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Relevant academic research and scientific papers

Zirconium and hafnium polyhedral oligosilsesquioxane complexes-green homogeneous catalysts in the formation of bio-derived ethers: Via a MPV/etherification reaction cascade

The polyhedral oligosilsesquioxane complexes, {[(isobutyl)7Si7O12]ZrOPri·(HOPri)}2 (I), {[(cyclohexyl)7Si7O12]ZrOPri·(HOPri)}2 (II), {[(isobutyl)7Si7O12]HfOPri·(HOPri)}2 (III) and {[(cyclohexyl)7Si7O12]HfOPri·(HOPri)}2 (IV), were synthesized in good yields from the reactions of M(OPri)4 (M = Zr, Hf) with R-POSS(OH)3 (R = isobutyl, cyclohexyl), resp. I-IV were characterized by 1H, 13C and 29Si NMR spectroscopy and their dimeric solid-state structures were confirmed by X-ray analysis. I-IV catalyze the reductive etherification of 2-hydroxy- and 4-hydroxy and 2-methoxy and 4-methoxybenzaldehyde and vanillin to their respective isopropyl ethers in isopropanol as a "green"solvent and reagent. I-IV are durable and robust homogeneous catalysts operating at temperatures of 100-160 °C for days without significant loss of catalytic activity. Likewise, I-IV selectively catalyze the conversion of 5-hydroxymethylfurfural (HMF) into 2,5-bis(isopropoxymethyl)furane (BPMF), a potentially high-performance fuel additive. Similar results were achieved by using a combination of M(OPri)4 and ligand R-POSS(OH)3 as a catalyst system demonstrating the potential of this "in situ"approach for applications in biomass transformations. A tentative reaction mechanism for the reductive etherification of aldehydes catalysed by I-IV is proposed. This journal is

Uranyl(VI) Triflate as Catalyst for the Meerwein-Ponndorf-Verley Reaction

Catalytic transformation of oxygenated compounds is challenging in f-element chemistry due to the high oxophilicity of the f-block metals. We report here the first Meerwein-Ponndorf-Verley (MPV) reduction of carbonyl substrates with uranium-based catalysts, in particular from a series of uranyl(VI) compounds where [UO2(OTf)2] (1) displays the greatest efficiency (OTf = trifluoromethanesulfonate). [UO2(OTf)2] reduces a series of aromatic and aliphatic aldehydes and ketones into their corresponding alcohols with moderate to excellent yields, using iPrOH as a solvent and a reductant. The reaction proceeds under mild conditions (80 °C) with an optimized catalytic charge of 2.3 mol % and KOiPr as a cocatalyst. The reduction of aldehydes (1-10 h) is faster than that of ketones (>15 h). NMR investigations clearly evidence the formation of hemiacetal intermediates with aldehydes, while they are not formed with ketones.

Auto-Tandem Catalysis with Frustrated Lewis Pairs for Reductive Etherification of Aldehydes and Ketones

Herein we report that a single frustrated Lewis pair (FLP) catalyst can promote the reductive etherification of aldehydes and ketones. The reaction does not require an exogenous acid catalyst, but the combined action of FLP on H2, R-OH or H2O generates the required Br?nsted acid in a reversible, “turn on” manner. The method is not only a complementary metal-free reductive etherification, but also a niche procedure for ethers that would be either synthetically inconvenient or even intractable to access by alternative synthetic protocols.

Iodine-catalyzed transformation of aryl-substituted alcohols under solvent-free and highly concentrated reaction conditions

Iodine-catalyzed transformations of alcohols under solvent-free reaction conditions (SFRC) and under highly concentrated reaction conditions (HCRC) in the presence of various solvents were studied in order to gain insight into the behavior of the reaction intermediates under these conditions. Dimerization, dehydration and substitution were the three types of transformations observed with benzylic alcohols. Dimerization and substitution reactions were predominant in the case of primary- and secondary alcohols, whereas dehydration prevailed in the case of tertiary alcohols. The relative reactivity of substituted 1-phenylethanols in I2-catalyzed dimerization under SFRC provided a good Hammett plot ρ+ = -2.8 (r2 = 0.98), suggesting the presence of electron-deficient intermediates with a certain degree of developed charge in the rate-determining step.

