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

Herein we present the first example of aryl radical formation 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 s...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2017-05, Vol.8 (5), p.3618-3622
Main Authors: Candish, L, Freitag, M, Gensch, T, Glorius, F
Format: Article
Language:English
Subjects:
Aromatic compounds
Carboxylic acids
Catalysis
Decarboxylation
Formations
Hydrogen atoms
Radicals
Trapping
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Summary:Herein we present the first example of aryl radical formation 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 -substitution. The formation of an acyl hypobromite is proposed to prevent unproductive hydrogen atom abstraction and trapping of the intermediate aroyloxy radical, enabling mild decarboxylation.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc05533h