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S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling

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Abstract

Sulfuric chloride is used as the source of the –SO2– 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.

Graphical abstract: S(vi) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling

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Article information


Submitted
08 Mar 2021
Accepted
05 Apr 2021
First published
06 Apr 2021

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2021, Advance Article
Article type
Edge Article

S(VI) in three-component sulfonamide synthesis: use of sulfuric chloride as a linchpin in palladium-catalyzed Suzuki–Miyaura coupling

X. Wang, M. Yang, S. Ye, Y. Kuang and J. Wu, Chem. Sci., 2021, Advance Article , DOI: 10.1039/D1SC01351C

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