1020186-15-5Relevant academic research and scientific papers
Oxidative Deprotection of p-Methoxybenzyl Ethers via Metal-Free Photoredox Catalysis
Ahn, Deok Kyun,Kang, Young Woo,Woo, Sang Kook
, p. 3612 - 3623 (2019/03/11)
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.
Photoredox removal of p-methoxybenzyl ether protecting group with hydrogen peroxide as terminal oxidant
Liu, Zheng,Zhang, Yi,Cai, Zheren,Sun, Hao,Cheng, Xu
supporting information, p. 589 - 593 (2015/03/05)
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.
A simple and an efficient indium trichloride catalyzed benzyl etherification
Bhaskar,Solomon,Babu,Muralidharan,Perumal, Paramasivan T.
scheme or table, p. 795 - 801 (2011/01/04)
An efficient method has been developed for the synthesis of benzyl ethers of alkyl, allyl and propargyl alchols by simple, direct coupling of alcohols in the presence of catalytic amount of L1C13 under solvent-free condition.
An efficient means for generating p-methoxybenzyl (PMB) ethers under mildly acidic conditions
Stewart, Catherine A.,Peng, Xiaowen,Paquette, Leo A.
, p. 433 - 437 (2008/09/20)
The protection of a wide variety of alcohols as their p-methoxybenzyl ethers can be performed with PMBO-lepidine in the presence of methyl tosylate or, preferably, camphorsulfonic acid. No inorganic promoters are required, thereby facilitating workup and product isolation. Georg Thieme Verlag Stuttgart.
