16224-09-2Relevant academic research and scientific papers
Selective hydrogenation of lignin-derived compounds under mild conditions
Chen, Lu,Van Muyden, Antoine P.,Cui, Xinjiang,Laurenczy, Gabor,Dyson, Paul J.
supporting information, p. 3069 - 3073 (2020/06/17)
A key challenge in the production of lignin-derived chemicals is to reduce the energy intensive processes used in their production. Here, we show that well-defined Rh nanoparticles dispersed in sub-micrometer size carbon hollow spheres, are able to hydrogenate lignin derived products under mild conditions (30 °C, 5 bar H2), in water. The optimum catalyst exhibits excellent selectivity and activity in the conversion of phenol to cyclohexanol and other related substrates including aryl ethers.
Reductive Etherification of Aldehydes and Ketones with Alcohols and Triethylsilane Catalysed by Yb(OTf)3: an Efficient One-Pot Benzylation of Alcohols
Pelosi, Azzurra,Lanari, Daniela,Temperini, Andrea,Curini, Massimo,Rosati, Ornelio
supporting information, p. 4527 - 4539 (2019/08/26)
The one-pot synthesis of symmetrical and unsymmetrical ethers from aldehydes and ketones can be conveniently performed using Yb(OTf)3 as catalyst and triethylsilane as reducing agent in presence of alcohols. This methodology leads to the synthesis of ether derivatives with good yields. Notably, this process resulted a useful tool to protect alcohols as benzyl ether derivatives using differently substituted benzaldehydes as protecting agents under mild conditions. A plausible mechanism was also proposed. (Figure presented.).
Entrapment of THF-Stabilized Iridacyclic IrIII Silylenes from Double H?Si Bond Activation and H2 Elimination
Binh, Dang Ho,Hamdaoui, Mustapha,Fischer-Krauser, Diane,Karmazin, Lydia,Bailly, Corinne,Djukic, Jean-Pierre
supporting information, p. 17577 - 17589 (2018/11/23)
The reaction of H3SiR (R=Ph, nBu) with cationic η5-C5Me5- (Cp*) and benzo[h]quinolinyl-based iridacycle [1 b]+ gives rise to new [(IrH)→SiRH2]+ adducts. In the presence of THF these adducts readily undergo elimination of H2 gas at subambient temperature to form THF-stabilized metallacyclic IrIII silylene complexes, which were characterized in situ by NMR spectroscopy, trapped in minute amounts by reactive crystallization, and structurally characterized by XRD. Theoretical investigations (static DFT-D reaction-energy profiling, ETS-NOCV) support the promoting role of THF in the H2 elimination step and the consolidation of the Ir-to-Si interaction in the spontaneous (ΔG+/phenylsilane system are relevant catalytic species in the hydrodefluorination of fluoroalkanes.
Synthesis of Benzyl Alkyl Ethers by Intermolecular Dehydration of Benzyl Alcohol with Aliphatic Alcohols under the Effect of Copper Containing Catalysts
Bayguzina,Gimaletdinova,Khusnutdinov
, p. 1148 - 1155 (2018/10/24)
Synthesis of benzyl alkyl ethers was performed in high yields by intermolecular dehydration of benzyl and primary, secondary, tertiary alcohols under the effect of copper containing catalysts. The formation of benzyl alkyl ethers occurs with participation of benzyl cation.
Palladium on Carbon-Catalyzed Benzylic Methoxylation for Synthesis of Mixed Acetals and Orthoesters
Yasukawa, Naoki,Kanie, Takafumi,Kuwata, Marina,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 10974 - 10977 (2017/08/22)
The palladium on carbon (Pd/C)-catalyzed direct methoxylation of the benzylic positions of linear benzyl and cyclic ether substrates proceeded in the presence of i-Pr2NEt under an oxygen atmosphere to give the corresponding mixed acetals. Cyclic acetal derivatives could also be converted into orthoesters. The present direct methoxylation via a carbon-hydrogen (C?H) functionalization can be accomplished using the easily-removed Pd/C and molecular oxygen as a green oxidant. The obtained mixed acetals were transformed into the corresponding ether products by chemoselective substitution of the methoxy group using a silyltriflate, 2,4,6-collidine, and a nucleophile. The orthoester derivative could also be transformed into the cyclic ketal under similar reaction conditions.
