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Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles

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Abstract

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.

Graphical abstract: Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles

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Publication details

The article was received on 18 Sep 2017, accepted on 04 Nov 2017 and first published on 06 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC04086E
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY license
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    Gold-catalyzed stereoselective dearomatization/metal-free aerobic oxidation: access to 3-substituted indolines/oxindoles

    K. Liu, G. Xu and J. Sun, Chem. Sci., 2018, Advance Article , DOI: 10.1039/C7SC04086E

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