CN110105337B - Quinoline triarylamine and preparation method thereof - Google Patents
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Abstract
The invention relates to a method for preparing quinoline triarylamine and a preparation method thereof. Taking substituted 8-aminoquinoline compounds (I) and carbazole compounds (II) as substrates, adding a nickel catalyst with a mole fraction of 1-30% (relative to primary amine compounds I, the same below), 2-5 molar equivalents of alkali and 2mL of organic solvent as solvents, stirring the reaction mixture at 25-160 ℃ for 1-48 hours under the atmosphere of nitrogen, adding saturated ammonium chloride solution for quenching after the reaction is completed, extracting with a polar organic solvent, adding anhydrous sodium sulfate or anhydrous magnesium sulfate for drying, concentrating by a rotary evaporator, and separating by column chromatography to obtain the target product triarylamine compound (III). The method has the advantages of low cost of catalyst, high yield, simple and convenient operation, no generation of harmful by-products and the like, and has certain feasibility for realizing industrial production. The synthesized quinoline triarylamine compound can be converted into various functional molecules through various series reactions or cross-coupling reactions, and has potential application value in the fields of biomedicine and materials.
Description
[ technical field ] A method for producing a semiconductor device
The invention belongs to the field of catalytic organic synthesis, and particularly relates to a novel method for preparing a quinolyl triarylamine compound by using a substituted 8-aminoquinoline compound and a substituted carbazole compound under the condition of taking transition metal nickel as a catalyst. The method uses 8-aminoquinoline compounds containing different substituents and carbazole compounds containing different substituents as main raw materials, transition metal nickel as a catalyst, a polar organic solvent as a solvent, inorganic salt as alkali, and the like in the presence of N 2 Reacting for 1-48h at 25-160 ℃ in the atmosphere, and preparing the quinolyl triarylamine compound with high yield.
[ background of the invention ]
Triarylamine compounds are important compounds, and particularly triarylamine compounds with large steric hindrance and large conjugated systems are widely applied to the fields of photoelectric materials, medical intermediates, organic dyes and the like. In recent years, organic functional materials have played an increasingly important role in daily production life. With the rapid development of organic light emitting diodes, especially the display technology has the advantages of self-luminescence, wide viewing angle, almost infinite contrast, lower power consumption, extremely high reaction speed, etc., and the material of the hole transport layer in the OLED is mainly triarylamine. This also makes the efficient synthesis of triarylamine a research direction for organic synthesis researchers. Triarylamine compounds have a very important role, but their synthesis is not easy. The traditional method for synthesizing triarylamine is mainly based on diarylamine, and further arylation is realized by Buchwald-Hartwig coupling reaction or Ullmann condensation reaction. In conventional synthesis methods, the synthesis of triarylamines is achieved. In recent years, there have been some advances in constructing triarylamines by starting directly from primary amines. In 2009, yasuhirouzumi et al reported that palladium is supported on amphiphilic PS-PEG resin to realize a catalytic triarylamine reaction; in 2015, mikhail s. Nechaev et al reported a method of constructing triarylamines via an expansile N-heterocyclic carbene palladium complex. In 2002, raghunathv. Chaudhari et al reported copper-catalyzed syntheses of triarylamines from primary amines. However, in the case of the aromatic hydrocarbon having large steric hindrance, the reaction efficiency is low because the large steric hindrance is not easily caused by the oxidative addition of the metal catalyst. Based on the above reports, we designed a cheap transition metal nickel catalytic system. 8-aminoquinoline with coordination ability is selected as a reaction substrate, and forms an efficient complex with catalyst nickel, so that the activation energy of diarylamine after coordination with metal is reduced, and the conversion efficiency of diarylamine to triarylamine is promoted, thereby realizing the synthesis of triarylamine compounds with large steric hindrance by a one-pot method starting from primary amine. The method realizes that the cheap metallic nickel catalyzes primary amine and the bromocarbazole derivative with large steric hindrance to form triarylamine by a one-pot method, and has certain industrial application prospect.
[ summary of the invention ]
The invention aims to provide a novel method for preparing a quinolyl triarylamine compound (III). The preparation method is to use 8-amino containing different substituentsQuinoline compounds I and carbazole compounds II with different substituents as main raw materials, transition metal nickel as a catalyst, a polar organic solvent as a solvent, inorganic salt as alkali and N 2 Reacting for 1-48h at 25-160 ℃ in the atmosphere, and preparing the quinolyl triarylamine compound with high yield. The method has the advantages of high yield, simple and convenient operation and certain feasibility for realizing industrial production.
