Issue 3, 2018

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

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

Supplementary files

Article information

Article type
Edge Article
Submitted
18 Sep 2017
Accepted
04 Nov 2017
First published
06 Nov 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2018,9, 634-639

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

K. Liu, G. Xu and J. Sun, Chem. Sci., 2018, 9, 634 DOI: 10.1039/C7SC04086E

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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