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Homogeneous Palladium‐Catalyzed Transfer Hydrogenolysis of Benzylic Alcohols Using Formic Acid as Reductant
Author(s) -
Ciszek Benjamin,
Fleischer Ivana
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801466
Subject(s) - hydrogenolysis , palladium , catalysis , chemistry , phosphine , formic acid , homogeneous catalysis , ligand (biochemistry) , organic chemistry , biochemistry , receptor
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.