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

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.