Specific reactivity of 2,4,6-tri-tert-butylanilide anions and its application to benzylation reagent
Yamada, Tomoyuki,Tsukagoshi, Shiori,Kitagawa, Osamu
, p. 317 - 320 (2017/01/03)
The reaction of methyl iodide with an anilide anion prepared from 2,4,6-tri-tert-butylanilide and NaH in CH3CN gave N-methyl anilide (N-alkylation product) as a major product, while in the reaction of benzyl bromide with the anilide anion in DMF, O-benzyl imidate (O-alkylation product) was obtained with almost complete selectivity. The treatment of O-benzyl imidate with alcohols and carboxylic acids in the presence of trifluoromethane sulfonic acid gave benzyl ethers and benzyl esters, respectively.
Vanadium-Catalyzed Oxidative Debenzylation of O-Benzyl Ethers at ppm Level
Urgoitia, Garazi,SanMartin, Raul,Herrero, María Teresa,Domínguez, Esther
supporting information, p. 3307 - 3312 (2016/10/21)
An advantageous methodology for the oxidative debenzylation of ethers has been developed. Very low amounts of a catalyst system based on vanadyl acetylacetonate and a triazole type pincer ligand allow the selective oxidative cleavage of a number of O-benzyl ethers in the presence of oxygen as the sole oxidant. The methodology tolerates a number of functional groups such as halo-, alkoxy-, or trifluoromethylarenes, alkyne, alkene, ether, and acetal units. Large-scale deprotections can be also carried out by the optimized procedure, which is amenable to enantioenriched reactants as well. (Figure presented.).
A gold catalytic the method for synthesizing calls the ether
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Paragraph 0029-0032; 0034; 0036, (2017/02/28)
The invention provides a synthetic method of asymmetrical ether in the field of organic synthesis. The general equation of reaction is defined in the specification. In the equation, R-OH is benzyl alcohol, p-methoxy benzyl alcohol, tert-butyl alcohol, diphenyl carbinol or triphenylmethanol; and R'OH is common alkyl alcohol or a compound containing hydroxyl groups. A gold catalyst required by the reaction is Ph3PAuCl, Ph3PAuNTf2, HAuCl4, NaAuCl4, Ph3PAuOTf, Ph3PAuSbF6, IPrAuCl or nano-gold. A medium required by the reaction is solvent-free, and is toluene, mesitylene, 1,2-dichloroethane, tetrahydrofuran, acetonitrile or acetone. The reaction is implemented by heating through a microwave reactor. The method has advantages as follows: raw materials are easily available; operation is simple; the range of application is wide; atom economy is good; and the reaction is green.
Synthesis of ethers from carbonyl compounds by reductive etherification catalyzed by iron(III) and silyl chloride
Savela, Risto,Leino, Reko
, p. 1749 - 1760 (2015/06/16)
A simple iron- and silyl chloride catalyzed method for the preparation of symmetrical and nonsymmetrical ethers is presented. Various aldehydes and ketones were reductively etherified by using triethylsilane as a reducing agent in the presence of 2 mol% of iron(III) oxo acetate and 8 mol% of chloro(trimethyl)silane. The reactions can be carried out at ambient temperatures and pressures with ethyl acetate as the solvent.
Visible-light-promoted conversion of alkyl benzyl ether to alkyl ester or alcohol via O-α-sp3 C-H cleavage
Lu, Ping,Hou, Tianyuan,Gu, Xiangyong,Li, Pixu
supporting information, p. 1954 - 1957 (2015/04/27)
A mild and high-yielding visible-light-promoted conversion of alkyl benzyl ethers to the alkyl esters or alkyl alcohols was developed. Mechanistic studies provided evidence for a radical chain reaction involving the homolytic cleavage of O-α-sp3 C-H bonds in the substrate as one of the propagation steps. We propose that α-bromoethers are key intermediates in the transformation.
