Bioinspired o-Naphthoquinone-Catalyzed Aerobic Oxidation of Alcohols to Aldehydes and Ketones.

A biomimetic alcohol dehydrogenase (ADH)-like oxidation protocol was developed using an ortho-naphthoquinone catalyst in the presence of a catalytic amount of base. The developed organocatalytic aerobic oxidation protocol proceeds through the intramolecular 1,5-hydrogen atom transfer of naphthalene alkoxide intermediates, a mechanistically distinctive feature from the previous alcohol dehydrogenase mimics that require metals in the active form of catalysts. The ADH-like aerobic oxidation protocol should provide green alternatives to the existing stoichiometric and metal-catalyzed alcohol oxidation reactions.