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S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling
Sulfuric chloride is used as the source of the –SO(2)– group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki–Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent re...
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/PMC8115270/ https://www.ncbi.nlm.nih.gov/pubmed/34084444 http://dx.doi.org/10.1039/d1sc01351c |
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author | Wang, Xuefeng Yang, Min Ye, Shengqing Kuang, Yunyan Wu, Jie |
author_facet | Wang, Xuefeng Yang, Min Ye, Shengqing Kuang, Yunyan Wu, Jie |
author_sort | Wang, Xuefeng |
collection | PubMed |
description | Sulfuric chloride is used as the source of the –SO(2)– group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki–Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. |
format | Online Article Text |
id | pubmed-8115270 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2021 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-81152702021-06-02 S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling Wang, Xuefeng Yang, Min Ye, Shengqing Kuang, Yunyan Wu, Jie Chem Sci Chemistry Sulfuric chloride is used as the source of the –SO(2)– group in a palladium-catalyzed three-component synthesis of sulfonamides. Suzuki–Miyaura coupling between the in situ generated sulfamoyl chlorides and boronic acids gives rise to diverse sulfonamides in moderate to high yields with excellent reaction selectivity. Although this transformation is not workable for primary amines or anilines, the results show high functional group tolerance. With the solving of the desulfonylation problem and utilization of cheap and easily accessible sulfuric chloride as the source of sulfur dioxide, redox-neutral three-component synthesis of sulfonamides is first achieved. The Royal Society of Chemistry 2021-04-06 /pmc/articles/PMC8115270/ /pubmed/34084444 http://dx.doi.org/10.1039/d1sc01351c Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by/3.0/ |
spellingShingle | Chemistry Wang, Xuefeng Yang, Min Ye, Shengqing Kuang, Yunyan Wu, Jie S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title | S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title_full | S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title_fullStr | S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title_full_unstemmed | S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title_short | S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling |
title_sort | s(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed suzuki–miyaura coupling |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8115270/ https://www.ncbi.nlm.nih.gov/pubmed/34084444 http://dx.doi.org/10.1039/d1sc01351c |
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