Electrochemical, Regioselective, and Stereoselective Synthesis of Allylic Thioethers and Selenoethers under Transition-Metal-Free and Oxidant-Free Conditions

Abstract

We disclose a mild, scalable, electricity-promoted cross coupling protocol between allylic iodides and disulfides/ diselenides for the formation of C−S/Se bonds in the absence of transition metals, bases, and oxidants. The stereochemically different densely functionalized allylic iodides gave regio-and stereoselective diverse thioethers in good yields. This strategy demonstrates a sustainable promising approach for the synthesis of allylic thioethers in 38−80% yields. This protocol also provides a synthetic platform for the synthesis of allylic selenoethers. A single-electron transfer radical pathway was also validated with radical scavenger experiments and cyclic voltammetry data.