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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 β‐organochalcogenacrylic acids and esters under mild basic conditions. The stereochemistry corresponded to anti‐Markovnikov addition of the organyl chalcogenolate constituents across the triple bond.

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