Dzhemilev reaction in the synthesis of five-membered sulfur and selenium heterocycles

A one-pot methods were developed for the synthesis of five-membered sulfur and selenium heterocycles based on the consecutive cyclometallation of olefins, allenes, and acetylenes using alkyl and haloalkyl derivatives of Al and Mg in the presence of catalytic amounts of titanium and zirconium complexes to give the corresponding alumina- and magnesacarbocycles in situ, which, without further purification, were introduced into reaction with sulfur or selenium, leading to various tetrahydrothiophenes, thiophenes, tetrahydroselenophenes, and selenophenes.