Highly stereoselective synthesis of N-sulfonyl amidines with calcium carbide as an acetylene source

Abstract

A practical and convenient approach for the highly stereoselective synthesis of N-sulfonyl amidines via a one-pot multi-component cascade reaction of sulfonyl azides, amines, water, and calcium carbide as an acetylene source has been developed, in which C–N and CN bonds are constructed simultaneously. The method exhibits a broad substrate scope (35 examples) with up to 93% yield and E/Z > 99 : 1. Some deuterated products are readily prepared when deuterium water is used as a reagent. This protocol features mild reaction conditions, simple operation, and ready scalability.