铜金属配合物和质子酸在可见光下催化喹啉与异喹啉的偶联反应  

Coupling reaction of quinoline with isoquinoline catalyzed by copper complex and protonic acid under visible light

作　　者：张金相 王琳 武可书[1,2,3] 刘鲲 王斌[1,2,3] ZHANG Jinxiang;WANG Lin;WU Keshu;LIU Kun;WANG Bin(College of Chemistry,Tianjin Normal University,Tianjin 300387,China;Key Laboratory of Inorganic-Organic Hybrid Functional Material Chemistry,Ministry of Education,Tianjin Normal University,Tianjin 300387,China;Tianjin Key Laboratory of Structure and Performance for Functional Molecules,Tianjin Normal University,Tianjin 300387,China)

机构地区：[1]天津师范大学化学学院,天津300387 [2]天津师范大学无机-有机杂化功能材料化学教育部重点实验室,天津300387 [3]天津师范大学天津市功能分子结构与性能重点实验室,天津300387

出　　处：《天津师范大学学报（自然科学版）》2018年第4期28-32,共5页Journal of Tianjin Normal University：Natural Science Edition

基　　金：国家自然科学基金资助项目(21102101;21172173)

摘　　要：为了优化喹啉和异喹啉化合物的偶联反应,降低反应成本,以可见光为能源,2,9-二甲基-4,7-二苯基-1,10-邻菲啰啉碳硼烷双二苯基膦一价铜配合物(Cu1)和质子酸为双催化剂,引发2-甲基喹啉和N-苯基四氢异喹啉的偶联反应.最佳反应条件为:催化剂Cu1的用量为3.0μmol,质子酸的种类为间甲基苯甲酸,其用量为6.0μmol,溶剂为甲醇与乙腈的等体积混合物(各1.0 mL),反应时间为35 h.在此条件下,选用分别带有不同取代基的2-甲基喹啉和四氢异喹啉为反应底物,成功合成了15种化合物,产率为27%~91%.结果表明,在Cu1和质子酸的催化下,可见光可以成功引发喹啉和异喹啉的偶联反应.In order to optimize the coupling reaction of quinoline with isoquinoline compounds and reduce the cost of the reaction,2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline-carboranebis（diphenylphosphine） monovalent copper complexes（Cu1）and protonic acid were used as double catalysts and visible light was adopted as the energy source,which can drive the coupling reaction of 2-methylquinoline and N-phenyl-tetrahydroisoquinoline. The optimum reaction conditions are as follows：the amount of catalyst Cu1 is 3.0 μmol,the type of proton acid is m-toluic acid and its dosage is 6.0 μmol,and the solvent is a mixture of methanol and acetonitrile with equal volume（1.0 mL each）,the reaction time is 35 h.Fifteen compounds were successfully synthesized with different substituent groups of 2-methylquinoline and N-phenyl-te-trahydroisoquinoline as the reactants. The yields ranged from 27 % to 91%. These results indicate that visible light can ini-tiate the coupling reaction of quinoline with isoquinoline catalyzed by Cu1 and protonic acid.

关 键 词：铜配合物 可见光 2-甲基喹啉 N-苯基四氢异喹啉 偶联反应 

分 类 号：O634[理学—高分子化学]