Electrosynthesis of Cyclic Isoureas and Ureas Through Contiguous Heterofunctionalizations

Abstract

An efficient synthetic protocol for the selenylated cyclic isoureas was developed using electrochemical activation of diselenides. This sustainable approach permitted transition metal and chemical oxidant-free difunctionalization of olefins and overall access to distinct 1,2,3 triheterofunctionalized carbon skeletons. Excellent functional group tolerance was noticed, allowing the synthesis of a series of cyclic isourea derivatives. In addition, an acid-triggered skeletal isomerization facilitated the synthesis of cyclic urea derivatives from the corresponding cyclic isoureas. Mechanistic investigations, along with voltammetric studies, enabled the postulation of the reaction mechanism.