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.