posted on 2020-03-17, 21:30authored byTania Katsina, Louis Clavier, Jean-François Giffard, Nayane Macedo Portela da Silva, Jean Fournier, Rodolphe Tamion, Chloé Copin, Stellios Arseniyadis, Alexandre Jean
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.