Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling

Jun Xu, Chao Shen, Xiaolei Zhu, Pengfei Zhang, Manjaly John Ajitha, Kuo-Wei Huang, Zhongfu An, Xiaogang Liu

Research output: Contribution to journalArticlepeer-review

109 Scopus citations

Abstract

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. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Original languageEnglish (US)
Pages (from-to)882-892
Number of pages11
JournalChemistry - An Asian Journal
Volume11
Issue number6
DOIs
StatePublished - Feb 4 2016

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