Nitrate as a Redox Co-Catalyst for the Aerobic Pd-Catalyzed Oxidation of Unactivated sp(3)-C-H Bonds.

This paper describes a new method for the catalytic aerobic oxygenation of unactivated sp(3)-C-H bonds. This transformation utilizes Pd(OAc)(2) as a catalyst in conjunction with NaNO(3) as a redox co-catalyst. Both oxime ether and pyridine derivatives are effective directing groups for these reactions. The oxygen incorporated into the product derives from the solvent (acetic acid). Preliminary results show that the addition of simple NaCl to the reaction mixture results in aerobic chlorination under analogous conditions.