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Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling

We here have developed an S(O)(2)–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the...

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Autores principales: Liang, Zhipeng, Wu, Ya-Nan, Wang, Yang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457716/
https://www.ncbi.nlm.nih.gov/pubmed/36080306
http://dx.doi.org/10.3390/molecules27175539
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author Liang, Zhipeng
Wu, Ya-Nan
Wang, Yang
author_facet Liang, Zhipeng
Wu, Ya-Nan
Wang, Yang
author_sort Liang, Zhipeng
collection PubMed
description We here have developed an S(O)(2)–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields.
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spelling pubmed-94577162022-09-09 Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling Liang, Zhipeng Wu, Ya-Nan Wang, Yang Molecules Article We here have developed an S(O)(2)–N coupling between phenylsulfinic acid derivatives and aryl azides by dual copper and visible light catalysis. In this efficient and mild pathway, the reaction produces sulfonamide compounds under redox-neutral condition, which is mechanistically different from the nitrogen nucleophilic substitution reactions. Significantly, this transformation intends to utilize the property of visible light-induced azides to generate triplet nitrene and followed coupling with sulfonyl radicals in situ to achieve structurally diverse benzenesulfinamides in good yields. MDPI 2022-08-28 /pmc/articles/PMC9457716/ /pubmed/36080306 http://dx.doi.org/10.3390/molecules27175539 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Liang, Zhipeng
Wu, Ya-Nan
Wang, Yang
Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title_full Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title_fullStr Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title_full_unstemmed Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title_short Construction of Benzenesulfonamide Derivatives via Copper and Visible Light-induced Azides and S(O)(2)–H Coupling
title_sort construction of benzenesulfonamide derivatives via copper and visible light-induced azides and s(o)(2)–h coupling
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9457716/
https://www.ncbi.nlm.nih.gov/pubmed/36080306
http://dx.doi.org/10.3390/molecules27175539
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