Chemoselective Transfer Hydrogenation of Nitroarenes with Ammonia Borane Catalyzed by Copper N-Heterocyclic Carbene Complexes  

作　　者：Hui Zhou Hongmei Jiao Xing Lu Yuanyuan Gao Zhiqiang Ren Haojie Ma Yuqi Zhang Bo Han 

机构地区：[1]Laboratory of New Energy&New Function Materials,Shaanxi Key Laboratory of Chemical Reaction Engineering,College of Chemistry and Chemical Engineering,Yan'an University,Yan'an,Shaanxi 716000,China

出　　处：《Chinese Journal of Chemistry》2024年第15期1721-1726,共6页中国化学（英文版）

基　　金：financial support from the National Natural Science Foundation of China(22061041);Key Project of Science&Technology of Shaanxi Province(2023-YBGY-430);Project of Science&Technology Bureau of Yulin City(CXY-2022-185);Doctoral Research Foundation of Yan'an University(YDBK2019-60);the Training Program of Innovation and Entrepreneurship for Undergraduates of Yan'an University(D2022077);Research Program of Yan'an University(YDY2020-61);the Youth Innovation Team Project of Shaanxi Provincial Education Department(No.23JP193);National Science Foundation of Shaanxi Province(S2023-JC-QN-0079).

摘　　要：Herein,we present a method for the homogeneous hydrogenation of nitroarenes to produce anilines using low catalyst loading(1 mo%)of copper N-heterocyclic carbene complexes as the catalyst and ammonia borane as the source of hydrogen.A wide range of nitroarenes,featuring diverse functional groups,were selectively transformed into their corresponding primary aromatic amines with high yields.This process can be readily scaled up and exhibits compatibility with various sensitive functional groups,including halogen,trifluoromethyl,aminomethyl,alkenyl,cyano,ester,amide,and hydroxyl.Notably,this catalytic methodology finds application in the synthesis of essential drug compounds.Mechanistic investigations suggest that the in-situ-generated Cu-H species may serve as active intermediates,with reduction pathways involving species such as azobenzene,1,2-diphenylhydrazine,nitrosobenzene,and N-phenylhydroxylamine.

关 键 词：Homogeneous catalysis HYDROGENATION N-Heterocyclic carbene complexes NITROARENES Ammonia borane 

分 类 号：O62[理学—有机化学]