Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 47, Pages 12259-12263Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201801466
Keywords
alcohols; formic acid; homogeneous catalysis; hydrogenolysis; palladium
Categories
Funding
- Fonds der Chemischen Industrie (Liebig fellowship, I.F.)
- Deutsche Bundesstiftung Umwelt
- University of Tubingen
- University of Tubingen: Deutsche Forschungsgemeinschaft [ZUK 63]
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We report the first homogeneous palladium-based transfer hydrogenolysis of benzylic alcohols using an in situ formed palladium-phosphine complex and formic acid as reducing agent. The reaction requires a catalyst loading as low as only 1 mol% of palladium and just a slight excess of reductant to obtain the deoxygenated alkylarenes in good to excellent yields. Besides demonstrating the broad applicability for primary, secondary and tertiary benzylic alcohols, a reaction intermediate could be identified. Additionally, it could be shown that partial oxidation of the applied phosphine ligand was beneficial for the course of the reaction, presumably by stabilizing the active catalyst. Reaction profiles and catalyst poisoning experiments were used to characterize the catalyst, the results of which indicate a homogeneous metal complex as the active species.
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