Chemoselective Hydrogenation of Nitro Compounds with Supported Gold Catalysts

The selective reduction of a nitro group when other reducible functions are present is a difficult process that often requires stoichiometric amounts of reducing agents or, if H2 is used, the addition of soluble metals. Gold nanoparticles supported on TiO2 or Fe2O3 catalyzed the chemoselective hydrogenation of functionalized nitroarenes with H2 under mild reaction conditions that avoided the accumulation of hydroxylamines and their potential exothermic decomposition. These chemoselective hydrogenation gold catalysts also provide a previously unknown route for the synthesis of the industrially relevant cyclohexanone oxime from 1-nitro-1-cyclohexene.