Organylzinc Chalcogenolate Promoted Michael-Type Addition of α,β-Unsaturated Carbonyl Compounds

We present the chemo-, regio-, and stereoselective synthesis of vinyl chalcogenide compounds promoted by organylzinc chalcogenolates. In this protocol, reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzinc chalcogenolates. The reaction was performed with propiolic acids and esters and afforded -organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti-Markovnikov addition of the organyl chalcogenolate constituents across the triple bond.