Ruthenium-Catalyzed Oxidative Cleavage of Olefins to Aldehydes

Dan Yang* and Chi Zhang
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong
J. Org. Chem., 2001, 66 (14), pp 4814–4818
DOI: 10.1021/jo010122p
Publication Date (Web): June 20, 2001
Copyright © 2001 American Chemical Society
*

 To whom correspondence should be addressed. Fax:  +852-2859-2159.

, yangdan@hku.hk

Abstract

Abstract Image

Three oxidation protocols have been developed to cleave olefins to carbonyl compounds with ruthenium trichloride as catalyst (3.5 mol %). These methods convert olefins that are not fully substituted to aldehydes rather than carboxylic acids. While aryl olefins were cleaved to aromatic aldehydes in excellent yields by using the system of RuCl3−Oxone−NaHCO3 in CH3CN−H2O (1.5:1), aliphatic olefins were converted into alkyl aldehydes with RuCl3−NaIO4 in 1,2-dichloroethane−H2O (1:1) in good to excellent yields. It is noteworthy that terminal aliphatic olefins were cleaved to the corresponding aldehydes in excellent yields by using RuCl3−NaIO4 in CH3CN−H2O (6:1).

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History

  • Published In Issue July 13, 2001
  • Received January 31, 2001

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