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The oxidation of p-methoxybenzyl (PMB) ethers was achieved using a 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 one equivalent of the co-oxidant phenyl iodonium bis(trifluoroacetate) (PIFA). This system showed an excellent chemoselectivity profile for the deprotection of PMB ethers from a broad range of functional groups including diverse oxidation-sensitive moieties. The corresponding carbonyl compounds were obtained by treating the PMB-protected alcohols with 1 and an excess amount of PIFA.

Oxidative Deprotection of <i>p</i>-Methoxybenzyl Ethers by a Nitroxyl Radical Catalyst