Process for the preparation of aryltrimethylstannane compounds

Abstract

The application discloses a preparation method of aryl trimethyl tin alkylate, which comprises the following steps: uniformly mixing aryl halide, 2,4,5,6-tetrakis(9-carbazolyl)-m-dinitrile, N,N-diisopropylethylamine, hexamethyldistannane and a solvent, carrying out reaction, and removing the solvent after the reaction is completed; then carrying out column chromatography to obtain pure aryl trimethyl tin alkylate; the reaction method of tin alkylation has good tolerance and universality to functional groups, the yield of the prepared aryl trimethyl tin alkylate is high, and the highest yield can reach 95%. The raw material adopted is cheap, stable, environment-friendly, low-toxic and the like, and is widely available, cheap and easy to obtain, and has low production cost.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of organic synthesis, and particularly relates to a preparation method of aryltrimethylstannane compounds. BACKGROUND

[0002] Aryltrimethylstannane is one of the most widely used small organic molecules in arylstannane compounds. Because it is an important reaction substrate for the construction of carbon-carbon bonds and carbon-heteroatom bonds, it is widely used in organic synthesis, medicinal chemistry and material chemistry, and plays an important role in the synthesis of bioactive molecules and natural products. In organic synthesis, aryltrimethylstannane as a reaction substrate participates in Stille coupling reaction to realize functional group transformation to construct desired compounds; in industrial synthesis, aryltrimethylstannane is often used to synthesize luminescent molecular materials.

[0003] For a long time, people have been seeking a simple and convenient method for synthesizing aryltrimethylstannane compounds. The known synthesis methods are still very limited, mainly including the following two methods: 1. Starting from aryl halide, aryl Grignard reagent or aryl lithium reagent is prepared, and then reacted with trimethyltin halide to obtain aryltrimethylstannane; 2. Aryl iodide or bromide is reacted with hexamethyldistannane under the action of expensive palladium catalyst or nickel catalyst to obtain aryltrimethylstannane.

[0004] The disadvantages of the above methods are: (1) The raw material is complex, and the synthesis starts from the preparation of aryl Grignard reagent, and the functional group tolerance of organometallic reagent is very poor. (2) The use of noble metal catalysts is economically poor, and the cost is high, and high temperature is usually required. (3) It is not environmentally friendly, and the operation is complex, and both methods require harsh reaction conditions. SUMMARY

[0005] The purpose of the present application is to provide a visible light catalytic tin reaction method of aryl halide, which has strong substrate universality and high functional group tolerance, and can synthesize various aryltrimethylstannanes (Ar-SnMe3) with different substituents.

[0006] Another purpose of the present application is to provide an aryltrimethylstannane which can be prepared by the tin reaction method.

[0007] The technical scheme of the present application is as follows:

[0008] The aryl halide, 2,4,5,6-tetrakis(9-carbazolyl)-m-benzene dicarbonitrile, N,N-diisopropylethylamine and hexamethyldistannane are mixed in an organic solvent and reacted under the catalysis of visible light, and the reaction formula is as follows:

[0009] +(SnMe3)2

[0010] =Ar,

[0011] After the reaction is completed, the solvent is removed by concentration, and then column chromatography is performed to obtain the pure aryl trimethyl tin compound.

[0012] The aryl halide has a general structure of Ar-X, wherein Ar is a phenyl group or an aromatic heterocyclic group, and X is a halogen atom. wherein Me is a methyl group.

[0013] Further, when Ar is a phenyl group, R is a methylsulfonyl group, an acetoxy group, a cyano group, a methoxy group, an alkynyl group, or a hydroxymethyl group.

[0014] Further, when Ar is an aromatic heterocyclic group, the aromatic heterocyclic group is a benzene ring, a naphthalene ring, an anthracene ring, or a pyridine ring.

[0015] Further, the aryl halide is 4-iodobenzyl alcohol, 1-iodo-4-methylsulfonylbenzene, 4-iodoacetylphenol, (4-iodophenyl ethynyl)trimethylsilane, 4-(pyrrolinylcarbonyl) bromobenzene, 3-bromoanisole, 1-iodo-3,4-methylenedioxybenzene, 5-iodo potassium cyanide, 2-iodonaphthalene, or 2-iodoanthracene-9,10-dione.

