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


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.

SUBMITTER: Candish L 

PROVIDER: S-EPMC5437376 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

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

Candish L L   Freitag M M   Gensch T T   Glorius F F  

Chemical science 20170227 5


Herein we present the first example of aryl radical formation <i>via</i> 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 <i>ortho</i>-substitution. The <i>in situ</i> formation of an acyl hypobromite is proposed to prevent unproductive hydrogen atom abstraction and trapping of the  ...[more]

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