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

Pieter Mampuys; Yanping Zhu; Tjøstil Vlaar; Eelco Ruijter; Romano V A Orru; Bert U W Maes

doi:10.1002/anie.201406717

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

Angew Chem Int Ed Engl. 2014 Nov 17;53(47):12849-54. doi: 10.1002/anie.201406717. Epub 2014 Sep 15.

Authors

Pieter Mampuys¹, Yanping Zhu, Tjøstil Vlaar, Eelco Ruijter, Romano V A Orru, Bert U W Maes

Affiliation

¹ Organic Synthesis, Department of Chemistry, University of Antwerp, Groenenborgerlaan 171, 2020 Antwerp (Belgium).

PMID: 25223494
DOI: 10.1002/anie.201406717

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amines / chemistry*
Cyanides / chemistry*
Molecular Structure
Sulfonic Acids / chemistry*
Thiourea / analogs & derivatives
Thiourea / chemical synthesis*
Thiourea / chemistry

Substances

Amines
Cyanides
Sulfonic Acids
Thiourea