[0016] Further, the aryl trimethyl tin compound is (4-(trimethyltin)phenyl)methanol, (4-(methylsulfonyl)phenyl)trimethyltin, 4-(trimethyltin)phenyl acetate, ((4-(trimethyltin)phenyl)ethynyl)trimethylsilane, pyrrolidin-1-yl(4-(trimethyltin)phenyl)methanone, (3-methoxyphenyl)trimethyltin, benzo[d][1,3]dioxol-5-yltrimethyltin, 5-(trimethyltin)nicotinonitrile, (naphthalen-2-yl)trimethyltin, or 2-(trimethyltin)anthracene-9,10-dione.

[0017] Further, the aryl halide, 2,4,5,6-tetra(9-carbazolyl)-1,3-dicyanobenzene, N,N-diisopropylethylamine, and hexamethylditin have a mass ratio of 1: (0.01-0.03): 1: (1-2).

[0018] Further, the mobile phase in the column chromatography is petroleum ether and / or ethyl acetate.

[0019] Further, when the mobile phase in the column chromatography is petroleum ether and ethyl acetate, the volume ratio of petroleum ether to ethyl acetate is 100:1-1:1.

[0020] Further, the organic solvent is acetonitrile, and the volume ratio of the acetonitrile solvent to the substance amount of hexamethylditin is 1:0.3-2:0.3.

[0021] Further, the concentration is performed by normal pressure distillation or reduced pressure distillation.

[0022] Further, the visible light is blue light, and the reaction time is 11-12 hours.

[0023] The beneficial effects of the present application are as follows:

[0024] 1. The raw material adopted by the present application is aryl iodine or aryl bromine without pre-activation, which is widely available, cheap and easy to obtain, and has low production cost and is convenient to store.

[0025] 2. The reaction method of the present application has good tolerance and universality to functional groups, and the substituent group on the aryl tin can be methanesulfonyl, acetoxy, cyano, methoxy, alkynyl, hydroxymethyl.

[0026] 3. The reaction condition of the present application is relatively mild, and does not need transition metal catalysis and high temperature heating; the dosage of hexamethylditinane is low, the reaction condition is safe, and it is suitable for large-scale production and development.

[0027] 4. The yield of aryl trimethyltinane prepared by the tin reaction method of the present application is high, and the yield can reach up to 95%. Embodiment

[0028] The equation of the tin reaction method of the present application is:

[0029] +(SnMe3)2

[0030] X=Br, I.

[0031] 2,4,5,6-tetra(9-carbazolyl)-m-benzene dicarbonitrile is used as a photocatalyst, aryl iodine or aryl bromine, N,N-diisopropyl ethylamine, hexamethylditinane are jointly used in a solvent to form aryl trimethyltinane.

[0032] The technical scheme of the present application will be further described below in combination with specific embodiments.

[0033] In the following examples, the organic solvent is acetonitrile.

[0034] In the following examples, the purchase sources of the medicines are as follows:

[0035] .

[0036] The structural formula of hexamethylditin is: wherein Me is methyl.

[0037] The instrument model of nuclear magnetic resonance is AVANCE III 4000 MHz, and the manufacturer is Bruker Company, Switzerland.

[0038] The concentration can adopt methods such as atmospheric distillation or reduced pressure distillation, and the concentration in the following examples is removal of solvent by a rotary evaporator under vacuum, the model and manufacturer of the rotary evaporator are SHB-III circulating water type multi-purpose vacuum pump, R-1001N of Zhengzhou Great Wall Science and Technology Co., Ltd.

[0039] Yield: the yield of the tin reaction method for obtaining the product, aryltrimethylstannane, is calculated by dividing the amount of substance of aryltrimethylstannane by the amount of substance of aryl bromide or aryl iodide. Example

[0040] The tin reaction method for synthesizing (4-(trimethylstannyl)phenyl)methanol prepared in this example includes the following steps:

[0041] Under a nitrogen atmosphere, 0.002 mmol of 4-CzIPN was added to a dry 10 mL long-tube type reaction bottle, followed by sequentially adding 1.0 mL of acetonitrile, 0.2 mmol of 4-iodobenzyl alcohol, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA, and the reaction system was stirred at room temperature under irradiation of a 24W blue LED lamp for 12 hours. After the reaction was completed, the product was concentrated and purified by column chromatography with petroleum ether: ethyl acetate = 5:1 (volume ratio) as the eluent (total amount of mobile phase 200 mL) to obtain (4-(trimethylstannyl)phenyl)methanol.

