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Remote C−H Activation of Quinolines through Copper‐Catalyzed Radical Cross‐Coupling
Author(s) -
Xu Jun,
Shen Chao,
Zhu Xiaolei,
Zhang Pengfei,
Ajitha Manjaly J.,
Huang KuoWei,
An Zhongfu,
Liu Xiaogang
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201501407
Subject(s) - sulfonyl , catalysis , radical , combinatorial chemistry , chemistry , surface modification , rational design , substrate (aquarium) , copper , functional group , photochemistry , molecule , hydrogen bond , nanotechnology , organic chemistry , materials science , alkyl , oceanography , geology , polymer
Achieving site selectivity in carbon–hydrogen (C−H) functionalization reactions is a formidable challenge in organic chemistry. Herein, we report a novel approach to activating remote C−H bonds at the C5 position of 8‐aminoquinoline through copper‐catalyzed sulfonylation under mild conditions. Our strategy shows high conversion efficiency, a broad substrate scope, and good toleration with different functional groups. Furthermore, our mechanistic investigations suggest that a single‐electron‐transfer process plays a vital role in generating sulfonyl radicals and subsequently initiating C−S cross‐coupling. Importantly, our copper‐catalyzed remote functionalization protocol can be expanded for the construction of a variety of chemical bonds, including C−O, C−Br, C−N, C−C, and C−I. These findings provide a fundamental insight into the activation of remote C−H bonds, while offering new possibilities for rational design of drug molecules and optoelectronic materials requiring specific modification of functional groups.