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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...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2022
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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. |
format | Online Article Text |
id | pubmed-9457716 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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