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Synthesis 1996; 1996(11): 1341-1344
DOI: 10.1055/s-1996-4381
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Zirconium Alkoxide Catalyzed Oppenauer Oxidation Using Chloral as the Hydride Acceptor

Karsten Krohn* , Birgit Knauer, Jochen Küpke, Dieter Seebach, Albert K. Beck, Michyay Hayakawa
  • *Universität-GH Paderborn, FB 13, Fachgebiet Organische Chemie, Warburger Str. 100, D-33098 Paderborn, Fax +49(5251)603245; E-mail kk@chemi-uni-paderborn.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A new variation of the Oppenauer oxidation is presented with chloral as the hydride acceptor and Zr(O-t-BU)4 or, for highly reactive carbonyl products, the heterogeneous system SiO2/Zr(O-n-Pr)x, as the catalyst. The reaction proceeds under mild conditions (20°C) with a substoichiometric amount of Zr(O-t-Bu)4 (usually 20%). Primary and secondary allyl alcohols are converted in high yields to the corresponding carbonyl compounds.

Oppenauer oxidation - chloral - hydride transfer - Zr(O-t-Bu)4 catalysis - alcohols - aldehydes - ketones