Issue 13, 2024

Copper-catalyzed sulfonamidation of enol silyl ether via SO2 insertion towards the synthesis of β-keto sulfonamides

Abstract

A copper-catalyzed three-component sulfonation reaction utilizing enol silyl ether, N-acyloxyamine, and sulfur dioxide is introduced. This method provides a convenient and straightforward pathway to synthesize a variety of structurally diverse β-keto sulfonamides with satisfactory yields under mild reaction conditions. The protocol exhibits broad substrate compatibility and demonstrates good tolerance towards a variety of functional groups. Additionally, the successful execution of this reaction on a gram scale and the demonstration of several transformations with β-keto sulfonamides underscore the method's practical applicability. Preliminary mechanistic studies suggest that this transformation may involve a radical process.

Graphical abstract: Copper-catalyzed sulfonamidation of enol silyl ether via SO2 insertion towards the synthesis of β-keto sulfonamides

Supplementary files

Article information

Article type
Research Article
Submitted
21 Mar 2024
Accepted
28 Apr 2024
First published
15 May 2024

Org. Chem. Front., 2024,11, 3589-3595

Copper-catalyzed sulfonamidation of enol silyl ether via SO2 insertion towards the synthesis of β-keto sulfonamides

Q. Zeng, Y. Gong, X. Zhang and Z. Lian, Org. Chem. Front., 2024, 11, 3589 DOI: 10.1039/D4QO00523F

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