Innovative carbon radical generation from hydrocarbons through a catalytic process under mild conditions has been achieved by the use of N-hydroxyphthalimide (NHPI) as a catalyst. This method can be successfully applied to a wide variety of functionalizations of hydrocarbons. Thus, alkanes are converted into alcohols, ketones, and carboxylic acids, through alkyl radicals generated by the action of NHPI. Cyclohexane was directly converted into adipic acid with O-2 by NHPI combined with Mn(OAC)(2). p-Xylene was oxidized to terephthalic acid in 95% yield by using an NHPI analogue as a catalyst. Alkenes could be epoxidized with H2O2 generated in situ from benzhydrol and O-2 under the influence of NHPI. (C) 2006 Elsevier B.V. All rights reserved.