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Oxidative Deprotection of p‑Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis

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journal contribution
posted on 2019-02-20, 00:00 authored by Deok Kyun Ahn, Young Woo Kang, Sang Kook Woo
An efficient and greener deprotection method for p-methoxybenzyl (PMB) ethers using a metal-free visible light photoredox catalyst and air and ammonium persulfate as the terminal oxidants is presented. Various functional groups and protecting groups were tolerated in the developed method to achieve good to excellent yields in short reaction times. Significantly, the developed method was compatible with PMB ethers derived from primary, secondary, and tertiary alcohols and a gram-scale reaction. Mechanistic studies support a proposed reaction mechanism that involves single electron oxidation of the PMB ether.