141-27-5Relevant academic research and scientific papers
Oxidation by Chemical Manganese Dioxide. Part 3.1 Oxidation of Benzylic and Allylic Alcohols, Hydroxyarenes and Aminoarenes
Hirano, Masao,Yakabe, Sigetaka,Chikamori, Hideki,Clark, James H.,Morimoto, Takashi
, p. 770 - 771 (1998)
The combined use of chemical manganese dioxide (CMD) and molecular sieves in hexane (or in acetone) in general or CMD alone in particular cases enables the convenient and efficient oxidation of benzylic and allylic alcohols, phenols and amines under relatively mild conditions.
Total Synthesis of (-)-Phorbaketal A
Joung, Seewon,Kim, Rira,Lee, Hee-Yoon
, p. 3903 - 3906 (2017)
A convergent asymmetric total synthesis of phorbaketal A was achieved in 10 steps through a Au(I)-catalyzed intramolecular spiroketalization reaction of an alkyne diol intermediate prepared from (R)-carvone and geranial. The spiroketalization reaction was
3,5-dimethylpyrazolium fluorochromate(VI)-catalysed oxidation of organic substrates by hydrogen peroxide under solvent-free conditions
Chaudhuri, Mihir K.,Dehury, Sanjay K.,Hussain, Sahid,Duarah, Ankur,Gogoi, Nayanmoni,Lakshmi Kantam
, p. 1349 - 1352 (2005)
3,5-Dimethylpyrazolium fluorochromate (VI), C5H 8N2H[CrO3F], DmpzHFC, serves as an efficient catalyst for oxidation of primary, secondary and allylic alcohols to the corresponding carbonyl compounds using H2O2 at room temperature under solvent-free conditions. Oxidation of methyl phenyl sulfides and triphenylphosphine were also carried out successfully.
Transition Metal-Substituted Potassium Silicotungstate Salts as Catalysts for Oxidation of Terpene Alcohols with Hydrogen Peroxide
da Silva, Marcio Jose,da Silva Andrade, Pedro Henrique,Sampaio, Vinicius Fernando Coelho
, p. 2094 - 2106 (2021)
Abstract: In this work, the catalytic activity of the transition metal-substituted potassium silicotungstate salts (i.e. K8-nSiMn+W11O39 (Mn+ = Cu2+, Co2+, Ni2+, Zn2+ and Fe3+) was investigated on the oxidation reactions of the terpene alcohols with H2O2 aqueous solution. The metal-substituted silicotungstate salts were easily synthesized in one-pot reactions of the precursor metal solutions (i.e. Na2WO4, Na2SiO3 and MCln) with KCl added in stoichiometric amount; after this precipitation step, the solid heteropoly salts were filtered and dried in an oven. This procedure of synthesis avoids multi-step processes that starts from the pristine heteropolyacid. The substituted metal heteropoly salts were characterized by infrared spectroscopy, measurements of the specific surface area (BET) and porosimetry by isotherms of adsorption/desorption of N2, X-rays diffraction, thermal analyses, dispersive X-rays spectroscopy, scanning electronic microscopy. The acidity strength was estimated by potentiometric titration with n-butylamine. All the salts were evaluated as catalysts in terpenic alcohols oxidation reactions with H2O2. The K5SiFeW11O39 was the most active and selective catalyst toward oxidation products. The impacts of the main reaction variables such as catalyst concentration, temperature, oxidant load, and nature of the terpene substrate were assessed. The highest activity of the K5SiFeW11O39 catalyst was assigned to the highest Lewis acidity. Graphic Abstract: [Figure not available: see fulltext.].
Asymmetric total synthesis of ieodomycin B
Lin, Shuangjie,Zhang, Jianting,Zhang, Zhibin,Xu, Tianxiang,Huang, Shuangping,Wang, Xiaoji
, (2017)
Ieodomycin B, which shows in vitro antimicrobial activity, was isolated from a marine Bacillus species. A novel asymmetric total synthetic approach to ieodomycin B using commercially available geraniol was achieved. The approach involves the generation of 1,3-trans-dihydroxyl at C-3 and C-5 positions via a Crimmins-modified Evans aldol reaction and a chelation-controlled Mukaiyama aldol reaction of a p-methoxybenzyl-protected aldehyde, as well as the generation of a lactone ring in a deprotection-lactonization one-pot reaction.
