Nonmetal catalyzed hydrogenation of carbonyl compounds.

J Am Chem Soc

Department of Chemistry, Imperial College London, London SW7 2AZ, U.K.

Published: November 2014

Solutions of the Lewis acid B(C6F5)3 in 1,4-dioxane are found to effectively catalyze the hydrogenation of a variety of ketones and aldehydes. These reactions, the first to allow entirely metal-free catalytic hydrogenation of carbonyl groups under relatively mild reaction conditions, are found to proceed via a "frustrated Lewis pair" mechanism in which the solvent, a weak Brønsted base yet moderately strong donor, plays a pivotal role.

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http://dx.doi.org/10.1021/ja5088979DOI Listing

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