104330-36-1Relevant articles and documents
A highly efficient and convenient method for the direct conversion of alkyl THP ethers into the corresponding alkyl benzyl ethers
Suzuki, Takeshi,Ohashi, Kousaburo,Oriyama, Takeshi
, p. 1561 - 1563 (1999)
Direct conversion of alcohol tetrahydropyranyl (THP) ethers into the corresponding benzyl ethers can be conveniently performed by reaction with triethylsilane and benzaldehyde in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfona
Synthesis of para-methoxybenzyl (PMB) ethers under neutral conditions
Nwoye, Ernest O.,Dudley, Gregory B.
, p. 1436 - 1437 (2007)
2-(4-Methoxybenzyloxy)-4-methylquinoline reacts with methyl triflate in the presence of alcohols to generate a neutral organic salt that transfers the para-methoxybenzyl (PMB) protecting group onto alcohols in high yield and under mild conditions. The Royal Society of Chemistry.
Development of a Storable Triazinone-Based Reagent for O- p-Methoxybenzylation under Mild Heating Conditions
Fujita, Hikaru,Terasaki, Hiromitsu,Kakuyama, Satoshi,Hioki, Kazuhito,Kunishima, Munetaka
, (2019)
A new triazinone-based reagent for O-p-methoxybenzylation has been developed. In spite of its stability in solid form, this reagent converts a free alcohol into the corresponding p-methoxybenzyl ether with mild heating (50-60 °C) in a solution. High funct
CONTROLLED OXIDATION OF BENZYL ETHERS ON IRRADIATED SEMICONDUCTOR POWDERS
Pincock, James A.,Pincock, Alexandra L.,Fox, Marye Anne
, p. 4107 - 4118 (1985)
Irradiation of a suspension of powdered TiO2, a photoactive semiconductor, in oxygen saturated acetonitrile leads to mild selective oxidation of substrates containing a benzylic methylene by conversion of that carbon to a carbonyl group.The method is shown to be synthetically useful for the preparation of esters from ethers and ketones from hydrocarbons.A critical analysis of the products and of the possible intermediates results in a plausible mechanistic pathway for these photooxidations.
p-Methylbenzyl 2,2,2-Trichloroacetimidate: Simple Preparation and Application to Alcohol Protection
Arai, Tomoki,Ikeuchi, Kazutada,Murasawa, Kentaro,Yamada, Hidetsohi
supporting information, p. 1034 - 1037 (2020/09/16)
A method for p-methylbenzyl (MBn) protection of alcohols by using MBn 2,2,2-trichloroacetimidate is described. The trichloroacetimidate can easily be prepared and isolated as a stable white powder without purification by silica gel chromatography. Catalytic use of zinc(II) triflate in diethyl ether activates the trichloroacetimidate to enable MBn protection of various alcohols.
Scalable Aerobic Oxidation of Alcohols Using Catalytic DDQ/HNO3
Arseniyadis, Stellios,Clavier, Louis,Copin, Chloé,Fournier, Jean,Giffard, Jean-Fran?ois,Jean, Alexandre,Katsina, Tania,Macedo Portela Da Silva, Nayane,Tamion, Rodolphe
supporting information, p. 856 - 860 (2020/07/14)
A selective, practical, and scalable aerobic oxidation of alcohols is described that uses catalytic amounts of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) and HNO3, with molecular oxygen serving as the terminal oxidant. The method was successfully applied to the oxidation of a wide range of benzylic, propargylic, and allylic alcohols, including two natural products, namely, carveol and podophyllotoxin. The conditions are also applicable to the selective oxidative deprotection of p-methoxybenzyl ethers.
Simple and rapid p-methoxybenzylation of hydroxy and amide groups at room temperature by NaOt-Bu and DMSO
Hamada, Shohei,Sugimoto, Koichi,Iida, Masashi,Furuta, Takumi
supporting information, (2019/11/13)
The p-methoxybenzylation of hydroxy and amide groups by p-methoxybenzyl chloride utilizing NaOt-Bu in DMSO is described. p-Methoxybenzylation of sterically hindered menthol using NaOt-Bu in DMSO proceeded faster than the commonly used methods which use Na
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.
Electrochemical Deprotection of para-Methoxybenzyl Ethers in a Flow Electrolysis Cell
Green, Robert A.,Jolley, Katherine E.,Al-Hadedi, Azzam A. M.,Pletcher, Derek,Harrowven, David C.,De Frutos, Oscar,Mateos, Carlos,Klauber, David J.,Rincón, Juan A.,Brown, Richard C. D.
, p. 2050 - 2053 (2017/04/27)
Electrochemical deprotection of p-methoxybenzyl (PMB) ethers was performed in an undivided electrochemical flow reactor in MeOH solution, leading to the unmasked alcohol and p-methoxybenzaldehyde dimethyl acetal as a byproduct. The electrochemical method removes the need for chemical oxidants, and added electrolyte (BF4NEt4) can be recovered and reused. The method was applied to 17 substrates with high conversions in a single pass, yields up to 92%, and up to 7.5 g h-1 productivity. The PMB protecting group was also selectively removed in the presence of some other common alcohol protecting groups.
Combining visible light catalysis and transfer hydrogenation for in situ efficient and selective semihydrogenation of alkynes under ambient conditions
Zhong, Jian-Ji,Liu, Qiang,Wu, Cheng-Juan,Meng, Qing-Yuan,Gao, Xue-Wang,Li, Zhi-Jun,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
supporting information, p. 1800 - 1803 (2016/02/05)
By combining visible light catalysis and transfer hydrogenation, we are able to convert a series of alkynes to their corresponding alkenes in high chemical yields. Then the visible light catalytic transfer hydrogenation reaction can couple photoisomerization to produce E-alkenes or Z-alkenes exclusively depending on the aryl or alkyl substituted alkynes.
