A simple, base-free preparation of S-aryl thioacetates as surrogates for aryl thiols

Abstract

A mild method for the preparation of S-aryl thioacetates by hetero cross-coupling reactions of aryl bromides or aryl triflates with potassium thioacetate is described. The reaction proceeded smoothly in toluene at 110 °C, mediated by catalytic Pd 2(dba) 3 in combination with CyPF- tBu as the ligand. Neither the presence of a base nor microwave conditions were required. The formed S-aryl thioacetate proved to be stable under flash chromatographic conditions and could be rapidly converted into the corresponding thiol under mildly basic conditions.