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 degrees 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.
Synthetic scope of alcohol transfer dehydrogenation catalyzed by Cu/Al2O3: a new metallic catalyst with unusual selectivity / Federica Zaccheria, Nicoletta Ravasio, Rinaldo Psaro, Achille Fusi. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 12:24(2006), pp. 6426-6431. [10.1002/chem.200501619]
Synthetic scope of alcohol transfer dehydrogenation catalyzed by Cu/Al2O3: a new metallic catalyst with unusual selectivity.
F. Zaccheria;A. Fusi
2006
Abstract
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 degrees 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.Pubblicazioni consigliate
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