Dehydrogenation of inert alkyl groups via remote C-H activation:: Converting a propyl group into a π-allylic complex

Pd(OAC)(2)-inediated dehydrogenation of an alkyl group to a double bond or a eta(3)-allylic complex via sp(3) C-H bond activation and allylic oxidation is reported. A novel redox is Proposed for this double oxidation under oxidant-free conditions. A catalytic protocol using benzoquinone as the stoichiometric oxidant has also been developed for the dehydrogenation of cyclopentylcarboxamides.