Synfacts 2009(4): 0445-0445  
DOI: 10.1055/s-0028-1088095
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Organocatalytic Oxidative Cleavage of C-C Double and Triple Bonds

Contributor(s): Benjamin List, Steffen Müller
K. Miyamoto, Y. Sei, K. Yamaguchi, M. Ochiai*
University of Tokushima and Tokushima Bunri University, Sanuki, Japan
Further Information

Publication History

Publication Date:
23 March 2009 (online)


The authors present further developments of their recently reported oxidative cleavage of C-C double bonds using aryl-λ³-iodanes as the catalytically active species (J. Am. Chem. Soc. 2007, 129, 2772). In the present work iodo-mesitylene (1) was used as organocatalyst for the cleavage of C-C double and triple bonds in the presence of aqueous HBF4 and MCPBA as the stoichi­ometric oxidant. The proposed mechanism involves oxidation of the olefin to the corresponding 1,2-diol 2, presumably forming a dialkoxy-λ³-iodane 3 with the dihydroxy-λ³-iodane 4, which is generated in situ from the catalyst 1 and MCPBA in the presence of aqueous HBF4. After the cleavage of 3 the resulting carbonyl compound is finally oxidized to the corresponding carboxylic acid.