期刊
CHEMISTRY-AN ASIAN JOURNAL
卷 11, 期 6, 页码 882-892出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.201501407
关键词
cross-coupling; remote C-H functionalization; radicals; sulfonylation
资金
- National Natural Science Foundation of China [21376058, 21302171]
- Zhejiang Provincial Natural Science Foundation of China [LZ13B 020001]
- Key-Sci-Tech Innovation Team of Zhejiang Province [2010R50017]
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.
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