Pd nanoparticles as catalysts for green and sustainable oxidation of functionalized alcohols in aqueous media

The previously described catalyst system for the aerobic oxidation of alcohols, comprising palladium(II) acetate in combination with neocuproine in a 1:1 mixture of water and a water-miscible cosolvent such as ethylene carbonate or dimethylsulfoxide, was shown to involve palladium nanoparticles as the active catalyst. The latter are formed in situ or can be preformed by reduction of the palladium-neocuproine complex with hydrogen and they are stabilized by both the neocuproine ligand and the cosolvent. This catalyst system was successfully used for the selective aerobic oxidation of the steroidal secondary alcohols, nandrolone and 5 alpha-pregnan-3 alpha-ol-20-one, to the corresponding ketones. (C) 2009 Elsevier Ltd All rights reserved.