Remarkable substituent effects on the oxidizing ability of triarylbismuth dichlorides in alcohol oxidation
Matano, Yoshihiro,Hisanaga, Teppei,Yamada, Hisatsugu,Kusakabe, Shingo,Nomura, Hazumi,Imahori, Hiroshi
, p. 8676 - 8680 (2004)
Substituent effects on the oxidizing ability of triarylbismuth dichlorides were examined by intermolecular and intramolecular competition experiments on geraniol oxidation in the presence of DBU. It was found that the oxidizing ability of the dichlorides increases with increasing electron-withdrawing ability of the para substituents, and by introduction of a methyl group at the ortho position of the aryl ligands attached to the bismuth. The intermolecular and intramolecular H/D kinetic isotope effects observed for the competitive oxidation of p-bromobenzyl alcohols indicate that the rate-determining step involves C-H bond cleavage. Several primary and secondary alcohols were oxidized efficiently under mild conditions by the combined use of newly developed organobismuth(V) oxidants and DBU.
Highly efficient aerobic oxidation of benzylic and allylic alcohols by a simple catalyst system of [RuCl2(p-cymene)]2/Cs2CO3
Lee,Chang
, p. 7507 - 7510 (2000)
A new catalyst system of [RuCl2(p-cymene)]2/Cs2CO3 has been disclosed for highly efficient aerobic oxidation of activated alcohols to the corresponding carbonyl compounds, which is characterized by its high selectivity and activity, operational simplicity, and low air and moisture sensitivity. (C) 2000 Elsevier Science Ltd.
POLYMER-ANCHORED VANADIUM(V) AND MOLYBDENUM(VI) CATALYSTS FOR THE REGIOSELECTIVE EPOXIDATION OF (E)-GERANIOL WITH t-BUTYL HYDROPEROXIDE
Yokoyama, Toshiro,Nishizawa, Masato,Kimura, Tetsuo,Suzuki, Toshishige M.
, p. 1703 - 1706 (1983)
The reaction of (E)-geraniol with t-BuOOH in the presence of polymer-anchored VV or MoVI complexes gave 2,3-epoxygeraniol in high yields.The conversion and the selectivity by the MR-type polymer catalysts containing VV were comparable to those given by homogeneous catalyst based on VO(acac)2.The present catalysts can be used repeatedly without causing significant decrease in catalytic activity.
Saegusa Oxidation of Enol Ethers at Extremely Low Pd-Catalyst Loadings under Ligand-free and Aqueous Conditions: Insight into the Pd(II)/Cu(II)-Catalyst System
Zhu, Quan,Luo, Yunsong,Guo, Yongyan,Zhang, Yushun,Tao, Yunhai
, p. 5463 - 5476 (2021/05/05)
A highly efficient and practical Pd(II)/Cu(OAc)2-catalyst system of Saegusa oxidation, which converts enol ethers to the corresponding enals with a number of diverse substrates at extremely low catalyst loadings (500 mol ppm) under ligand-free and aqueous conditions, is described. Its synthetic utility was demonstrated by large-scale applications of the catalyst system to important nature molecules. This work allows Saegusa oxidation to become a highly practical approach to preparing enals and also suggests new insight into the Pd(II)/Cu(II)-catalyst system for dehydrogenation of carbonyl compounds and decreasing Pd-catalyst loadings.
Method for preparing olefine aldehyde through catalytic oxidation of enol ether
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Paragraph 0082-0086; 0089, (2021/06/23)
The invention relates to the technical field of olefine aldehyde preparation, and provides a method for preparing olefine aldehyde through catalytic oxidation of enol ether. According to the invention, a palladium catalyst, a copper salt, a solvent and enol ether are mixed and subjected to a catalytic oxidation reaction to obtain olefine aldehyde. According to the method, the copper salt is used as the oxidizing agent, the mixed solvent of water and acetonitrile is used as the reaction solvent, and the volume ratio of water to acetonitrile in the mixed solvent is controlled to be (3-7): (3-7), so that the catalytic oxidation reaction can be smoothly carried out in the mixed solvent with a specific ratio, and the generation of palladium black precipitate can be avoided. The method provided by the invention has the advantages of simple steps, low reagent cost, no need of dangerous reagents, wide substrate adaptability and small catalyst dosage. Furthermore, octadecane mercaptan is added to promote the catalytic oxidation reaction, and when the dosage of the palladium catalyst is extremely low, the olefine aldehyde yield can be greatly increased by adding octadecane mercaptan.
