Discovery, scope, and limitations of an N-dealkylation/N-arylation of secondary sulfonamides under Chan–Lam conditions

Abstract

We report the discovery, scope, and limitations of a Cu‐mediated sulfonamide N‐dealkylation/N‐arylation reaction. Specific secondary N‐alkyl sulfonamides undergo Cu‐mediated oxidative dealkylation followed by N‐arylation under Chan–Lam conditions. The reaction is relatively general, allowing the synthesis of a range of N‐aryl secondary sulfonamides in good yield. Mechanistic investigations determined the sequence of reaction events as well as the efficiency‐limiting events. Limitations in the methodology are also presented.