Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System.

Abstract

A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.