Cargando…

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Nguyen, Vu T., Haug, Graham C., Nguyen, Viet D., Vuong, Ngan T. H., Arman, Hadi D., Larionov, Oleg V.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
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
_version_ 1783691204487020544
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
work_keys_str_mv AT nguyenvut photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides
AT hauggrahamc photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides
AT nguyenvietd photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides
AT vuongnganth photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides
AT armanhadid photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides
AT larionovolegv photocatalyticdecarboxylativeamidosulfonationenablesdirecttransformationofcarboxylicacidstosulfonamides