1187667-17-9Relevant 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.
Silver(I)-Catalyzed deprotection of p -methoxybenzyl ethers: A mild and chemoselective method
Kern, Nicolas,Dombray, Thomas,Blanc, Aurelien,Weibel, Jean-Marc,Pale, Patrick
, p. 9227 - 9235,9 (2012/12/12)
The p-methoxybenzyl protecting group (PMB) on various alcohols and an acid was efficiently and selectively cleaved by the action of a catalytic amount of silver(I) hexafluoroantimonate combined with 0.5 equiv of 1,3,5- trimethoxybenzene in dichloromethane at 40 °C.
Oxidative photoredox catalysis: Mild and selective deprotection of PMB ethers mediated by visible light
Tucker, Joseph W.,Narayanam, Jagan M. R.,Shah, Pinkey S.,Stephenson, Corey R. J.
supporting information; experimental part, p. 5040 - 5042 (2011/06/10)
Herein we report an advancement in the application of visible light photoredox catalysts in the oxidation of electron-rich arenes resulting in the selective deprotection of para-methoxybenzyl (PMB) ethers. This method is highlighted by excellent functional group tolerance, protecting group orthogonality, mild reaction conditions and avoidance of stoichiometric redox byproducts.
A mild method for the protection of alcohols using a para-methoxybenzylthio tetrazole (PMB-ST) under dual acid-base activation
Kotturi, Santosh R.,Tan, Jason S.,Lear, Martin J.
supporting information; experimental part, p. 5267 - 5269 (2009/12/24)
With a view to expand the repertoire of chemoselective methods applicable to sensitive and multifunctional substrates, the p-methoxybenzylation of alcohols under essentially neutral conditions is reported. This was achieved by the silver triflate (AgOTf) activation of 5-(p-methoxybenzylthio)-1-phenyl-1H-tetrazole (PMB-ST) in the presence of 2,6-di-tert-butyl-4-methylpyridine (DTBMP).
