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

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-ri...

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Detalles Bibliográficos
Autores principales: Candish, L., Freitag, M., Gensch, T., Glorius, F.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5437376/
https://www.ncbi.nlm.nih.gov/pubmed/28580100
http://dx.doi.org/10.1039/c6sc05533h
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author Candish, L.
Freitag, M.
Gensch, T.
Glorius, F.
author_facet Candish, L.
Freitag, M.
Gensch, T.
Glorius, F.
author_sort Candish, L.
collection PubMed
description 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.
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spelling pubmed-54373762017-06-02 Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals Candish, L. Freitag, M. Gensch, T. Glorius, F. Chem Sci Chemistry 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. Royal Society of Chemistry 2017-05-01 2017-02-27 /pmc/articles/PMC5437376/ /pubmed/28580100 http://dx.doi.org/10.1039/c6sc05533h Text en This journal is © The Royal Society of Chemistry 2017 http://creativecommons.org/licenses/by/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 Unported License (http://creativecommons.org/licenses/by/3.0/) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
spellingShingle Chemistry
Candish, L.
Freitag, M.
Gensch, T.
Glorius, F.
Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title_full Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title_fullStr Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title_full_unstemmed Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title_short Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
title_sort mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5437376/
https://www.ncbi.nlm.nih.gov/pubmed/28580100
http://dx.doi.org/10.1039/c6sc05533h
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