title: 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.
authors.affiliation: Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium).
authors.forename: Pieter
authors.initials: P
authors.lastname: Mampuys
authors.forename: Yanping
authors.initials: Y
authors.lastname: Zhu
authors.forename: Tjøstil
authors.initials: T
authors.lastname: Vlaar
authors.forename: Eelco
authors.initials: E
authors.lastname: Ruijter
authors.forename: Romano V A
authors.initials: RV
authors.lastname: Orru
authors.forename: Bert U W
authors.initials: BU
authors.lastname: Maes
mesh_terms: D000588:Amines / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D015394:Molecular Structure; D013451:Sulfonic Acids / Q000737:chemistry*; D013890:Thiourea / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D003486:Cyanides; D013451:Sulfonic Acids; D013890:Thiourea
keywords: Lewis acids; copper catalysis; isocyanides; isothioureas; molecular sieves