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

Autor: Shohei Hamada, Elghareeb E. Elboray, Takumi Furuta, Koichi Sugimoto, Takeo Kawabata
Rok vydání: 2020
Předmět:
Zdroj: Organic Letters. 22:5486-5490
ISSN: 1523-7052
1523-7060
DOI: 10.1021/acs.orglett.0c01839
Popis: 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.
Databáze: OpenAIRE