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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...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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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. |
format | Online Article Text |
id | pubmed-5437376 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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
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title_full | Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
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title_fullStr | Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
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title_full_unstemmed | Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
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title_short | Mild, visible light-mediated decarboxylation of aryl carboxylic acids to access aryl radicals
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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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