Characterized in that the substrate primary amine I is 8-aminoquinoline (R) 1 = hydrogen), 8-amino-5-phenylthioquinoline (R) 1 = 5-thiophenyl), 8-amino-6-methoxyquinoline (R) 1 = 6-methoxy), 8-amino-5-phenylquinoline (R) 1 = 5-phenyl), 8-amino-2-methylquinoline (R) 1 = 2-methyl), 8-amino-4-phenylquinoline (R) 1 = 4-phenyl), 8-amino-5, 7-dichloroquinoline (R) 1 One of 5, 7-dichloro);
the substrate carbazole II is 9- (4-bromophenyl) carbazole (R) 2 = Hydrogen), 9- (4-bromophenyl) -3, 6-di-tert-butylcarbazole (R) 2 =3, 6-di-tert-butyl), 9- (4-bromophenyl) -3, 6-dibromocarbazole (R) 2 =3, 6-dibromo), 9- (4-bromophenyl) -2, 7-dibromocarbazole (R) 2 =2, 7-dibromo), 9- (4-bromophenyl) -1, 8-diphenyl sulfide carbazole (R) 2 =1, 8-diphenylthio), 9- (4-bromophenyl) -1, 8-diphenylcarbazole (R) 2 =1, 8-diphenyl), 9- (4-bromophenyl) -1-phenylcarbazole (R) 2 = 1-phenyl), 9- (4-bromophenyl) -1-phenylthioethercarbazole (R) 2 = 1-phenylthio), one of 9- (4-bromophenyl) -1.2.3.4-tetrahydrocarbazole, the amount is 2.0 equivalents to 5.0 equivalents;
the substrate III is quinolyl triarylamine, and the nitrogen atom of the quinoline amino is connected with the para-position of the benzene ring of two molecules of carbazole derivatives.
In order to achieve the above purpose, the invention provides the following technical scheme:
the synthetic route is shown in the attached drawings of the specification, and is characterized in that: taking a substituted 8-aminoquinoline compound I and a bromocarbazole compound II as substrates, adding a nickel catalyst with a mole fraction of 1-30% (relative to a primary amine compound I, the same below), 1-5 molar equivalents of alkali and a common organic solvent as solvents, stirring the reaction mixture at 25-160 ℃ for 1-48 hours under the atmosphere of nitrogen, adding a saturated ammonium chloride solution for quenching after the reaction is completed, extracting with a polar organic solvent, adding anhydrous sodium sulfate or anhydrous magnesium sulfate for drying, concentrating by a rotary evaporator, and separating by column chromatography to obtain a target product triarylamine compound III.
In the preparation method, the reaction solvent is one of tetrahydrofuran, dimethyl sulfoxide, N-methylpyrrolidone, N, N-dimethylformamide, N, N-dimethylacetamide, toluene, p-xylene and acetonitrile.
In the above preparation method, the nickel catalyst used is nickel fluoride, nickel chloride, nickel bromide, nickel acetate, nickel sulfate, nickel acetate, nickel trifluoroacetate, nickel trifluoromethanesulfonate, nickel acetylacetonate, (1, 1' -bis (diphenylphosphino) ferrocene) nickel dichloride, bis- (1, 5-cyclooctadiene) nickel (Ni (COD) 2 ) The amount is 1 to 30 mol%.
In the preparation method, the alkali is one of potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, sodium tert-butoxide and potassium tert-butoxide, and the dosage is 2-5 equivalents.
In the preparation method, the reaction condition is that the reaction is carried out for 1 to 48 hours at a temperature of between 25 and 160 ℃.
The method provided by the invention develops a high-efficiency new way for preparing the quinolyl triarylamine compound. The method has the advantages of using cheap metal catalyst, high yield, starting from primary amine to synthesize by a one-pot method, and simple and convenient operation.
[ description of the drawings ]
The attached figure shows a synthetic route diagram of the quinolyl triarylamine compound (III).
