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Selective Base-free Transfer Hydrogenation of α,β-Unsaturated Carbonyl Compounds using iPrOH or EtOH as Hydrogen
Ronald A Farrar-Tobar1, Zhihong Wei1, Haijun Jiao1
1Leibniz Institut für Katalyse e. V. an der, Universität Rostock, Albert-Einstein-Straße 29a, 18055, Rostock, Germany.
Abstract:
Commercially available Ru-MACHOTM -BH is an active catalyst for the hydrogenation of several functional groups and for the dehydrogenation of alcohols. Herein, we report on the new application of this catalyst to the base-free transfer hydrogenation of carbonyl compounds. Ru-MACHOTM -BH proved to be highly active and selective in this transformation, even with α,β-unsaturated carbonyl compounds as substrates. The corresponding aliphatic, aromatic and allylic alcohols were obtained in excellent yields with catalyst loadings as low as 0.1-0.5 mol % at mild temperatures after very short reaction times. This protocol tolerates iPrOH and EtOH as hydrogen sources. Additionally, scale up to multi-gram amounts was performed without any loss of activity or selectivity. An outer-sphere mechanism has been proposed and the computed kinetics and thermodynamics of crotonaldehyde and 1-phenyl-but-2-en-one are in perfect agreement with the experiment.
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