85404-21-3Relevant articles and documents
N,N-Chelate nickel(II) complexes bearing Schiff base ligands as efficient hydrogenation catalysts for amine synthesis
Xu, Mengyin,Wang, Yang,Zhou, Yifeng,Yao, Zi-Jian
, (2021/12/09)
Five N, N-chelate nickel (II) complexes bearing N-(2-pyridinylmethylene)-benzylamine ligands with different substituent groups were synthesized in good yields. The nickel complexes exhibited prominent catalytic efficiency toward amine synthesis from nitro compounds by using NaBH4 or H2 as hydrogen source through two catalytic systems. Various amines with different substituents were obtained in moderate to excellent yields. All substrates with electron-donating and electron-withdrawing properties were tolerated in the two reduction systems. Given the efficient catalytic activity, broad substance scope, and mild reduction conditions, the nickel catalysts have potential applications in industrial production.
Method for preparing amine through catalytic reduction of nitro compound by cyclic (alkyl) (amino) carbene chromium complex
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Paragraph 0015, (2021/04/17)
The cyclic (alkyl) (amino) carbene chromium complex is prepared from corresponding ligand salt, alkali and CrCl3 and used for catalyzing pinacol borane to reduce nitro compounds in an ether solvent under mild conditions to generate corresponding amine. The method for preparing amine has the advantages of cheap and accessible raw materials, mild reaction conditions, wide substrate application range, high selectivity and the like, and is simple to operate.
Synthesis, Structure, and Catalytic Hydrogenation Activity of [NO]-Chelate Half-Sandwich Iridium Complexes with Schiff Base Ligands
Lv, Wen-Rui,Li, Rong-Jian,Liu, Zhen-Jiang,Jin, Yan,Yao, Zi-Jian
, p. 8181 - 8188 (2021/05/26)
A series of N,O-coordinate iridium(III) complexes with a half-sandwich motif bearing Schiff base ligands for catalytic hydrogenation of nitro and carbonyl substrates have been synthesized. All iridium complexes showed efficient catalytic activity for the hydrogenation of ketones, aldehydes, and nitro-containing compounds using clean H2 as reducing reagent. The iridium catalyst displayed the highest TON values of 960 and 950 in the hydrogenation of carbonyl and nitro substrates, respectively. Various types of substrates with different substituted groups afforded corresponding products in excellent yields. All N,O-coordinate iridium(III) complexes 1-4 were well characterized by IR, NMR, HRMS, and elemental analysis. The molecular structure of complex 1 was further characterized by single-crystal X-ray determination.
Biocatalysed synthesis of chiral amines: continuous colorimetric assays for mining amine-transaminases
Gourbeyre, Léa,Heuson, Egon,Charmantray, Franck,Hélaine, Virgil,Debard, Adrien,Petit, Jean-Louis,de Berardinis, Véronique,Gefflaut, Thierry
, p. 904 - 911 (2021/02/26)
In the course of our research aimed at the design of new biocatalytic processes for the enantioselective synthesis of chiral amines, we have developed new continuous assays for the screening of amine-transaminase collections. These assays are based on the use of hypotaurine as an irreversible amine donor. This β-aminosulfinic acid is converted upon transamination into 2-oxoethylsulfinic acid, which instantaneously decomposes into acetaldehyde and sulfite ions that can be easily detected by spectrophotometry using Ellman's reagent. Two complementary assays were developed based on this titration method. Firstly, a direct assay allowed detection of various transaminases able to use hypotaurine as an amino donor. In a second coupled assay,l-alanine is used as a generic donor substrate of amine-transaminases and is regenerated using an auxiliary hypotaurine-transaminase. The powerful and complementary nature of both assays was demonstrated through the screening of a collection of 549 amine-transaminases from biodiversity, thus allowing the discovery of a variety of valuable new biocatalysts for use in synthetic processes.
PROCESS FOR PREPARING PRIMARY AMINES FROM ALCOHOLS
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Page/Page column 13, (2020/06/10)
A process for preparing a primary amine by reacting an alcohol with ammonia in the present of a metal catalyst comprising metal nanoparticles, wherein the metal nano-particles comprises at least one transition metal in elemental form and/or at least one transition metal compound and carbonaceous species are deposited on the metal nan-oparticles.
Half-sandwiched ruthenium complex containing carborane schiff base ligand and preparation and application thereof
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Paragraph 0067-0071, (2020/12/09)
The invention relates to a half-sandwiched ruthenium complex containing a carborane schiff base ligand and a preparation and an application thereof. The preparation method specifically comprises the following steps; i) dissolving o-carborane formaldehyde and aromatic amine in an organic solvent, carrying out reaction at 60-100 DEG C for 8-12h, cooling to room temperature after the reaction; ii) adding n-butyllithium, carrying out reaction at room temperature for 1.5-2.5h; ii) adding phellandrene ruthenium chloride dimer, carrying out reaction at room temperature for 3-6h, and obtaining the half-sandwiched ruthenium complex through separation. The half-sandwiched ruthenium complex is applied to catalyze transfer hydrogenation reaction of nitrile compounds. Compared with the prior art, the complex of the present invention is not sensitive to air and water, has stable properties, and shows high-efficiency catalytic activity in catalyzing the transfer hydrogenation reaction of nitrile compounds. The preparation method of the complex is simple and green, high in yield, mild in reaction conditions and good in universality.
