2206-38-4Relevant academic research and scientific papers
Copper(II)-catalyzed O-phenylation of alcohols with organobismuth(V) reagents: A convenient method for the synthesis of simple tert-alkyl phenyl ethers
Mukaiyama, Teruaki,Sakurai, Naoto,Ikegai, Kazuhiro
, p. 1140 - 1141 (2006)
A convenient method for copper(II)-catalyzed O-phenylation of simple alcohols with organobismuth(V) compounds under mild conditions is described. Treatment of tetraphenylbismuth fluoride (Ph4BiF) with various simple alcohols in the presence of
Synthesis of orderly nanoporous aluminophosphate and zirconium phosphate materials and their catalytic applications
Sreenivasulu, Peta,Viswanadham, Nagabhatla,Sharma, Trymbkesh,Sreedhar
, p. 6232 - 6235 (2014)
Amorphous alumino phosphate (AP) and zirconium phosphate (ZP) materials possessing an ordered nanoporosity have been successfully synthesized by a hydrothermal method using a P123 block co-polymer as the structure directing agent. The materials exhibited excellent catalytic activity towards selective alkylation of phenol with cyclohexanol, where AP showed as high as 100% selectivity to produce the industrially important O-alkylation product, while the corresponding ZP selectively produced a C-alkylation product (93% selectivity). This journal is the Partner Organisations 2014.
Rational synthesis of palladium nanoparticles modified by phosphorous for the conversion of diphenyl ether to KA oil
Bai, Hong-Cun,Cao, Jing-Pei,Jiang, Wei,Wei, Yu-Lei,Xie, Jin-Xuan,Zhang, Chuang,Zhao, Liang,Zhao, Ming,Zhao, Xiao-Yan
, (2021/12/23)
Conversion of lignin-derived molecules into value-added chemicals is critical for sustainable chemistry but still challenging. Herein, phosphorus-modified palladium catalyzed the degradation of lignin-derived 4-O-5 linkage to produce KA oil (cyclohexanone-cyclohexanol oil) was reported. The reaction proceeds via a restricted partial hydrogenation-hydrolysis pathway. Phosphorus-modified palladium catalyst suppressed the full hydrogenation of diary ether, which was the key point to produce KA oil selectively. Under the optimized conditions, the 4.5 nm Pd-P NPs could catalyze the conversion of 4-O-5 linkage into KA oil in 83% selectivity with a high production rate of 32.5 mmol·g?1Pd·min?1. This study represented an original method for KA oil production.
Rh-PVP Catalyzed Reductive Amination of Phenols by Ammonia or Amines to Cyclohexylamines under Solvent-free Conditions
Chaudhari, Chandan,Nagaoka, Katsutoshi,Nishida, Yoshihide,Rumi, Saeki,Sato, Katsutoshi,Shiraishi, Masaya
supporting information, p. 81 - 84 (2022/01/12)
Colloidal metal nanoparticles were examined for reductive amination of phenol by ammonia under mild reaction conditions. The results showed that Rh-PVP was the most active catalyst for reductive amination reaction. Linear, cyclic, and amino alcohols were used as nucleophiles and converted to primary/secondary/tertiary amines. Using this strategy, the synthesis of an industrially important chemical, N-cyclohexyl- 2-pyrrolidone was explored.
Hydrodeoxygenation of Lignin-Derived Aromatic Oxygenates Over Pd-Fe Bimetallic Catalyst: A Mechanistic Study of Direct C–O Bond Cleavage and Direct Ring Hydrogenation
Zhang, Jianghao,Sudduth, Berlin,Sun, Junming,Wang, Yong
, p. 932 - 939 (2020/09/02)
Hydrodeoxygenation of lignin-derived phenols could be achieved generally with three reaction pathways: tautomerization, direct ring hydrogenation and direct C–O bond cleavage. The former pathway has been extensively studied over Pd/Fe catalyst in liquid-phase reaction, however, the contribution of the latter two is yet subject to further investigations. In this report, a comparative study of direct C–O bond cleavage and direct ring hydrogenation reaction pathways is presented on Pd/Fe, Fe and Pd/C catalysts using diphenyl ether as modelling compound. Despite its much higher activation energy than direct ring hydrogenation, direct C–O bond cleavage is dominant over Pd/Fe with much higher rates than the monometallic analogues due to the synergic catalysis of Pd–Fe. Based on this study and our previous results, the detailed reaction network for HDO of diphenyl ether is proposed. Graphic Abstract: [Figure not available: see fulltext.]
Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols
Bai, Jixiang,Wang, Tianxin,Dai, Botao,Liu, Qingchao,Yu, Peiyuan,Jia, Tiezheng
supporting information, p. 5761 - 5765 (2021/08/16)
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Hydrogenolysis of aromatic ethers under lignin-first conditions
Beneduci, A.,Corrente, G. A.,Malara, A.,Mauriello, F.,Paone, E.
, (2020/10/14)
The cleavage of the etheric C–O bond in diphenyl ether (DPE), phenethyl phenyl ether (PPE) and benzyl-phenyl ether (BPE) has been investigated by using Ru/C (5% wt) and Pd/C (5% wt), as heterogeneous catalysts, under reaction conditions generally adopted for the reductive catalytic fractionalization of lignocellulosic biomasses (lignin-first approach). Catalytic tests were carried out in the presence of simple C1-C3 alcoholic H-donor solvents (methanol, ethanol and 2-propanol) used as such or in mixture with water in the temperature range of 120–240 °C both in the presence or in the absence of molecular hydrogen as reducing agent. Under transfer hydrogenolysis conditions, the Ru/C catalyst was found to be the best performing system in the cleavage of the 4–O–5 etheric C–O bond (95 % DPE conversion in 2-propanol at 210 °C after 3 h of reaction) with a less pronounced tendency in hydrogenating the aromatic ring. Upon increasing the water content in the reaction medium, a decrease in the cleavage of the C–O bond of DPE together with a higher production of phenolics is observed as a consequence of the reductive hydrolysis reaction occurrence. The best yield in aromatic compounds (52 %) was obtained by using as solvent a water/2-propanol (75:25, v/v) mixture in absence of added molecular hydrogen, with the alcoholic fraction being the in-situ H-source. A lower tendency to undergo to hydrolysis reaction together with a higher production of aromatics is registered in the case of phenethyl phenyl ether and benzyl-phenyl ether. Results are explained in terms of the higher steric hindrance of PPE and BPE with respect to DPE and of the competitive adsorption of arenes arising from hydrogenolysis of etheric β–O–4 and α–O–4 bonds (phenol + ethyl benzene or phenol + toluene) on the Ru/C catalyst surface.
Liquid-phase hydrodeoxygenation of lignin-derived phenolics on Pd/Fe: A mechanistic study
Zhang, Jianghao,Sun, Junming,Sudduth, Berlin,Pereira Hernandez, Xavier,Wang, Yong
, p. 305 - 311 (2019/01/04)
Although Pd/Fe bimetallic catalysts have been extensively studied in vapor-phase hydrodeoxygenation of phenolics (i.e., guaiacol, cresol), little is yet known about their performance in liquid-phase reactions. In this work, we present a mechanistic study on the Pd/Fe bimetallic catalysts in liquid-phase hydrodeoxygenation of phenolics. The role of tautomerization in hydrodeoxygenation of the lignin-derived phenolics, particularly for ring saturation, is systematically studied by employing two representative modeling compounds: phenol (a molecule that is keto-enol tautomeric) and diphenyl ether (a molecule that does not allow ketol-enol tautomerization). It was found that although the addition of oxyphilic Fe inhibits the direct aromatic ring saturation reaction typically occurring on Pd, tautomerization opens another reaction pathway toward ring saturation products (i.e. cyclohexanone, cyclohexanol, cyclohexane et al.), where both tautomerization and the hydrogenation of keto isomers are significantly enhanced to produce cyclohexanol followed by direct hydrogenolysis of the cyclohexanol to cyclohexane.
CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions
Mohammadinezhad, Arezou,Akhlaghinia, Batool
, p. 332 - 352 (2020/01/11)
Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].
Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
Ming, Xiao-Xia,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 3370 - 3379 (2019/11/03)
A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.
