期刊
CHEMICAL SCIENCE
卷 9, 期 3, 页码 634-639出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/c7sc04086e
关键词
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资金
- National Natural Science Foundation of China [21572024]
- Natural Science Foundation of Jiangsu Province [BK20151184]
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology [BM2012110]
- Advanced Catalysis & Green Manufacturing Collaborative Innovation Center
An unprecedented dearomatization of indoles with diazoesters has been developed via cationic gold(I) catalysis. The functionalization selectively occurs at the C3-position to deliver methylene indole derivatives in good yields with excellent Z-selectivity, demonstrating unusual reactivity and selectivity compared with other noble metal catalysis. Importantly, simply followed by silica gel adsorption, an unprecedented metal-free aerobic oxidation occurs for indoles bearing N-electron donating substituents, providing a novel and efficient approach towards 3-substituted indolin-2-ones with a newly formed quaternary stereocenter in excellent stereoselectivity. Notably, these processes afford direct and selective access to a variety of valuable intermediates from abundant feedstock chemicals.
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