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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 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 ...[more]

PMID: 28580100

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