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Synthetic Scope of Alcohol Transfer Dehydrogenation Catalyzed by Cu/Al 2 O 3 : A New Metallic Catalyst with Unusual Selectivity
Author(s) -
Zaccheria Federica,
Ravasio Nicoletta,
Psaro Rinaldo,
Fusi Achille
Publication year - 2006
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.200501619
Subject(s) - dehydrogenation , selectivity , catalysis , chemistry , allylic rearrangement , cyclohexanol , alcohol , styrene , alcohol oxidation , acceptor , substrate (aquarium) , hydrogen , transfer hydrogenation , photochemistry , organic chemistry , ruthenium , physics , oceanography , geology , copolymer , condensed matter physics , polymer
A method for the anaerobic oxidation of a wide series of alcohols including cyclohexanols and steroidal alcohols, has been set up. It relies on a transfer dehydrogenation reaction from the substrate alcohol to styrene catalyzed by a heterogeneous, reusable copper catalyst under very mild liquid‐phase experimental conditions (90 °C, N 2 ) and shows unusual selectivity. Thus, the method is selective for the oxidation of secondary and allylic alcohols even in the presence of unprotected primary and benzylic alcohols. Electronic effects and the choice of the hydrogen acceptor account for the selectivity observed.