TiCl4-mediated deoxygenative reduction of aromatic ketones to alkylarenes with ammonia borane

Abstract

A rapid and mild protocol for the exhaustive deoxygenation of various aromatic ketones to corresponding alkanes was described, which was mediated by TiCl₄ and used ammonia borane (AB) as the reductant. This reduction protocol applies to a wide range of substrates in moderate to excellent yields at room temperature. The gram-scale reaction and syntheses of some key building blocks for SGLT2 inhibitors demonstrated the practicability of this methodology. Preliminary mechanistic studies revealed that the ketone is first converted into an alcohol, which then undergoes a carbocation to give the alkane via hydrogenolysis.