A synthetic method of the compound animal pen ether class

The invention relates to a synthetic method of a benzyl ether compound. The synthetic method is used for avoiding environmental pollution caused by conventional benzyl ether compound synthetic methods. The synthetic method comprises following steps: step 1, a benzyl silane compound, an oxidizing agent, and a light reaction catalyst are delivered into a reactor, the reactor is vacuumized, and is filled with nitrogen for protection, an alkali compound and an alcohol reagent are delivered into the reactor through syringes, the reactor is exposed to visible light, reaction is carried out at room temperature with magnetic stirring, after reaction, an obtained reaction solution is filtered, and a liquid obtained via filtration is subjected to condensation so as to remove solvents and obtain a concentrated solution; and step 2, the concentrated solution is subjected to silica-gel column chromatography for separation and purification so as to obtain the benzyl ether compound, wherein a mixed solution of petroleum ether and ethyl acetate is taken as an eluent. Reaction conditions are mild; operation is simple and convenient; reaction yield is high; and the maximum reaction yield can be 93%.

Direct synthesis of ethers from aldehydes and ketones. One-pot reductive etherification of benzaldehydes, alkyl aryl ketones, and benzophenones

Benzyl alcohols formed by the reduction of benzaldehydes, alkyl aryl ketones, and benzophenones with sodium tetrahydridoborate in alcohols undergo in situ etherification with the solvent in the presence of a catalytic amount of HCl. Thus the process may be regarded as one-pot transformation of carbonyl compounds into the corresponding benzyl ethers. The yields of ethers depend on the substituent nature in the aromatic fragment of the initial carbonyl compound and on the alcohol used as reduction medium.

Sulfated tungstate as hydroxyl group activator for preparation of benzyl, including p-methoxybenzyl ethers of alcohols and phenols

Sulfated tungstate was found to be an effective heterogeneous and reusable catalyst for hydroxy group activation–mediated preparation of benzylic ethers including p-methoxybenzylic ethers of a wide range of alcohols and phenols under mild reaction conditions.

Chemoselective formation of unsymmetrically substituted ethers from catalytic reductive coupling of aldehydes and ketones with alcohols in aqueous solution

A well-defined cationic Ru-H complex catalyzes reductive etherification of aldehydes and ketones with alcohols. The catalytic method employs environmentally benign water as the solvent and cheaply available molecular hydrogen as the reducing agent to afford unsymmetrical ethers in a highly chemoselective manner.

Proton-exchanged montmorillonite-mediated reactions of methoxybenzyl esters and ethers

Proton-exchanged montmorillonite (H-mont) was found to be an eco-friendly and cost-effective catalyst for the generation of O-methylated quinone methides (QM) from the corresponding p or o-methoxybenzyl esters and ethers. Nucleophilic trapping of the O-methylated QM with arenes, alcohols, 1,3-dicarbonyl compounds, silyl enol ethers, and allylsilanes has been carried out, respectively, leading to eco-friendly benzylation reactions. Using this protocol, H-mont-mediated deprotection of PMB-protected esters and ethers have been realized for the first time. This work would pave the way for further exploration in O-alkylated QM that are of chemical and biological significance.

A very practical and selective method for PMB protection of alcohols

A very simple, practical and efficient one-step heterogeneous protocol for the PMB protection of alcohols using Amberlyst-15 has been developed. The stability and hazard issues regarding PMBCl and PMBBr are totally avoided by directly using anisyl alcohol for the protection. Alcohols are protected in very good yields. The selective mono-PMB protection of diols as well as di-PMB protection of diols was achieved in good yields, along with the demonstration of recyclability of the catalyst.