op9b00513_si_001.pdf (1.47 MB)
Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3
journal contribution
posted on 2020-03-17, 21:30 authored by Tania Katsina, Louis Clavier, Jean-François Giffard, Nayane Macedo Portela da Silva, Jean Fournier, Rodolphe Tamion, Chloé Copin, Stellios Arseniyadis, Alexandre JeanA 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.