Catalyst-Controlled Dual Reactivity of Sulfonimidamides: Synthesis of Propargylamines and N-Propargyl Sulfonimidamides

Abstract

Sulfonimidamides (SIAs) are acting both as surrogate amines and nucleophiles depending on the reaction conditions to access propargylamines and N‐propargyl SIAs, respectively. The amine part of SIAs has been cleaved in an InCl3‐catalyzed three‐component A3 coupling reaction with aldehyde and acetylene to yield propargylamine. Moreover, N‐propargyl SIAs were obtained via the direct‐imination of propargyl alcohols in the presence of BF3⋅OEt2.