One-pot reductive amination of carboxylic acids: a sustainable method for primary amine synthesis
Coeck, Robin,De Vos, Dirk E.
supporting information, p. 5105 - 5114 (2020/08/25)
The reductive amination of carboxylic acids is a very green, efficient and sustainable method for the production of (bio-based) amines. However, with current technology, this reaction requires two to three reaction steps. Here, we report the first (heterogeneous) catalytic system for the one-pot reductive amination of carboxylic acids to amines, with solely H2 and NH3 as the reactants. This reaction can be performed with relatively cheap ruthenium-tungsten bimetallic catalysts in the green and benign solvent cyclopentyl methyl ether (CPME). Selectivities of up to 99% for the primary amine could be achieved at high conversions. Additionally, the catalyst is recyclable and tolerant for common impurities such as water and cations (e.g. sodium carboxylate).
Ambient-Temperature Synthesis of Primary Amines via Reductive Amination of Carbonyl Compounds
Xie, Chao,Song, Jinliang,Hua, Manli,Hu, Yue,Huang, Xin,Wu, Haoran,Yang, Guanying,Han, Buxing
, p. 7763 - 7772 (2020/08/21)
Efficient synthesis of primary amines via low-temperature reductive amination of carbonyl compounds using NH3 and H2 as the nitrogen and hydrogen resources is highly desired and challenging in the chemistry community. Herein, we employed naturally occurring phytic acid as a renewable precursor to fabricate titanium phosphate (TiP)-supported Ru nanocatalysts with different reduction degrees of RuO2 (Ru/TiP-x, x represents the reduction temperature) by combining ball milling and molten-salt processes. Very interestingly, the obtained Ru/TiP-100 had good catalytic performance for the reductive amination of carbonyl compounds at ambient temperature, resulting from the synergistic cooperation of the support (TiP) and the Ru/RuO2 with a suitable proportion of Ru0 (52%). Various carbonyl compounds could be efficiently converted into the corresponding primary amines with high yields. More importantly, the conversion of other substrates with reducible groups could also be achieved at ambient temperature. Detailed investigations indicated that the partially reduced Ru and the support (TiP) were indispensable. The high activity and selectivity of Ru/TiP-100 catalyst originates from the relatively high acidity and the suitable electron density of metallic Ru0.
Rice husk-SiO2supported bimetallic Fe-Ni nanoparticles: as a new, powerful magnetic nanocomposite for the aqueous reduction of nitro compounds to amines
Ghadermazi, Mohammad,Moradi, Setareh,Mozafari, Roya
, p. 33389 - 33400 (2020/09/21)
This paper reports a novel green procedure for immobilization of bimetallic Fe/Ni on amorphous silica nanoparticles extracted from rice husk (RH-SiO2). The heterogeneous nanocomposite (Fe/Ni?RH-SiO2) was identified using SEM, EDX, TEM, BET, H2-TPR, TGA, XRD, VSM, ICP-OES, and FT-IR analyses. The Fe/Ni?RH-SiO2nanocomposite was applied as a powerful catalyst for the reduction of structurally diverse nitro compounds with sodium borohydride (NaBH4) in green conditions. This procedure suggests some benefits such as green chemistry-based properties, short reaction times, non-explosive materials, easy to handle, fast separation and simple work-up method. The catalyst was separated by an external magnet from the reaction mixture and was reused for 9 successive cycles with no detectable changes of its catalytic efficiency.
Environmentally responsible, safe, and chemoselective catalytic hydrogenation of olefins: ppm level Pd catalysis in recyclable water at room temperature
Gallou, Fabrice,Gao, Eugene S.,Lipshutz, Bruce H.,Takale, Balaram S.,Thakore, Ruchita R.
supporting information, p. 6055 - 6061 (2020/10/14)
Textbook catalytic hydrogenations are typically presented as reactions done in organic solvents and oftentimes under varying pressures of hydrogen using specialized equipment. Catalysts new and old are all used under similar conditions that no longer reflect the times. By definition, such reactions are both environmentally irresponsible and dangerous, especially at industrial scales. We now report on a general method for chemoselective and safe hydrogenation of olefins in water using ppm loadings of palladium from commercially available, inexpensive, and recyclable Pd/C, together with hydrogen gas utilized at 1 atmosphere. A variety of alkenes is amenable to reduction, including terminal, highly substituted internal, and variously conjugated arrays. In most cases, only 500 ppm of heterogeneous Pd/C is sufficient, enabled by micellar catalysis used in recyclable water at room temperature. Comparison with several newly introduced catalysts featuring base metals illustrates the superiority of chemistry in water.
