Sustainable three-component synthesis of isothioureas from isocyanides, thiosulfonates, and amines

Abstract

Multiple applications of isothioureas as fine chemicals (or their precursors) are known, but a general sustainable method for their synthesis was hitherto unavailable. We report a novel general approach towards S-alkyl and S-aryl isothioureas through a copper(I)-catalyzed three-component reaction between amines, isocyanides, and thiosulfonates. The formal synthesis of a superpotent sweetener further illustrates the applicability of our method.

Keywords: Lewis acids; copper catalysis; isocyanides; isothioureas; molecular sieves.