Regioselective Markovnikov hydrothiolation of 1-aryl-1,3-butadienes with dithiocarbamic acid to allyl dithiocarbamates

Abstract

A metal, ligand and solvent-free three component reaction of 1-aryl-1,3-butadienes, CS₂ and amine has been developed. In this process, readily available CS₂ and secondary amines were used for C-N and C-S bonds giving allyl dithiocarbamates with notable Markovnikov selectivity, mild reaction conditions, simple operation and compatibility with various functional groups (37 examples). This is first case of dithiocarbamic acid addition to an unsymmetrical 1,3-diene system.