88615-22-9Relevant academic research and scientific papers
Sustainable three-component synthesis of isothioureas from isocyanides, thiosulfonates, and amines
Mampuys, Pieter,Zhu, Yanping,Vlaar, Tj?stil,Ruijter, Eelco,Orru, Romano V. A.,Maes, Bert U. W.
supporting information, p. 12849 - 12854 (2016/02/18)
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. Safety first! A direct synthesis of isothioureas by a copper-catalyzed three-component reaction from readily available substrates (see scheme) avoids the toxic, flammable, and highly reactive reagents required in classical approaches. The reaction also enables the straightforward synthesis of S-aryl isothioureas, which are difficult to obtain by other methods.
