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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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Publication details

The article was received on 18 Dec 2016, accepted on 27 Feb 2017 and first published on 27 Feb 2017


Article type: Edge Article
DOI: 10.1039/C6SC05533H
Citation: Chem. Sci., 2017, Advance Article
  • Open access: Creative Commons BY license
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    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, Advance Article , DOI: 10.1039/C6SC05533H

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