[ detailed description ] embodiments
The invention provides a method for preparing a quinolyl triarylamine compound by using a substituted 8-amino quinoline compound and a substituted carbazole compound under the condition of taking transition metal nickel as a catalyst. The method comprises the steps ofThe substituted 8-aminoquinoline compound I and the carbazole compound II with different substituents are used as main raw materials, transition metal nickel is used as a catalyst, a polar organic solvent is used as a solvent, inorganic salt is used as alkali, and the reaction is carried out in the presence of N 2 Reacting for 1-48h at 25-160 ℃ in the atmosphere, and preparing the quinolyl triarylamine compound with high yield.
The invention is further illustrated below with reference to specific preparation examples:
preparation example 1
1 piece of 8-amino-5-thiophenylquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel chloride (0.06 mmol) and potassium carbonate (1.2 mmol) were added to a 10mL reaction tube with a magnetic stirrer, and then the reaction tube was evacuated and filled with nitrogen 3 times, followed by addition of tetrahydrofuran (2 mL) under a nitrogen atmosphere and reaction at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -5- (phenylthio) -8-aminoquinoline with the yield of 97%.
Preparation example 2
A10 mL reaction tube was charged with 1 particle of a magnetic stirrer, 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel bromide (0.06 mmol), and potassium carbonate (1.2 mmol), evacuated and filled with nitrogen gas 3 times, and tetrahydrofuran (2 mL) was added under nitrogen atmosphere to react at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -8-aminoquinoline with the yield of 95%.
Preparation example 3
1 piece of 8-amino-6-methoxyquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel fluoride (0.03 mmol) and potassium carbonate (0.9 mmol) were added to a 10mL reaction tube with a magnetic stirrer, and the reaction tube was evacuated and filled with nitrogen 3 times, and tetrahydrofuran (2 mL) was added under a nitrogen atmosphere to react at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -6- (methoxyl) -8-aminoquinoline with the yield of 93%.
Preparation example 4
1 piece of 8-amino-5-phenylquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel fluoride (0.03 mmol), and potassium carbonate (0.9 mmol) were added to a 10mL reaction tube with a magnetic stirrer, and the reaction tube was evacuated and filled with nitrogen 3 times, and tetrahydrofuran (2 mL) was added under a nitrogen atmosphere, followed by reaction at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -5- (phenyl) -8-aminoquinoline with the yield of 91%.
Preparation example 5
1 piece of 8-amino-2-methylquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel acetylacetonate (0.03 mmol) and potassium carbonate (0.9 mmol) were magnetically stirred in a 10mL reaction tube, and then evacuated and filled with nitrogen 3 times, followed by addition of tetrahydrofuran (2 mL) under a nitrogen atmosphere and reaction at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -2- (methyl) -8-aminoquinoline with the yield of 90%.
Preparation example 6
1 piece of 5-bromo-8-aminoquinoline, 9- (4-bromophenyl) carbazole (0.6 mmol), nickel sulfate (0.03 mmol) and potassium carbonate (0.9 mmol) were added to a 10mL reaction tube with a magnetic stirrer, and then evacuated and filled with nitrogen gas 3 times, and dimethyl sulfoxide (2 mL) was added thereto under a nitrogen atmosphere to react at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -5-bromo-8-aminoquinoline with the yield of 89%.
Preparation example 7
A10 mL reaction tube was charged with 1 particle of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel chloride (0.06 mmol), and potassium tert-butoxide (1.2 mmol) with a magnetic stirrer, and the reaction tube was evacuated and filled with nitrogen 3 times, and tetrahydrofuran (2 mL) was added under a nitrogen atmosphere, followed by reaction at 160 ℃ for 1 hour. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl)) -8-aminoquinoline with the yield of 95%. The excitation wavelength of the obtained compound is 260-400nm, the emission wavelength is 540nm, and the Stokes shift is large.
Preparation example 8
A10 mL reaction tube was charged with 1 magnetic stirrer, 8-aminoquinoline, 9- (4-bromophenyl) carbazole (0.6 mmol), nickel sulfate (0.03 mmol), and potassium carbonate (0.6 mmol), evacuated, filled with nitrogen gas 3 times, charged with tetrahydrofuran (2 mL) under nitrogen atmosphere, and reacted at 25 ℃ for 48 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl)) -8-aminoquinoline with the yield of 70%.
