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Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides
Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functi...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2021
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115300/ https://www.ncbi.nlm.nih.gov/pubmed/34084443 http://dx.doi.org/10.1039/d1sc01389k |
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author | Nguyen, Vu T. Haug, Graham C. Nguyen, Viet D. Vuong, Ngan T. H. Arman, Hadi D. Larionov, Oleg V. |
author_facet | Nguyen, Vu T. Haug, Graham C. Nguyen, Viet D. Vuong, Ngan T. H. Arman, Hadi D. Larionov, Oleg V. |
author_sort | Nguyen, Vu T. |
collection | PubMed |
description | Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functionalized sulfonamides has remained elusive. Herein, we present a visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that is catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur–nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents. |
format | Online Article Text |
id | pubmed-8115300 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81153002021-06-02 Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides Nguyen, Vu T. Haug, Graham C. Nguyen, Viet D. Vuong, Ngan T. H. Arman, Hadi D. Larionov, Oleg V. Chem Sci Chemistry Sulfonamides feature prominently in organic synthesis, materials science and medicinal chemistry, where they play important roles as bioisosteric replacements of carboxylic acids and other carbonyls. Yet, a general synthetic platform for the direct conversion of carboxylic acids to a range of functionalized sulfonamides has remained elusive. Herein, we present a visible light-induced, dual catalytic platform that for the first time allows for a one-step access to sulfonamides and sulfonyl azides directly from carboxylic acids. The broad scope of the direct decarboxylative amidosulfonation (DDAS) platform is enabled by the efficient direct conversion of carboxylic acids to sulfinic acids that is catalyzed by acridine photocatalysts and interfaced with copper-catalyzed sulfur–nitrogen bond-forming cross-couplings with both electrophilic and nucleophilic reagents. The Royal Society of Chemistry 2021-04-13 /pmc/articles/PMC8115300/ /pubmed/34084443 http://dx.doi.org/10.1039/d1sc01389k Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Nguyen, Vu T. Haug, Graham C. Nguyen, Viet D. Vuong, Ngan T. H. Arman, Hadi D. Larionov, Oleg V. Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title | Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title_full | Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title_fullStr | Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title_full_unstemmed | Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title_short | Photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
title_sort | photocatalytic decarboxylative amidosulfonation enables direct transformation of carboxylic acids to sulfonamides |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115300/ https://www.ncbi.nlm.nih.gov/pubmed/34084443 http://dx.doi.org/10.1039/d1sc01389k |
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