Tandem base-free synthesis of β-hydroxy sulphides under ultrasound irradiation

Abstract

Rongalite® promotes cleavage of diaryl disulphides generating the corresponding thiolate species in situ which then undergo facile ring-opening of epoxides in a regioselective manner under ultrasound irradiation, affording β-hydroxy sulphides in good to excellent yields. The important features of this methodology are base-free, odourless, high yield, reasonably rapid reaction rate, simple workup, high regioselectivity, cost-effective and no requirement of transition metal catalysts. It is noteworthy that ring-opening reaction of 1,2-diphenyldiselane with 2-(phenoxymethyl)oxirane are also conducted smoothly to afford β-hydroxy selenide in excellent yield under the standard conditions. Rongalite® promotes ring-opening reaction of epoxides with diaryl disulphides or 1,2-diphenyldiselane with high regioselectivity under ultrasound irradiation. As a result, a set of the corresponding β-hydroxy sulphides or β-hydroxy selenides were obtained in good to excellent yields.