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Photoredox Removal of p ‐Methoxybenzyl Ether Protecting Group with Hydrogen Peroxide as Terminal Oxidant
Author(s) -
Liu Zheng,
Zhang Yi,
Cai Zheren,
Sun Hao,
Cheng Xu
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400936
Subject(s) - chemistry , hydrogen peroxide , ether , eosin y , photoredox catalysis , primary (astronomy) , catalysis , protecting group , reactivity (psychology) , organic chemistry , combinatorial chemistry , photocatalysis , medicine , physics , alkyl , alternative medicine , pathology , astronomy
We report a mild protocol for removal of the p ‐methoxybenzyl ether protecting group under acidic conditions with eosin Y combined with LEDs as a photoredox catalysis system and hydrogen peroxide as the terminal oxidant. This protocol is compatible with ethers derived from primary, secondary, and tertiary alcohols, as well as with various functional groups. The protocol showed unusual selectivity for a tertiary ether over a primary ether. The scale up to gram scale is also explored and identical reactivity is observed.