Electrocatalytic Desulfurizative Amination of Thioureas to Guanidines.

Abstract

Guanidine has been known as an important class of N-containing molecules with a wide range of applications. Described here is a selective and efficient electrochemical approach to the synthesis of guanidines from easily accessible thioureas and amines. The key to success for this reaction is the in situ generation of a hypervalent iodine reagent as a catalyst from iodoarene by anodic oxidation. This mild desulfurizative amination presents ample substrate scope and good functional group tolerance without the use of extra stoichiometric chemical oxidants. As only electrons serve as the oxidation reagents, this method offers a more straightforward and sustainable manner toward versatile guanidines, including late-stage functionalization of pharmaceutically relevant molecules.