Hidrocalcogenação de derivados de álcoois propargílicos mediados por calcogenolatos de zinco

Abstract

Organylzinc chalcogenolate mediated hydrochalcogenation of propargyl alcohols organylzinc chalcogenolate (chalcogen = sulfur, selenium and tellurium) prepared from the reductive cleavage of diorganyl dichalcogenide bonds by the Zn/NH4OH system led to organylzinc chalcogenolates that provide an alternative synthetic route to produce carbon-chalcogen bonds. This work presents new synthetic methodology and discusses the general aspects and limitations of organylzinc chalcogenolate to promote the hydrochalcogenetion of 2-alkyn-1-ol derivates leading mainly the Markovnikov allylic alcohols bearing a vinylic chalcogenide substituints. We investigated the chemo, regio- and stereoselctivity for this protocol in two different systems: in aqueous medium and in organic medium.