Ruthenium-catalyzed oxidative cleavage of olefins to aldehydes

D Yang; C Zhang

doi:10.1021/jo010122p

Ruthenium-catalyzed oxidative cleavage of olefins to aldehydes

J Org Chem. 2001 Jul 13;66(14):4814-8. doi: 10.1021/jo010122p.

Authors

D Yang¹, C Zhang

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong. yangdan@ku.hk

PMID: 11442410
DOI: 10.1021/jo010122p

Abstract

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).