[0042] 4-iodobenzyl alcohol is a reactant, and its structural formula is: , and the structural formula of (4-(trimethylstannyl)phenyl)methanol is: .

[0043] The product obtained in this example is a colorless liquid, and the yield is 94%; the nuclear magnetic resonance data is as follows:

[0044] 1 H NMR (400 MHz, CDCl3) δ 7.50 (d, J = 7.9 Hz, 2H), 7.34 (d, J = 7.8Hz, 2H), 4.66 (s, 2H), 0.29 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 141.6, 140.8,136.0, 126.7, 65.4, -9.6. Example

[0045] The tin reaction method for synthesizing the (4-(methylsulfonyl)phenyl)trimethylstannane prepared in this embodiment includes the following steps:

[0046] In a dry 10 mL long-tube type reaction bottle, 0.002 mmol of 4-CzIPN was added under nitrogen atmosphere, followed by 1.0 mL of acetonitrile, 0.2 mmol of 1-iodo-4-methylsulfonylbenzene, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA, and the reaction system was stirred at room temperature under irradiation of a 24 W blue LED lamp for 12 hours. After the reaction was completed, it was concentrated and purified by column chromatography with petroleum ether: ethyl acetate = 20:1 (volume ratio) as the eluent (total amount of mobile phase 250 mL) to obtain (4-(methylsulfonyl)phenyl)trimethylstannane.

[0047] 1-iodo-4-methylsulfonylbenzene is a reactant, and its structural formula is: The structural formula of (4-(methylsulfonyl)phenyl)trimethylstannane is: .

[0048] The product obtained in this embodiment is a colorless liquid, and the yield is 95%; its nuclear magnetic resonance data are as follows:

[0049] 1 H NMR (400 MHz, CDCl3) δ 7.87 (d, J = 8.2 Hz, 2H), 7.70 (d, J = 8.1Hz, 2H), 3.04 (s, 3H), 0.35 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 151.3, 140.3,136.6, 126.0, 44.5, -9.5. HRMS (ESI) m / z calcd for C 10 H 17 O2SSn + (M+H) + 320.9966,found 320.9963. Example

[0050] The tin reaction method for synthesizing the (4-(methylsulfonyl)phenyl)trimethylstannane prepared in this embodiment includes the following steps:

[0051] Into a 10 mL dry tube, 0.002 mmol of 4-CzIPN was added, followed by 1.0 mL of acetonitrile, 0.2 mmol of 4-iodoacetylphenol, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA. The reaction system was stirred at room temperature for 12 hours under the irradiation of a 24 W blue LED lamp. After the reaction was completed, the reaction system was concentrated and purified by column chromatography with petroleum ether: ethyl acetate = 30: 1 (volume ratio) as the eluent (total amount of mobile phase 250 mL) to obtain 4-(trimethylstannyl)phenyl acetate.

[0052] 4-iodoacetylphenol is a reactant, and its structural formula is: The structural formula of 4-(trimethylstannyl)phenyl acetate is: .

[0053] The product obtained in this example is a colorless liquid, and the yield is 83%; the nuclear magnetic resonance data is as follows:

[0054] 1 H NMR (400 MHz, CDCl3) δ 7.50 (d, J = 7.3 Hz, 2H), 7.06 (d, J = 7.3Hz, 2H), 2.30 (s, 3H), 0.28 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 169.5, 151.0,139.6, 136.8, 121.2, 21.1, -9.5. HRMS (ESI) m / z calcd for C 11 H 17 O2Sn + (M+H) + 301.02450, found 301.02448. Example

[0055] The tin reaction method for synthesizing ((4-(trimethylstannyl)phenyl)ethynyl)trimethylsilane prepared in this example includes the following steps:

[0056] Into a dry 10 mL test tube, 0.002 mmol of 4-CzIPN was added, followed by 1.0 mL of acetonitrile, 0.2 mmol of (4-iodophenylacetylene)trimethylsilane, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA. The reaction mixture was stirred at room temperature under irradiation of a 24 W blue LED lamp for 12 h. After the reaction was completed, the mixture was concentrated and purified by column chromatography with petroleum ether as the eluent (total amount of mobile phase 200 mL) to obtain ((4-(trimethyltin)phenyl)ethynyl)trimethylsilane.

