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Issue 5, 2017
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Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals

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Abstract

Herein we present the first example of aryl radical formation via the visible light-mediated decarboxylation of aryl carboxylic acids using photoredox catalysis. This method constitutes a mild protocol for the decarboxylation of cheap and abundant aryl carboxylic acids and tolerates both electron-rich substrates and those lacking ortho-substitution. The in situ formation of an acyl hypobromite is proposed to prevent unproductive hydrogen atom abstraction and trapping of the intermediate aroyloxy radical, enabling mild decarboxylation.

Graphical abstract: Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals

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Article information


Submitted
18 Dec 2016
Accepted
27 Feb 2017
First published
27 Feb 2017

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2017,8, 3618-3622
Article type
Edge Article

Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals

L. Candish, M. Freitag, T. Gensch and F. Glorius, Chem. Sci., 2017, 8, 3618 DOI: 10.1039/C6SC05533H

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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