In the addition of stannyl- and silylcupration reagents to propargylic sulphides, the dependence of the regiochemistry of the adducts on the reaction conditions as well as on the nature of the Group 14 element in the metallo-metallation reagent, coupled with the possibility of a metal-mediated desulphuration path, can be exploited into a flexible method for the synthesis of a series of unsaturated organometallic derivatives.