This article presents a method for the selectively oxidation of the secondary hydroxyl group into the corresponding keto-carbonyl group. The complex \[(neocuproine)Pd(OAc)\]2(OTf)2 synthesized from neocuproine (2,9-dimethyl-1,10-phenanthroline), HOTf and Pd(OAc)2, was used as a catalyst to the selective oxidation of several vicinal polyols with p-benzoquinone or O2 as oxidant by using the mixture of acetonitrile and water (9∶1) as a solvent. This catalytic system was applied to the oxidation of several vicinal polyols including 1,2-O-isopropylidene-α-D-glucofuranose, 1-phenylethane-1,2-diol and 1,2-decanediol to afford corresponding α-hydroxy ketones in good yields. Especially for the selective oxidation of 1-phenylethane-1,2-diol, the chemical yield was up to 93.0%.

vicinal polyols; palladium catalyst;chemoselective oxidation