141120-47-0Relevant academic research and scientific papers
Crystal structure, hirshfeld surface analysis and energy framework study of the nitrone n-benzylidene-n-butylamino-4-β-pyridyl-n-oxide
Bahsas, Ali,Brito, Iván,Cárdenas, Alejandro,Chacón, Cecilia,Cisterna, Jonathan,Delgado, Gerzon E.,Koustnetzov, Vladimir V.,Mora, Asiloé J.
, p. 4865 - 4869 (2020/11/16)
The title compound, C16H16N2O, a potential antiparasitic agent, crystallizes in the orthorhombic Pca21 space group with unit cell parameters a= 9.912(1) ?, b= 9.035(1) ?, c= 15.681(2) ?. The crystalline structure is stabilized by weak C-H···O and C-H···Cg(π) interactions among neighboring molecules producing an efficient packing with 66.0% of occupied space. The C-H···O hydrogen bond keeps the molecules linked into supramolecular chains propagating along the a axis direction with a graph-set notation C(4), which are reinforced by C-H···Cg(π) interactions. Hirshfeld surface analysis of the intermolecular contacts reveal that the most important contributions for the crystal packing are from H··H (55.2%) and H··C/C··H (27.1%) interactions. Energy framework calculations suggest that the contacts formed between molecules are slightly dispersive in nature.
Efficient Co-Catalyzed Double Hydroboration of Nitriles: Application to One-Pot Conversion of Nitriles to Aldimines
Gudun, Kristina A.,Slamova, Ainur,Hayrapetyan, Davit,Khalimon, Andrey Y.
, p. 4963 - 4968 (2020/04/17)
The commercially available and bench-stable Co(acac)2/dpephos system is employed as a precatalyst for selective and efficient room temperature hydroboration of organic nitriles with HBPin to produce a series of N,N-diborylamines [RN(BPin)2], which react in situ with aldehydes to give aldimines. Formation of aldimines from N,N-diborylamines does not require a dehydrating agent, is applicable to a wide range of N,N-diborylamine and aldehyde substrates and is highly chemoselective, being unaffected by various common functional groups, such as alkenes, alkynes, secondary amines, ketones, esters, amides, carboxylic acids, pyridines, nitriles, and nitro compounds. The overall transformation represents a synthetically valuable approach to aldimines from nitriles and can be performed in a sequential one-pot manner, tolerating ester, lactone, carboxamide and unactivated alkene functionalities.
Selective aerobic oxidation of halides and amines with an inorganic-ligand supported zinc catalyst
Wang, Jingjing,Zhai, Yongyan,Wang, Ying,Yu, Han,Zhao, Wenshu,Wei, Yongge
, p. 13323 - 13327 (2018/10/15)
A practical, efficient and environmentally benign catalytic protocol for the oxidative cross-coupling reaction of halides with amines, oxidative self-coupling of amines and oxidation of halides was developed with inorganic-ligand supported ZnPOM (NH4)4[ZnMo6O18(OH)6] using molecular oxygen. This method mainly utilizes an inorganic polymolybdate ligand to support the Zn2+ ion, avoiding the use of complicated organic ligands.
Visible-Light-Driven Photocatalytic Oxidation of Organic Chlorides Using Air and an Inorganic-Ligand Supported Nickel-Catalyst Without Photosensitizers
Yu, Han,Wang, Jingjing,Zhai, Yongyan,Zhang, Mengqi,Ru, Shi,Han, Sheng,Wei, Yongge
, p. 4274 - 4279 (2018/09/10)
Engineering photoredox-triggered chemical transformation via visible light has been an emerging area in organic synthesis. However, most of the well-established photocatalysts are based upon either transition metal complexes involved with noble metals and organic ligands or photosensitive organic dyes, the development of pure inorganic molecular photocatalysts that could provide better stability and durability is greatly retarded. Herein we discover that the Anderson polyoxometalate (POM) Na4[NiMo6O18(OH)6] (1), which consists of pure inorganic framework built from a central NiII core supported by six MoVIO6 inorganic scaffold/ligands, can be used as a powerful photocatalyst. Upon irradiation with visible light (>400 nm), the compound can catalyze, in high efficiency, a wide range of reactions, including the oxidative cross-coupling reaction of chlorides with amines, as well as oxidation of chlorides using molecular oxygen, affording various imines, aldehydes, and ketones, respectively in high selectivity and good yields. Owing to the robust inorganic framework, this catalyst exhibits excellent stability during the catalysis and reusability with little loss of the catalytic activity, thus providing an alternative without use of complicated organic ligands and expensive noble metal-based photosensitizers.
Method for synthesizing imine through cross-coupling of hydroxylation phenanthroline copper complex/O2 catalytic oxidation alcohol and amine
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Paragraph 0017; 0030; 0031, (2017/12/02)
The invention discloses a method for synthesizing imine through cross-coupling of hydroxylation phenanthroline copper complex/O2 catalytic oxidation alcohol and amine. According to the method, an economical and cheap hydroxylation phenanthroline copper complex is selected as a catalyst, green O2 is selected as an oxidizing agent, cross-coupling of alcohol and amine is realized under the condition of normal temperature, alkali and an expensive free radical of nitroxide is prevented from being used, and a series of imine compounds are successfully prepared. The method provided by the invention is high in reaction selectivity and relatively wide in a substrate application range, and has a great industrial application potential.
