736109-58-3Relevant academic research and scientific papers
Chemoselective Electrochemical Oxidation of Secondary Alcohols Using a Recyclable Chloride-Based Mediator
Sommer, Florian,Kappe, C. Oliver,Cantillo, David
supporting information, p. 166 - 170 (2021/06/16)
Selective anodic oxidation of alcohols in the presence of other functional groups can be accomplished by using nitroxyl radical mediators. However, the electrochemical chemoselective oxidation of secondary alcohols in the presence of primary alcohols is a
A Convenient Protocol for the Oxidation of Benzyl and Secondary Alcohols to Carbonyl Compounds by Trichoroisocyanuric Acid
De Mattos, Marcio C. S.,Dos Santos, Carlos Vinicius P.
, p. 854 - 861 (2022/03/01)
A very convenient methodology to oxidize benzyl alcohols to benzaldehydes (9 examples, up to 95%) and secondary alcohols to ketones (8 examples, up to 99%) using trichloroisocyanuric acid in CH2Cl2/MeCN (1:1) as co-solvent in the presence of water at room temperature is presented in this study.
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 (2020/11/13)
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.].
Photochemical oxidation of benzylic primary and secondary alcohols utilizing air as the oxidant
Nikitas, Nikolaos F.,Tzaras, Dimitrios Ioannis,Triandafillidi, Ierasia,Kokotos, Christoforos G.
supporting information, p. 471 - 477 (2020/02/13)
A mild and green photochemical protocol for the oxidation of alcohols to aldehydes and ketones was developed. Utilizing thioxanthenone as the photocatalyst, molecular oxygen from air as the oxidant and cheap household lamps or sunlight as the light source, a variety of primary and secondary alcohols were converted into the corresponding aldehydes or ketones in low to excellent yields. The reaction mechanism was extensively studied.
Direct Oxidation of Csp3?H bonds using in Situ Generated Trifluoromethylated Dioxirane in Flow
Lesieur, Mathieu,Battilocchio, Claudio,Labes, Ricardo,Jacq, Jér?me,Genicot, Christophe,Ley, Steven V.,Pasau, Patrick
supporting information, p. 1203 - 1207 (2019/01/04)
A fast, scalable, and safer Csp3?H oxidation of activated and un-activated aliphatic chains can be enabled by methyl(trifluoromethyl)dioxirane (TFDO). The continuous flow platform allows the in situ generation of TFDO gas and its rapid reactivity toward tertiary and benzylic Csp3?H bonds. The process exhibits a broad scope and good functional group compatibility (28 examples, 8–99 %). The scalability of this methodology is demonstrated on 2.5 g scale oxidation of adamantane.
Solventless, selective and catalytic oxidation of primary, secondary and benzylic alcohols by a Merrifield resin supported molybdenum(vi) complex with H2O2 as an oxidant
Boruah, Jeena Jyoti,Das, Siva Prasad
, p. 34491 - 34504 (2018/10/21)
Here, we have described the synthesis, characterization and catalytic activity of a dioxo-molybdenum(vi) complex supported on functionalized Merrifield resin (MR-SB-Mo). The functionalization of Merrifield resin (MR) was achieved in two-steps viz. carbonylation (MR-C) and Schiff base formation (MR-SB). The compounds, MR-C, MR-SB and MR-SB-Mo, were characterized at each step of the synthesis by elemental, SEM, EDX, thermal, BET and different spectroscopic analysis. The catalyst, MR-SB-Mo, efficiently and selectively oxidized a wide variety of alcohols to aldehydes or ketones using 30% H2O2 as an oxidant with reasonably good TOF (660 h-1 in case of benzyl alcohol). The catalyst acted heterogeneously under solventless reaction conditions and did not lead to over oxidized products under optimized conditions. The catalyst afforded regeneration and can be reused for at least five reaction cycles without loss of efficiency and product selectivity. A reaction mechanism for the catalytic activity of MR-SB-Mo was proposed and a probable reactive intermediate species isolated.
Revisiting Sodium Hypochlorite Pentahydrate (NaOCl·5H 2 O) for the Oxidation of Alcohols in Acetonitrile without Nitroxyl Radicals
Hirashita, Tsunehisa,Sugihara, Yuto,Ishikawa, Shota,Naito, Yohei,Matsukawa, Yuta,Araki, Shuki
, p. 2404 - 2407 (2018/11/23)
Sodium hypochlorite pentahydrate (NaOCl·5H 2 O) is capable of oxidizing alcohols in acetonitrile at 20 °C without the use of catalysts. The oxidation is selective to allylic, benzylic, and secondary alcohols. Aliphatic primary alcohols are not oxidized.
METHOD FOR PRODUCING CARBONYL COMPOUND
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Paragraph 0032-0035; 0037-0040, (2018/03/23)
PROBLEM TO BE SOLVED: To provide a method for producing a carbonyl compound, allowing for improvement of ease of production and furthermore allowing for reduction of production cost, by positively utilizing inexpensive iodine. SOLUTION: A carbonyl compound is produced by mixing primary alcohol or secondary alcohol, and iodic acid (HIO3) in a non-solvent or an aprotic polar solvent based on the following general formula (1), where R1 is an optionally substituted linear- or branched 1-12C aliphatic group, or an optionally substituted aromatic group; R2 is a hydrogen atom, an optionally substituted linear- or branched 1-12C alkyl group, or an optionally substituted aromatic group; R1 and R2 each may be coupled with each other to form a ring of aromatic group or a non-aromatic group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
Polyethylene Glycols as Efficient Catalysts for the Oxidation of Bicyclic Monoterpenes by Ceric Ammonium Nitrate in Acetonitrile under Acid-Free Conditions: Kinetic and Mechanistic Approach
Rajitha,Shylaja,Rajanna,Yadagiri
, p. 383 - 396 (2018/03/30)
Polyethylene glycols (PEG) acts as efficient catalysts for the oxidation of bicyclic monoterpenes such as borneol, isoborneol, and camphor by ceric ammonium nitrate (CAN), a laboratory desktop reagent, in acetonitrile medium under mineral acid-free conditions. The kinetics of the reactions revealed first-order dependence on in both [CAN] and [bicyclic terpene]. The rate of oxidation is accelerated with an increase in [PEG] linearly, which could be explained by considering PEG-bound oxidant (PEG-CAN) as more reactive species than (CAN) itself. The mechanism of oxidation in PEG media has been explained through the participation of PEG-bound oxidant (PEG-CAN) and bicyclic monoterpene in the slow step.
A TEMPO-like nitroxide combined with an alkyl-substituted pyridine: An efficient catalytic system for the selective oxidation of alcohols with iodine
Kashparova, Vera P.,Klushin, Victor A.,Zhukova, Irina Yu.,Kashparov, Igor S.,Chernysheva, Daria V.,Il'chibaeva, Irina B.,Smirnova, Nina V.,Kagan, Efim Sh.,Chernyshev, Victor M.
supporting information, p. 3517 - 3521 (2017/10/05)
An efficient method for the oxidation of alcohols to aldehydes or ketones in a two-phase CH2Cl2/NaHCO3 (aq.) system, using iodine and catalytic amounts of 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxyl and 2,4,6-trimethylpyridine, was developed. The performance of the method was demonstrated by the selective oxidation of 37 variously substituted alcohols in ≥90% yield, including the gram-scale synthesis of the important chemical 2,5-diformylfuran from biomass-derived 5-hydroxylmethylfurfural.
