Organic Chemistry Portal



Chemoselective Oxidation of p-Methoxybenzyl Ethers by an Electronically Tuned Nitroxyl Radical Catalyst

Shohei Hamada*, Koichi Sugimoto, Elghareeb E. Elboray, Takeo Kawabata, and Takumi Furuta

*Department of Pharmaceutical Chemistry, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8414, Japan, Email:

S. Hamada, K. Sugimoto, E. E. Elboray, T. Kawabata, T. Furuta, Org. Lett., 2020, 22, 5486-5490.

DOI: 10.1021/acs.orglett.0c01839

see article for more reactions


An oxidative deprotection of p-methoxy benzyl (PMB) ethers was achieved using a nitroxyl radical catalyst with electron-withdrawing ester groups adjacent to the nitroxyl group in the presence of 1 equiv of PIFA as co-oxidant. The corresponding carbonyl compounds were obtained in the presence of an excess of PIFA.

see article for more examples

Key Words

cleavage of ethers, phenyl iodonium bis(trifluoroacetate), organocatalysis

ID: J54-Y2020