Direct Synthesis of N-Acyl Sulfonimidamides and NSulfonimidoyl Amidines from Sulfonimidoyl Azides

Abstract

Herein, we describe the preparation of sulfonimidoyl azides, and demonstrate their utility in the construction of N-acyl sulfonimidamides and Nsulfonimidoyl amidines. N-Acyl sulfonimidamides were synthesized in good to very good yields via “on water” copper-catalyzed three-component coupling between sulfonimidoyl azide, alkynes and water. The use of amines as nucleophiles yielded a wide range of N-sulfonimidoyl amidines. Both reactions were completed in very short time at room temperature under mild conditions, thus establishing the potential of sulfonimidoyl azides, the aza-analogues of sulfonyl azides, as an excellent precursor to derive functionalized sulfonimidamides in one step.