495-40-9Relevant articles and documents
Aqueous aerobic oxidation of alkyl arenes and alcohols catalyzed by copper(ii) phthalocyanine supported on three-dimensional nitrogen-doped graphene at room temperature
Mahyari, Mojtaba,Laeini, Mohammad Sadegh,Shaabani, Ahmad
, p. 7855 - 7857 (2014)
Copper(ii) tetrasulfophthalocyanine supported on three-dimensional nitrogen-doped graphene-based frameworks was synthesized and introduced as a bifunctional catalyst for selective aerobic oxidation of alkyl arenes and alcohols to the corresponding carbonyl compounds. The ease of catalyst separation, high turnover, low catalyst loading and recyclability could potentially render it applicable in industrial setting. This journal is the Partner Organisations 2014.
Gold nanoparticles supported on three-dimensional nitrogen-doped graphene: An efficient catalyst for selective aerobic oxidation of hydrocarbons under mild conditions
Mahyari, Mojtaba,Laeini, Mohammad Sadegh,Shaabani, Ahmad,Kazerooni, Hanif
, p. 456 - 461 (2015)
The development of efficient and selective aerobic oxidation of alkylarenes to form more functional compounds by heterogeneously catalysed routes still presents a great challenge in the fine chemical industry and is a major research topic. In this work, gold nanoparticles supported on three-dimensional nitrogen-doped graphene-based frameworks (Au NPs@3D-(N)GFs) were successfully synthesized and found to have an impressive performance as bifunctional catalysts (nitrogen dopant as base and gold nanoparticles as active site) in the controlled oxidation of alkylarenes. The catalyst was found to be a simple bench top, stable, recyclable and selective catalytic system for the aerobic oxidation of various types of alkylarenes into their corresponding ketones at room temperature under environmentally friendly conditions with good yields and high selectivity.
Reductive selenation of aliphatic ketones to dialkyl diselenides with Se-CO-H2O under atmospheric pressure
Chen, Yahong,Tian, Fengshou,Song, Maoping,Lu, Shiwei
, p. 1235 - 1237 (2008)
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Diastereoselective reductive aldol reaction of enones to ketones catalyzed by halogenotin hydride
Shibata, Ikuya,Tsunoi, Shinji,Sakabe, Kumiko,Miyamoto, Shinji,Kato, Hirofumi,Nakajima, Hideto,Yasuda, Makoto,Baba, Akio
, p. 13335 - 13338 (2010)
It's in the tin: The reductive aldol reaction of enones has been established by the Bu2SnClH (cat.)/Ph2SiH2/MeOH system (see scheme). The reaction of enones with α-ketoesters or α-alkoxyketones is highly diastereoselective through a chelation-controlled mechanism. Copyright
Indium hydride catalyzed chemo- and diastereoselective reductive aldol reactions
Ieki, Ryosuke,Miyamoto, Shinji,Tsunoi, Shinji,Shibata, Ikuya
, p. 471 - 474 (2014)
The reductive aldol reaction of enones has been established catalyzed by Br2InOMe (cat.)-MePhSiH2 system where Br2InH acted as an active catalytic species. Addition of 1.0 equivalent of MeOH was essential for catalytic turnover. The system, Br2InOMe(cat.)- MePhSiH2-MeOH, provided highly chemoand diastereoselective reductive aldol reaction of enones with functionalized substrates such as α-bromo carbonyls, α-keto esters and α-alkoxy ketones.
Sonochemical fabrication of Pd/TiO2-nanotubes/Ti plate as a green catalyst for oxidation of alkylarenes and benzyl alcohols
Keshipour, Sajjad,Faraji, Masoud,Asl, Parisa Aboozari
, p. 1423 - 1429 (2019)
A facile and fast strategy has been employed to fabricate Pd nanoparticles supported on TiO2 nanotubes/Ti plate via sonochemical deposition. Microstructure studies showed the homogeneous deposition of Pd nanoparticles on the walls of TiO2 nanotubes/Ti plate. The synthesized plate was applied as a novel catalyst for the oxidation of benzyl alcohol and ethylbenzene derivatives. The results of catalytic experiments demonstrated that the modified plate was an efficient green catalyst for the oxidation of benzyl alcohols to benzoic acid derivatives in H2O. The oxidation of alkylarenes was carried out in EtOH:H2O (1:1) ended up with the formation of the corresponding ketone as the sole product. High yields and excellent selectivities were obtained for the oxidation reactions in green solvents using green oxidant. Superior catalytic activity, easy catalyst recovery, and reusability of the catalyst are some advantages of the modified PdNPs/TiO2 nanotubes/Ti plate, indicating a potential application of the catalyst in the industrial oxidation reactions.
Nickel-Catalyzed Reductive Acylation of Carboxylic Acids with Alkyl Halides and N-Hydroxyphthalimide Esters Enabled by Electrochemical Process
Guo, Lin,Xia, Raymond Yang,Xia, Wujiong,Yang, Chao,Zhang, Haoxiang,Zhou, Xiao
supporting information, (2022/03/31)
A sustainable Ni-catalyzed reductive acylation reaction of carboxylic acids via an electrochemical pathway is presented, affording a variety of ketones as major products. The reaction proceeds at ambient temperature using unactivated alkyl halides and N-hydroxyphthalimide (NHP) esters as coupling partners, which exhibits several synthetic advantages, including mild conditions and convenience of amplification (58% yield for 6 mmol scale reaction). (Figure presented.).
Engineering the large pocket of an (S)-selective transaminase for asymmetric synthesis of (S)-1-amino-1-phenylpropane
Liu, He,Wang, Hualei,Wei, Dongzhi,Xie, Youyu,Xu, Feng,Xu, Xiangyang,Yang, Lin
, p. 2461 - 2470 (2021/04/22)
Amine transaminases offer an environmentally benign chiral amine asymmetric synthesis route. However, their catalytic efficiency towards bulky chiral amine asymmetric synthesis is limited by the natural geometric structure of the small pocket, representing a great challenge for industrial applications. Here, we rationally engineered the large binding pocket of an (S)-selective ?-transaminase BPTA fromParaburkholderia phymatumto relieve the inherent restriction caused by the small pocket and efficiently transform the prochiral aryl alkyl ketone 1-propiophenone with a small substituent larger than the methyl group. Based on combined molecular docking and dynamic simulation analyses, we identified a non-classical substrate conformation, located in the active site with steric hindrance and undesired interactions, to be responsible for the low catalytic efficiency. By relieving the steric barrier with W82A, we improved the specific activity by 14-times compared to WT. A p-p stacking interaction was then introduced by M78F and I284F to strengthen the binding affinity with a large binding pocket to balance the undesired interactions generated by F44. T440Q further enhanced the substrate affinity by providing a more hydrophobic and flexible environment close to the active site entry. Finally, we constructed a quadruple variant M78F/W82A/I284F/T440Q to generate the most productive substrate conformation. The 1-propiophenone catalytic efficiency of the mutant was enhanced by more than 470-times in terms ofkcat/KM, and the conversion increased from 1.3 to 94.4% compared with that of WT, without any stereoselectivity loss (ee > 99.9%). Meanwhile, the obtained mutant also showed significant activity improvements towards various aryl alkyl ketones with a small substituent larger than the methyl group ranging between 104- and 230-fold, demonstrating great potential for the efficient synthesis of enantiopure aryl alkyl amines with steric hindrance in the small binding pocket.