Issue 10, 2019

Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer

Abstract

An operationally simple photochemical strategy for the direct arylation of oxindoles with (hetero)aryl halides in the absence of both transition metals and photoredox catalysts has been developed. The reaction provides an efficient way to construct various 3-aryloxindole building blocks of pharmaceutical interest at ambient temperature by using household compact fluorescent light (CFL) bulbs as the light source. Preliminarily, mechanistic studies revealed that the intermolecular electron transfer relied on the formation of photon-absorbing electron–donor–acceptor (EDA) complexes between electron-rich oxindole enolates and electron-deficient (hetero)aryl halides, and a radical chain mechanism was operative.

Graphical abstract: Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Nov 2018
Accepted
20 Jan 2019
First published
22 Jan 2019
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., 2019,10, 3049-3053

Transition-metal-free α-arylation of oxindoles via visible-light-promoted electron transfer

K. Liang, N. Li, Y. Zhang, T. Li and C. Xia, Chem. Sci., 2019, 10, 3049 DOI: 10.1039/C8SC05170D

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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