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.