Selective Oxidation of Unsaturated Alcohols Catalyzed by Sodium Nitrite and 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone with Molecular Oxygen under Mild Conditions

We have developed a simple and practical process for the oxidation of alcohols to the corresponding carbonyl compounds by using a low catalytic amount of DDQ, NaNO2 as a cocatalyst, and molecular oxygen as terminal oxidant. Nitric oxide generated in situ by NaNO2 in the presence of AcOH is essential for the realization of the catalytic cycle at room temperature. The practical utility of this catalytic process has been demonstrated in the gram-scale oxidation of cinnamyl alcohol.