Direct Transformation of Terminal Alkynes into Amidines by a Silver-Catalyzed Four-Component Reaction

An unprecedented conversion of terminal alkynes into N-sulfonimidamides (amidines) is reported by a silver-catalyzed, one-pot, four-component reaction with TMSN 3 , sodium sulfinate, and sulfonyl azide. The reaction scope includes both aromatic and aliphatic alkynes. A possible cascade reaction mechanism, consisting of alkyne hydroazidation, sulfonyl radical addition, 1,3-dipolar cycloaddition by TMSN 3 , and retro-1,3-dipolar cycloaddition, is proposed. TMSN 3 is found to play an essential role in each step of the reaction.