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. © The Royal Society of Chemistry 2015.