Mechanochemical lignin-mediated strecker reaction
Dabral, Saumya,Turberg, Mathias,Wanninger, Andrea,Bolm, Carsten,Hernández, José G.
, (2017/02/15)
A mechanochemical Strecker reaction involving a wide range of aldehydes (aromatic, heteroaromatic and aliphatic), amines, and KCN afforded a library of α-aminonitriles upon mechanical activation. This multicomponent process was efficiently activated by li
Transition-Metal-Controlled Inorganic Ligand-Supported Non-Precious Metal Catalysts for the Aerobic Oxidation of Amines to Imines
Yu, Han,Zhai, Yongyan,Dai, Guoyong,Ru, Shi,Han, Sheng,Wei, Yongge
supporting information, p. 13883 - 13887 (2017/10/13)
Most state-of-art transition-metal catalysts usually require organic ligands, which are essential for controlling the reactivity and selectivity of reactions catalyzed by transition metals. However, organic ligands often suffer from severe problems including cost, toxicity, air/moisture sensitivity, and being commercially unavailable. Herein, we show a simple, mild, and efficient aerobic oxidation procedure of amines using inorganic ligand-supported non-precious metal catalysts 1, (NH4)n[MMo6O18(OH)6] (M=Cu2+; Fe3+; Co3+; Ni2+; Zn2+, n=3 or 4), synthesized by a simple one-step method in water at 100 °C, demonstrating that the catalytic activity and selectivity can be significantly improved by changing the central metal atom. In the presence of these catalysts, the catalytic oxidation of primary and secondary amines, as well as the coupling of alcohols and amines, can smoothly proceed to afford various imines with O2 (1 atm) as the sole oxidant. In particular, the catalysts 1 have transition-metal ion core, and the planar arrangement of the six MoVI centers at their highest oxidation states around the central heterometal can greatly enhance the Lewis acidity of catalytically active sites, and also enable the electrons in the center to delocalize onto the six edge-sharing MO6 units, in the same way as ligands in traditional organometallic complexes. The versatility of this methodology maybe opens a path to catalytic oxidation through inorganic ligand-coordinated metal catalysis.
Palladium-catalyzed [4 + 2] cycloaddition of aldimines and 1,4-dipolar equivalents via amphiphilic allylation
Hirata, Goki,Yamada, Naoshi,Sanada, Shohei,Onodera, Gen,Kimura, Masanari
supporting information, p. 600 - 603 (2015/03/04)
The combination of Pd catalyst and diethylzinc with triethylborane promotes the amphiphilic allylation of aldimines with 2,3-bismethylenebutane-1,4-diol derivatives to serve as bis-allylic zwitterion species to form 3,4-bismethylenepiperidines via a formal [4 + 2] cycloaddition reaction. 3,4-Bismethylenepiperidine rings are applicable for the synthesis of isoquinoline derivatives via the Diels-Alder reaction followed by an oxidation reaction with DDQ.
Photoredox-Catalyzed Reductive Coupling of Aldehydes, Ketones, and Imines with Visible Light
Nakajima, Masaki,Fava, Eleonora,Loescher, Sebastian,Jiang, Zhen,Rueping, Magnus
supporting information, p. 8828 - 8832 (2015/11/27)
Ketyl radical and amino radical anions, valuable reactive intermediates for C-C bond-forming reactions, are accessible through a C=O/C=NR umpolung. However, their utilization in catalysis remains largely underdeveloped owing to the high reduction potential of carbonyl compounds and imines. In the context of photoredox catalysis, tertiary amines are commonly employed as sacrificial co-reducing agents. Herein, an additional role of the amine is proposed, in which it is essential for the organocatalytic substrate activation. The combination of photoredox catalysis and carbonyl/imine activation enables the reductive coupling of aldehydes, ketones, and imines under mild reaction conditions.
Facile synthesis of litchi shaped cuprous oxide and its application in the aerobic oxidative synthesis of imines
Bai, Lei,Dang, Zheng
, p. 10341 - 10345 (2015/02/05)
In the present work, uniform litchi shaped cuprous oxide (Cu2O) nanoaggregates were synthesized via a facile method by employing copper(ii) chloride, sodium hydroxide, ethylene glycol and ascorbic acid in the absence of surfactants at room temperature. With further increase of the reaction temperature, broken hollow copper nanoaggregates were obtained. The structure of a Cu2O nanoaggregate was characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), Transmission Electron Microscopy (TEM), Brunauer-Emmett-Teller (BET) analysis and High Resolution Transmission Electron Microscopy (HRTEM). The as-obtained Cu2O nanoaggregates showed efficient catalytic activities in the aerobic oxidative synthesis of imines.