[0057] (4-iodophenylacetylene)trimethylsilane is a reactant, and its structural formula is: , and the structural formula of ((4-(trimethyltin)phenyl)ethynyl)trimethylsilane is: .

[0058] The product obtained in this example is a colorless liquid, and the yield is 94%. The nuclear magnetic resonance data are as follows:

[0059] 1 H NMR (400 MHz, CDCl3) δ 7.43-7.38 (m, 4H), 0.28 (s, 9H), 0.24 (s,9H). 13 C NMR (100 MHz, CDCl3) δ 135.5, 132.0, 131.1, 128.2, 105.3, 94.2, 0.0, -9.6. HRMS (ESI) m / z calcd for C 14 H 22 SiSn + (M+H) + 339.0586, found 339.0358. Example

[0060] The pyrrolidin-1-yl(4-(trimethyltin)phenyl)methanone prepared in this example, and the tin reaction method for synthesizing the same comprises the following steps:

[0061] Into a 10 mL dry tube, 0.002 mmol of 4-CzIPN was added, followed by 1.0 mL of acetonitrile, 0.2 mmol of 4-(pyrrolinylcarbonyl) bromobenzene, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA. The reaction system was stirred at room temperature under irradiation of a 24 W blue LED lamp for 12 hours. After the reaction was completed, the reaction system was concentrated and purified by column chromatography with petroleum ether: ethyl acetate = 3:1 (volume ratio) as eluent (total amount of mobile phase 200 mL) to obtain pyrrolidin-1-yl(4-(trimethylstannyl)phenyl)methanone.

[0062] 4-(pyrrolinylcarbonyl) bromobenzene is a reactant, and its structural formula is: The structural formula of pyrrolidin-1-yl(4-(trimethylstannyl)phenyl)methanone is: .

[0063] The product obtained in this example is a colorless liquid, and the yield is 95%; its NMR data are as follows:

[0064] 1 H NMR (400 MHz, CDCl3) δ 7.52 (d, J = 7.6 Hz, 2H), 7.46 (d, J = 6.3Hz, 2H), 3.64 (t, J = 6.9 Hz, 2H), 3.43 (t,J = 6.5 Hz, 2H), 1.95 (t, J = 6.8Hz, 2H), 1.86 (t, J = 6.6 Hz, 2H), 0.30 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ169.7, 144.8, 136.9, 135.5, 126.3, 49.5, 46.1, 26.3, 24.4, -9.6。 Example

[0065] The tin reaction method for synthesizing (3-methoxyphenyl)trimethylstannane prepared in this example includes the following steps:

[0066] Into a dry 10 mL test tube, 0.002 mmol of 4-CzIPN was added, followed by 1.0 mL of acetonitrile, 0.2 mmol of 3-bromoanisole, 131 mg (i.e. 0.4 mmol) of hexamethylditin and 0.2 mmol of DIPEA. The reaction system was stirred at room temperature for 12 hours under irradiation of a 24 W blue LED lamp. After the reaction was completed, the product was purified by column chromatography with petroleum ether: ethyl acetate = 100:1 (volume ratio) as the eluent (total amount of mobile phase 350 mL) to obtain (3-methoxyphenyl)trimethylstannane.

[0067] 3-bromoanisole is a reactant, and its structural formula is: The structural formula of (3-methoxyphenyl)trimethylstannane is: .

[0068] The product obtained in this example is colorless, and the yield is 92%; the nuclear magnetic resonance data is as follows:

[0069] 1 H NMR (400 MHz, CDCl3) δ 7.16 (dd, J = 8.3, 7.0 Hz, 1H), 6.99-6.88(m, 2H), 6.73 (dd, J = 8.4, 2.0 Hz, 1H), 3.69 (s, 3H), 0.16 (s, 9H). 13 C NMR(100 MHz, CDCl3) δ 159.1, 143.7, 129.0, 128.0, 121.4, 113.4, 55.1, -9.6。 Example

[0070] The tin reaction method for synthesizing the prepared benz[d][1,3]dioxol-5-yltrimethylstannane includes the following steps:

[0071] Into a dry 10 mL test tube, 0.002 mmol of 4-CzIPN was added, followed by 1.0 mL of acetonitrile, 0.2 mmol of 3-bromoanisole, 131 mg (i.e. 0.4 mmol) of hexamethylditin and 0.2 mmol of DIPEA. The reaction system was stirred at room temperature for 12 hours under irradiation of a 24 W blue LED lamp. After the reaction was completed, the product was purified by column chromatography with petroleum ether: ethyl acetate = 100:1 (volume ratio) as the eluent (total amount of mobile phase 350 mL) to obtain (3-methoxyphenyl)trimethylstannane.

