An unprecedented deoxygenation protocol of benzylic alcohols using bis(1-benzotriazolyl)methanethione

Abstract

A facile and regioselective two-step protocol for the deoxygenation of benzylic alcohols using bis(benzotriazole)methanethione has been devised. Benzotriazole derivatives, namely, benzyloxythioacylbenzotriazoles (ROCSBt), on reaction with silanes or Bu₃SnH under microwave irradiation or conventional heating undergo a free radical β-scission of C–O bond instead of N–N bond (benzotriazole ring cleavage) to afford a deoxy product. The methodology has various applications because it selectively deoxygenates benzylic alcohols with the aid of a relatively nontoxic (TMS)₃SiH reagent as an acceptable alternate to Bu₃SnH.