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Published on: May 21, 2019
Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
Deok Kyun Ahn1, Young Woo Kang1, Sang Kook Woo1
1Department of Chemistry , University of Ulsan , 93 Daehak-Ro , Nam-Gu, Ulsan 44610 , Korea.
Abstract:
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.
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