Chemoselective Oxidation of<i>p</i>-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst
Shohei Hamada, Koichi Sugimoto, Elghareeb E. Elboray, Takeo Kawabata, Takumi Furuta
Abstract
The oxidation of p-methoxy benzyl (PMB) ethers was achieved using nitroxyl radical catalyst 1, which contains electron-withdrawing ester groups adjacent to the nitroxyl group. The oxidative deprotection of the PMB moieties on the hydroxy groups was observed upon treatment of 1 with 1 equiv of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess of PIFA.
Topics & Concepts
NitroxylChemistryCatalysisOxidative phosphorylationMedicinal chemistryPolymer chemistryOrganic chemistryBiochemistryOxidative Organic Chemistry ReactionsRadical Photochemical ReactionsVanadium and Halogenation Chemistry