[0072] 1-iodo-3,4-methylenedioxybenzene is a reactant, and its structural formula is: The structural formula of benz[d][l,3]dioxol-5-yltrimethylstannane is as follows: .

[0073] The product obtained in the example is a colorless liquid, and the yield is 87%; the nuclear magnetic data thereof are as follows:

[0074] 1 H NMR (400 MHz, CDCl3) δ 6.99-6.89 (m, 2H), 6.86 (d, J = 7.4 Hz, 1H),5.92 (s, 2H), 0.27 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ 147.8, 147.5, 134.4,129.0, 115.0, 108.9, 100.3, -9.4. Example

[0075] The tin reaction method for synthesizing 5-(trimethyltin)nicotinonitrile prepared in the example includes the following steps:

[0076] In a nitrogen atmosphere, 0.002 mmol of 4-CzIPN was added to a dry 10 mL long-tube type reaction bottle, and then 1.0 mL of acetonitrile, 0.2 mmol of 5-iodine potassium nitrile, 131 mg (i.e. 0.4 mmol) of hexamethylditin and 0.2 mmol of DIPEA were sequentially added, and the reaction system was stirred at room temperature under irradiation of a 24W blue LED lamp for 12 hours. After the reaction was completed, it was concentrated, and column chromatography purification was carried out with petroleum ether: ethyl acetate = 1:1 (volume ratio) as the eluent (total amount of mobile phase 250 mL) to obtain 5-(trimethyltin)nicotinonitrile.

[0077] 5-iodine potassium nitrile is a reactant, and the structural formula thereof is as follows: The structural formula of 5-(trimethyltin)nicotinonitrile is as follows: .

[0078] The product obtained in the example is a colorless liquid, and the yield is 92%; the nuclear magnetic data thereof are as follows:

[0079] 1 H NMR (400 MHz, CDCl3) δ 8.85-8.76 (m, 2H), 8.03 (s, 1H), 0.40 (s,9H). 13 C NMR (100 MHz, CDCl3) δ 158.4, 151.7, 146.3, 138.2, 117.1, 110.3, -9.4. Example

[0080] The (naphthalen-2-yl)trimethylstannane prepared in this example, the stannation reaction method for synthesizing the same includes the following steps:

[0081] Under a nitrogen atmosphere, 0.002 mmol of 4-CzIPN was added to a dry 10 mL long-tube type reaction bottle, followed by sequentially adding 1.0 mL of acetonitrile, 0.2 mmol of 2-iodonaphthalene, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA, and the reaction system was stirred at room temperature for 12 hours under irradiation of a 24W blue LED lamp. After the reaction was completed, it was concentrated, and column chromatography purification was performed with petroleum ether as the eluent (total amount of mobile phase 200 mL) to obtain (naphthalen-2-yl)trimethylstannane.

[0082] 2-iodonaphthalene is a reactant, and its structural formula is: The structural formula of (naphthalen-2-yl)trimethylstannane is: .

[0083] The product obtained in this example is a colorless liquid, and the yield is 87%; its nuclear magnetic resonance data are as follows:

[0084] 1 H NMR (400 MHz, CDCl3) δ 7.96 (s, 1H), 7.83-7.78 (m, 3H), 7.58 (d, J= 8.0 Hz, 1H), 7.48-7.43 (m, 2H), 0.35 (s, 9H). 13 C NMR (100 MHz, CDCl3) δ139.8, 135.9, 133.3, 133.2, 132.3, 127.8, 127.5, 127.0, 125.9, 125.8, -9.5。 Example

[0085] The 2-(trimethylstannyl)anthracene-9,10-dione prepared in this example, the stannation reaction method for synthesizing the same includes the following steps:

[0086] Under a nitrogen atmosphere, 0.002 mmol of 4-CzIPN was added to a dry 10 mL long-tube type reaction bottle, followed by sequentially adding 1.0 mL of acetonitrile, 0.2 mmol of 2-iodonaphthalene, 131 mg (i.e. 0.4 mmol) of hexamethyldistannane and 0.2 mmol of DIPEA, and the reaction system was stirred at room temperature for 12 hours under irradiation of a 24W blue LED lamp. After the reaction was completed, it was concentrated, and column chromatography purification was performed with petroleum ether: ethyl acetate = 1:1 (by volume) as the eluent (total amount of mobile phase 250 mL) to obtain 2-(trimethylstannyl)anthracene-9,10-dione.

