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- Title
Remote C−H Activation of Quinolines through Copper-Catalyzed Radical Cross-Coupling.
- Authors
Xu, Jun; Shen, Chao; Zhu, Xiaolei; Zhang, Pengfei; Ajitha, Manjaly J.; Huang, Kuo ‐ Wei; An, Zhongfu; Liu, Xiaogang
- 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.
- Subjects
QUINOLINE; CATALYSIS synthesis; COPPER research; DRUG microbiology; OPTOELECTRONIC devices
- Publication
Chemistry - An Asian Journal, 2016, Vol 11, Issue 6, p882
- ISSN
1861-4728
- Publication type
Article
- DOI
10.1002/asia.201501407