Issue 40, 2015

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
26 Jan 2015
Accepted
16 Mar 2015
First published
16 Mar 2015

RSC Adv., 2015,5, 31584-31593

Author version available

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

D. Kumar, A. S. Singh and V. K. Tiwari, RSC Adv., 2015, 5, 31584 DOI: 10.1039/C5RA01545F

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