[0087] 2-iodoanthracene-9,10-dione is a reactant, and its structural formula is: , and the structural formula of 2-(trimethyltin)anthracene-9,10-dione is: .

[0088] The product obtained in this example is a colorless liquid, and the yield is 85%; the nuclear magnetic data thereof are as follows:

[0089] 1 H NMR (400 MHz, CDCl3) δ 8.44 (s, 1H), 8.34-8.27 (m, 2H), 8.21 (d, J= 7.5 Hz, 1H), 7.95 (d, J = 7.4 Hz, 1H), 7.85-7.75 (m, 2H), 0.40 (s, 9H). 13 CNMR (100 MHz, CDCl3) δ 183.9, 183.6, 152.4, 141.7, 134.3, 134.1, 134.0,133.5, 133.4, 133.1, 131.6, 127.14, 127.07, 125.6, -9.3. HRMS (ESI) m / z calcdfor C 17 H 17 O2Sn + (M+H) + 373.0245, found 373.0244.

[0090] In the technical solution of the present application, by adjusting the addition amount of 4-CzIPN (0.01 eq~0.03 eq), the same technical effect as the above example can be achieved.

[0091] In the technical solution of the present application, by adjusting the order of adding aryl bromide or aryl iodide, DIPEA, and hexamethyl ditin into the long-tube type reaction bottle, the same technical effect as the above example can be achieved.

[0092] The above has made an exemplary description of the present application, and it should be explained that, without departing from the core of the present application, any simple modification, modification or other equivalent replacement which can not cost creative labor of those skilled in the art falls within the protection scope of the present application.

Claims

1. A method for preparing an aryltrimethylstannane compound, characterized in that, Aryl halides, 2,4,5,6-Tetra(9-carbazolyl)-isophthalonitrile, N,N-diisopropylethylamine, and hexamethyldistin are mixed in an organic solvent and reacted under visible light catalysis. The reaction formula is as follows: +(SnMe3) 2 , =Ar， After the reaction was completed, the mixture was concentrated to remove the solvent; then column chromatography was performed to obtain a pure aryltrimethyltin compound. The aryl halogenated compounds are 4-iodobenzyl alcohol, 1-iodo-4-methylsulfonylbenzene, 4-iodoacetylphenol, (4-iodophenylacetylene)trimethylsilane, 4-(pyrrololinylcarbonyl)bromobenzene, 3-bromoanisole, 1-iodo-3,4-methylenedioxybenzene, 5-potassium iodide nitrile, 2-iodonaphthalene, or 2-iodoanthracene-9,10-dione; The aryltrimethyl compound is (4-(trimethyltin)phenyl)methanol or (4-(methanesulfonyl)phenyl)trimethylstanane or 4-(trimethyltin)phenylacetate or ((4-(trimethyltin)phenyl)ethynyl)trimethylsilane or pyrrolidone-1-yl(4-(trimethyltin)phenyl)methyl ketone or (3-methoxyphenyl)trimethylstanane or benzo[d][1,3]dioxolane-5-yltrimethylstanane or 5-(trimethyltin)nicotinonitrile or (naphth-2-yl)trimethylstanane or 2-(trimethyltin)anthracene-9,10-dione; The molar ratio of the aryl halide, 2,4,5,6-tetrakis(9-carbazolyl)-isophthalonitrile, N,N-diisopropylethylamine, and hexamethyldistin is 1:(0.01~0.03):1(1~2). The mobile phase in the column chromatography is petroleum ether and / or ethyl acetate. When the mobile phase in the column chromatography is petroleum ether and ethyl acetate, the volume ratio of petroleum ether to ethyl acetate is 100:1 to 1:

1. The organic solvent is acetonitrile, and the volume ratio of the acetonitrile solvent to the molar ratio of hexamethyldistin is 1:0.3-2:0.

3. The concentration is achieved by atmospheric distillation or vacuum distillation; The visible light is blue light, and the reaction time is 11-12 hours.

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