Copper-catalysed aerobic oxidation of alcohols using fluorous biphasic catalysis

A copper(I) catalysed and TEMPO mediated fluorous biphasic oxidation of primary, secondary, allylic and benzylic alcohols with oxygen in the presence of a bipyridine ligand bearing perfluorinated ponytails is described. High chemoselectivities are observed in the oxidation of substituted cyclohexanols (substituted axial cyclohexanols react 6–8 times faster than the corresponding equatorial cyclohexanols).