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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...

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Autores principales: Wang, Xuefeng, Yang, Min, Ye, Shengqing, Kuang, Yunyan, Wu, Jie
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/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.
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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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