Mild and efficient rhodium-catalyzed deoxygenation of ketones to alkanes

Abstract

A new and simple method for the deoxygenation of ketones to alkanes is presented. Most substrates are reduced under mild conditions by triethylsilane in the presence of catalytic amounts of [Rh(μ-Cl)(CO)₂]₂. This system selectively provides the methylene hydrocarbons in good to excellent yields starting from acetophenones and diaryl ketones. A rapid examination of the reaction pathway suggests that the ketone is first converted into an alcohol, which then undergoes hydrogenolysis to give the alkane.