Mild and Practical Dirhodium(II)/NHPI-Mediated Allylic and Benzylic Oxidations with Air as the Oxidant.

Aerobic allylic and benzylic oxidations catalyzed by dirhodium(II) complexes with N-hydroxyphthalimide (NHPI) are described. The open flask reaction occurs at mild temperature, using air as the oxidant. Mechanistic studies suggest that dirhodium(II) complexes axially coordinate with NHPI to activate the O-H bond in NHPI and decrease the bond-dissociation energy (BDE).