Preparation example 10
1 piece of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) carbazole (0.6 mmol), nickel trifluoroacetate (0.003 mmol) and potassium carbonate (1.5 mmol) were magnetically stirred in a 10mL reaction tube, and the reaction tube was evacuated and filled with nitrogen gas for 3 times, and N-methylpyrrolidone (2 mL) was added under a nitrogen atmosphere, followed by reaction at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) -phenyl) -8-aminoquinoline with the yield of 75%.
Preparation example 11
A10 mL reaction tube was charged with 1 particle of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) -3, 6-di-t-butylcarbazole (0.6 mmol), nickel trifluoroacetate (0.09 mmol) and potassium carbonate (0.9 mmol) under a magnetic stirrer, evacuated and filled with nitrogen gas 3 times, and then charged with tetrahydrofuran (2 mL) under a nitrogen atmosphere, and reacted at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-3, 6-di-tert-butyl carbazole-9-yl) -phenyl) -8-aminoquinoline with the yield of 87%.
Preparation example 12
1 particle of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) -3, 6-di-tert-butylcarbazole (0.6 mmol), nickel trifluoromethanesulfonate (0.03 mmol) and potassium carbonate (0.9 mmol) were placed in a 10mL reaction tube, and then evacuated and filled with nitrogen gas 3 times, N-dimethylacetamide (2 mL) was added under nitrogen atmosphere, and the mixture was reacted at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-3, 6-di-tert-butyl carbazole-9-yl) -phenyl) -8-aminoquinoline with the yield of 88%.
Preparation example 13
A10 mL reaction tube was charged with 1 particle of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) -3, 6-dibromocarbazole (0.6 mmol), nickel acetylacetonate (0.03 mmol) and sodium carbonate (0.9 mmol) under magnetic stirring, evacuated and filled with nitrogen gas for 3 times, and then toluene (2 mL) was added under nitrogen atmosphere to react at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-3, 6-dibromocarbazole-9-yl) -phenyl) -8-aminoquinoline with the yield of 89%.
Preparation example 14
A10 mL reaction tube was charged with 1 particle of 8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) -1.2.3.4-tetrahydrocarbazole (0.6 mmol), (1, 1' -bis (diphenylphosphino) ferrocene) dichloronickel (0.03 mmol), and sodium bicarbonate (0.9 mmol) under magnetic stirring, evacuated and filled with nitrogen gas for 3 times, N-dimethylacetamide (2 mL) was added under nitrogen atmosphere, and reacted at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-1.2.3.4-tetrahydrocarbazole-9-yl) -phenyl) -8-aminoquinoline with the yield of 90%.
Preparation example 15
In 10mLMagnetic stirrers 1, 4-phenyl-5-bromo-8-aminoquinoline, 9- (4-bromophenyl) carbazole (0.6 mmol), bis- (1, 5-cyclooctadiene) nickel (Ni (COD) were added to the reaction tube 2 ) (0.03 mmol) and potassium hydrogencarbonate (0.9 mmol) were added to the mixture in a vacuum atmosphere, followed by filling nitrogen gas in the mixture 3 times, adding p-xylene (2 mL) under nitrogen atmosphere, and reacting the mixture at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -4-phenyl-5-bromo-8-aminoquinoline with the yield of 85%.
Preparation example 16
1 piece of 4-phenyl-5-bromo-8-aminoquinoline, 9- (4-bromophenyl) carbazole (0.6 mmol), nickel sulfate (0.03 mmol), and cesium carbonate (0.9 mmol) were added to a 10mL reaction tube with a magnetic stirrer, and the mixture was evacuated and filled with nitrogen 3 times, and acetonitrile (2 mL) was added under a nitrogen atmosphere, followed by reaction at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-carbazole-9-yl) phenyl) -4-phenyl-8-aminoquinoline with the yield of 86%.
Preparation example 17
A10 mL reaction tube was charged with 1 magnetic stirrer, 8-aminoquinoline, 9- (4-bromophenyl) carbazole (0.6 mmol), nickel sulfate (0.03 mmol), and sodium tert-butoxide (0.9 mmol), and the reaction was carried out under vacuum with nitrogen gas for 3 times, in which tetrahydrofuran (2 mL) was charged under nitrogen gas atmosphere, and the reaction was carried out at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-3-bromocarbazole-9-yl) phenyl) -4-phenyl-8-aminoquinoline with the yield of 86%.
