-7.32 (m, 7H), 3.62 (s, 1H), 0.35 (s, 9H), 0.16 (s, 9H)ppm. 13 C{ 1 H}NMR (101MHz, CDCl3) δ: 142.8, 142.1, 135.5, 132.6, 128.1, 127.6, 127.4, 124.3, 45.5, -1.7, -2.4ppm.

[0033] Example 3

[0034] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), 4-chlorobenzyltrimethylsilane (19.9 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (20.1 mg, 73% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.31-7.24 (m, 3H), 7.23-7.15 (m, 6H), 3.51 (s, 1H), 0.05 (s, 9H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 142.5, 141.6, 130.9, 130.0, 128.8, 128.6, 128.5, 125.4, 45.5, -1.6ppm.

[0035] Example 4

[0036] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( iPr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltriethylsilane (20.6 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to obtain the product (22.6 mg, 80% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.25-7.21 (m, 8H), 7.13-7.08 (m, 2H), 3.63 (s, 1H), 0.85-0.81 (m, 9H), 0.62-0.55 (m, 6H)ppm. 13 C NMR (101MHz, Chloroform-d) δ142.9, 128.9, 128.3, 125.1, 43.0, 7.6, 3.4ppm.

[0037] Example 5

[0038] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2· (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyldimethylpropylsilane (19.2 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3 × 1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to obtain the product (20.1 mg, 75% yield) as a colorless liquid. 1H NMR (400MHz, CDCl3) δ: 7.26-7.22(m 8H), 7.16-7.10 (m, 2H), 3.53 (s, 1H), 1.28-1.21 (m, 2H), 0.88 (t, J = 7.2Hz, 3H), 0.55-0.48 (m, 2H), 0.02 (s, 6H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 143.0, 128.9, 128.4, 125.1, 45.4, 18.4, 17.4, 17.3-3.3ppm.

[0039] Example 6

[0040] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyldimethylphenylsilane (22.6 mg, 0.1 mmol, 1.0 equiv) and iodobenzene (40.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (17.2 mg, 57% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.37-7.32 (m, 1H), 7.29-7.27 (m, 4H), 7.22-7.18 (m, 4H), 7.14-7.11 (m, 6H), 3.74 (s, 1H), 0.29 (s, 6H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 142.3, 137.6, 134.5, 129.2, 129.0, 128.3, 127.6, 125.3, 45.8, -3.1ppm.

[0041] Example 7

[0042] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( i Pr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltrimethylsilane (16.4 mg, 0.1 mmol, 1.0 equiv) and 4-methyliodobenzene (43.6 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (17.3 mg, 68% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.27-7.21 (m, 4H), 7.15-7.09 (m, 3H), 7.08-7.04 (m, 2H), 3.47 (s, 1H), 2.29 (s, 3H), 0.03 (s, 9H) ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 143.3, 139.9, 134.6, 129.1, 128.8, 128.7, 128.3, 125.0, 45.6, 21.0, -1.6ppm.

[0043] Example 8

[0044] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( iPr2o) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltrimethylsilane (16.4 mg, 0.1 mmol, 1.0 equiv) and 4-isopropyliodobenzene (49.2 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (23.4 mg, 83% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.28-7.26 (m, 4H), 7.22-7.19 (m, 2H), 7.17-7.13 (m, 3H ), 3.52 (s, 1H), 2.89 (p, J = 6.9Hz, 1H), 1.26 (d, J = 6.9Hz, 6H), 0.07 (s, 9H) ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 145.5, 143.4, 140.2, 128.8, 128.7, 128.4, 126.4, 125.1, 45.8, 33.7, 24.2, -1.5ppm.

[0045] Example 9

[0046] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( iPr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltrimethylsilane (16.4 mg, 0.1 mmol, 1.0 equiv) and 3-methyliodobenzene (43.6 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (15.5 mg, 61% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 7.29-7.26 (m, 1H), 7.25-7.22 (m, 3H), 7.16-7.11 (m, 2H), 7.08-7.04(m, 2H), 6.97-6.94(m, 1H), 3.48(s, 1H), 2.32(s, 3H), 0.05(s, 9H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 143.1, 142.9, 137.8, 129.8, 128.8, 128.4, 128.2, 125.9, 125.8, 125.1, 46.1, 21.7, -1.6ppm.

[0047] Example 10

[0048] Under nitrogen atmosphere in a glove box, [PdCl(allyl)]2 (3.3 mg, 9 mol%) and Nixantphos (7.7 mg, 14 mol%) were placed in a dry microwave tube (10 mL) equipped with a magnet. Next, 0.5 mL of isopropyl ether ( iPr2O) and added it to a microwave tube. The resulting solution was stirred at room temperature for 1 hour. CsN(SiMe3)2 (88.6 mg, 3.0 equiv), benzyltrimethylsilane (16.4 mg, 0.1 mmol, 1.0 equiv) and 1-naphthoiodobenzene (50.8 mg, 0.2 mmol, 2.0 equiv) were then added to the reaction flask. The microwave tube was sealed with a lid and removed from the glove box. The reaction mixture was stirred in an oil bath at 40°C for 12 hours. After the reaction was completed, the lid of the microwave tube was opened and exposed to air, and then three drops of water were slowly added to quench the reaction. The reaction mixture was passed through a short pad of silica and washed with an additional 3 mL of ethyl acetate (3×1 mL), and the combined solution was concentrated under reduced pressure. The crude product was purified by flash chromatography on a silica column (eluted with petroleum ether) to give the product (22.7 mg, 78% yield) as a colorless liquid. 1 H NMR (400MHz, CDCl3) δ: 8.13-8.09 (m, 1H), 7.82-7.79 (m, 1H), 7.72-7.69 (m, 1H), 7.58 (dd, J = 7.2, 1 .2Hz, 1H), 7.46-7.39(m, 3H), 7.21-7.17(m, 4H), 7.08-7.04(m, 1H), 4.31(s, 1H), 0.12(s, 9H)ppm. 13 C{ 1 H} NMR (101MHz, CDCl3) δ: 143.1, 138.9, 134.5, 133.0, 128.9, 128.4, 128.2, 127.3, 126.6, 125.9, 125.4, 125.2, 124.9, 124.3, 40.4, -1.1ppm.

Claims

1. A method for synthesizing a diarylmethylsilane compound, characterized in that: In an inert gas environment, benzylsilane compounds shown in formula 1 and 4 and aryl halides shown in formula 2 and 5 (R 7 =Br, I) in the presence of allylpalladium (II) chloride dimer, 4,6-bis(diphenylphosphino)phenazine and cesium bistrimethylsilylamino, mixed with isopropyl ether and heated to synthesize diarylmethylsilane compounds shown in formulas 3 and 6; where R 1 Any one selected from methyl and ethyl; R 2 Any one selected from methyl, ethyl, and phenyl; R 3 Any one selected from methyl, ethyl, and n-propyl; R 4 Any one selected from hydrogen, chlorine, and trimethylsilyl; R 5 Any one selected from hydrogen and methyl; R 6 Any one selected from hydrogen, methyl, isopropyl; R 7 Any one selected from bromine and iodine.

2. The synthesis method according to claim 1, characterized in that The inert gas is nitrogen.

3. The synthesis method according to claim 1, wherein The reaction temperature was 40°C.

4. The synthesis method according to claim 1, characterized in that The benzylsilane compounds, aryl halides and the product diarylmethylsilane compounds are as shown in the following table:

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