Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO<sub>3</sub>
Tania Katsina, Louis Clavier, Jean-François Giffard, Nayane Macêdo Portela da Silva, Jean Fournier, Rodolphe Tamion, Chloé Copin, Stellios Arseniyadis, Alexandre Jean
Abstract
A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.
Topics & Concepts
ChemistryAllylic rearrangementCatalysisAlcohol oxidationMolecular oxygenCombinatorial chemistryOrganic chemistryOxygenOxidative Organic Chemistry ReactionsSynthetic Organic Chemistry MethodsTraditional and Medicinal Uses of Annonaceae