Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids

Dan Yang; Fei Chen; Ze-Min Dong; Dan-Wei Zhang

doi:10.1021/jo0357925

Ruthenium-catalyzed oxidative cleavage of alkynes to carboxylic acids

J Org Chem. 2004 Mar 19;69(6):2221-3. doi: 10.1021/jo0357925.

Authors

Dan Yang¹, Fei Chen, Ze-Min Dong, Dan-Wei Zhang

Affiliation

¹ Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China. [email protected]

PMID: 15058980
DOI: 10.1021/jo0357925

Abstract

We describe an efficient method for the oxidative cleavage of alkynes to carboxylic acids using a combination of RuO(2)/Oxone/NaHCO(3) in a CH(3)CN/H(2)O/EtOAc solvent system. Both internal and terminal alkynes, regardless of their electron density, can be oxidized to carboxylic acids in excellent yield (up to 99%). (1)H NMR spectroscopy and ESI-MS experiments provided evidence for alpha-diketones and anhydrides as possible intermediates in these oxidation reactions.