Electrochemical Stereoselective Synthesis of (Z)-Allyl Aryl Selenides and Sulfides from Baylis-Hillman Acetates

This research presents a method for the oxidative selenylation and thiolylation of Morita-Baylis-Hillman adducts through constant-current electrolysis in an undivided cell at room temperature. The reaction enables direct production of trisubstituted (Z)-allyl aryl selenides and sulfides with yields of 27-98%. A wide variety of different functionalities are well tolerated under these reaction conditions. This strategy could be carried out on gram scale and several synthetic transformations were accomplished for the construction of other allyl selenide derivatives. Control experiments and mechanistic studies indicate a radical or an ionic addition pathway for this electrochemical transformation.