Preparation example 18
A10 mL reaction tube was charged with 1 particle of 5-chloro-8-aminoquinoline (0.3 mmol), 9- (4-bromophenyl) -1.2.3.4-tetrahydrocarbazole (0.6 mmol), nickel trifluoroacetate (0.03 mmol), and potassium tert-butoxide (0.9 mmol) under magnetic stirring, and the reaction tube was evacuated and filled with nitrogen gas for 3 times, and tetrahydrofuran (2 mL) was added under nitrogen atmosphere to react at 100 ℃ for 24 hours. After the reaction is finished, adding saturated ammonium chloride aqueous solution for quenching, extracting by ethyl acetate, drying, concentrating, and separating by column chromatography to obtain the N, N-bis (4- (9H-1.2.3.4-tetrahydrocarbazole-9-yl) -phenyl) -5-chloro-8-aminoquinoline with the yield of 90%.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the present patent should be subject to the appended claims.
Claims (5)
1. A preparation method of quinolyl triarylamine comprises the following steps of preparing raw materials and a target product triarylamine compound III, wherein the structural formula of the triarylamine compound III is as follows:
the method is characterized in that a substrate primary amine compound I is one of 8-aminoquinoline, 8-amino-5-phenylthioquinoline, 8-amino-6-methoxyquinoline, 8-amino-5-phenylquinoline, 8-amino-2-methylquinoline, 8-amino-4-phenylquinoline and 8-amino-5, 7-dichloroquinoline;
the substrate carbazole II is one of 9- (4-bromophenyl) carbazole, 9- (4-bromophenyl) -3, 6-di-tert-butyl carbazole, 9- (4-bromophenyl) -3, 6-dibromocarbazole, 9- (4-bromophenyl) -2, 7-dibromocarbazole, 9- (4-bromophenyl) -1, 8-diphenyl sulfide carbazole, 9- (4-bromophenyl) -1, 8-diphenyl carbazole, 9- (4-bromophenyl) -1-phenyl carbazole, 9- (4-bromophenyl) -1-diphenyl sulfide carbazole, 9- (4-bromophenyl) -1.2.3.4-tetrahydrocarbazole, and the amount of the carbazole II is 2.0 to 5.0 equivalents relative to the amount of the primary amine compound I;
the target product triarylamine compound III is quinolyl triarylamine, and the nitrogen atom of the quinoline amino is connected with the para-position of the benzene ring of two molecules of carbazole derivatives;
the synthesis method is characterized in that substituted 8-aminoquinoline compounds I and bromocarbazole compounds II are used as substrates, a nickel catalyst with the mole fraction of 1-30% and 1-5 molar equivalent of alkali are added, an organic solvent is used as a solvent, a reaction mixture is stirred and reacted for 1-48 hours at the temperature of 25-160 ℃ under the atmosphere of nitrogen, a saturated ammonium chloride solution is added for quenching after the reaction is completed, a polar organic solvent is used for extraction, anhydrous sodium sulfate or anhydrous magnesium sulfate is added for drying, and a target product triarylamine compound III is obtained by concentration of a rotary evaporator and column chromatographic separation.
2. The method according to claim 1, wherein the organic solvent is one of tetrahydrofuran, dimethylsulfoxide, N-methylpyrrolidone, N-dimethylformamide, N-dimethylacetamide, toluene, p-xylene, and acetonitrile.
3. The method according to claim 1, wherein the nickel catalyst is one of nickel fluoride, nickel chloride, nickel bromide, nickel acetate, nickel sulfate, nickel acetate, nickel trifluoroacetate, nickel trifluoromethanesulfonate, nickel acetylacetonate, (1, 1' -bis (diphenylphosphino) ferrocene) dichloride nickel, and bis- (1, 5-cyclooctadiene) nickel, and the amount is 1 to 30 mol%.
4. The method according to claim 1, wherein the base is one of potassium carbonate, sodium carbonate, potassium bicarbonate, sodium bicarbonate, cesium carbonate, sodium tert-butoxide, and potassium tert-butoxide, in an amount of 2 to 5 equivalents.
5. The method according to claim 1, wherein the reaction is carried out at 25 to 160 ℃ for 1 to 48 hours.
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