2217-07-4Relevant articles and documents
Nickel-catalysed amination of aryl chlorides using a dihydroimidazoline carbene ligand
Gradel, Benot,Brenner, Eric,Schneider, Rapha?l,Fort, Yves
, p. 5689 - 5692 (2001)
A new arylamination protocol has been developed using a catalyst combination prepared from Ni(acac)2 associated to a sterically hindered dihydroimidazoline carbene ligand. A high efficiency was attained using, in most cases, only 2 mol% Ni/carbene clusters.
Preparation method of N-alkylated derivative of primary amine compound
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Paragraph 0021; 0055, (2021/07/09)
The invention relates to a preparation method of an N-alkylated derivative of a primary amine compound. The method comprises the following steps: uniformly mixing a primary amine compound, an alcohol compound and a catalyst in a reactor, and heating to react for a period of time to generate an N-alkylated substituted tertiary amine compound; wherein the catalyst is a copper-cobalt bimetallic catalyst, and the carrier of the catalyst is Al2O3. According to the method, alcohol is adopted as an alkylating reagent and is low in price and easy to obtain, a byproduct is water, no pollution is caused to the environment, and the overall reaction atom economy is high; the catalyst is simple in preparation method, low in cost, high in reaction activity and good in structural stability; meanwhile, by using the copper-cobalt bimetallic catalyst, the use of strong base additives can be avoided, and the requirement on reaction equipment is low; and the reaction post-treatment is convenient, and the catalyst can be recycled and is environment-friendly.
Heterogeneous Ru/TiO2for hydroaminomethylation of olefins: multicomponent synthesis of amines
An, Jinghua,Gao, Zhuyan,Wang, Yehong,Zhang, Zhixin,Zhang, Jian,Li, Lu,Tang, Bo,Wang, Feng
supporting information, p. 2722 - 2728 (2021/04/21)
Synthesizing aminesviathe hydroaminomethylation (HAM) reaction of olefins, a multicomponent reaction, has been regarded as one of the most attractive methods compared with the traditional methods considering the atom economy and environmental friendliness. However, the use of homogeneous catalysts, complex ligands containing diphosphine or nitrogen, and base or acid additives has severely hampered the utilization of these methods. Herein, an efficient heterogeneous Ru/TiO2-catalyzed HAM reaction of olefins is developed without any additives. Various amines, including secondary and tertiary amines, can be successfully obtained from olefins including aromatic and aliphatic olefins. Systematic studies demonstrate the lower electron density of Ruδ+and the higher number of acid sites of Ru/TiO2, leading to the high HAM reaction activity of olefins. Most importantly, nitrobenzene derivatives can also be transformed to the corresponding products over Ru/TiO2in excellent yields.
Reductive Alkylation of Amines with Carboxylic Ortho Esters
Kadyrov, Renat,Moebus, Konrad
supporting information, p. 3352 - 3357 (2020/07/04)
We have demonstrated for the first time that carboxylic ortho esters could be used as an alkylating agent in the reductive alkylation of amines. A variety of amines, including amino acid esters, were alkylated affording mono-alkylated products with high selectivity in practical to high yields using standard heterogeneous catalysts. By applying acyclic ortho esters alkylation was completed at room temperature. (Figure presented.).
Plasma-Made (Ni0.5Cu0.5)Fe2O4 Nanoparticles for Alcohol Amination under Microwave Heating
Li, Alain You,Dumaresq, Nicolas,Segalla, Andréanne,Braidy, Nadi,Moores, Audrey
, p. 3959 - 3972 (2019/08/12)
Amine N-alkylation is a process involved in the production of a wide range of chemicals. Here we describe the synthesis of well-defined (Ni0.5Cu0.5)Fe2O4 magnetic nanoparticles by plasma induction, and their successful application to amine N-alkylation using alcohols as coupling agents through a borrowing hydrogen pathway. Plasma induction allows precise morphology and size control over nanoparticle synthesis, while allowing the one-pot production of decagram quantities of material. Up to date, such nanoparticles have never been applied for organic reactions. By coupling high-end characterization techniques with catalytic optimization, we showed that small Cu(0) satellite nanoparticles played an essential role in alcohol oxidation, whereas both Ni and Cu were required for the last step of the reaction. Using elemental mapping, we demonstrated that catalyst deactivation occurred through a leaching/re-deposition mechanism of Cu and Ni. The reactions were conducted under microwave conditions, which exerted a positive effect on catalytic activity. Finally, the catalyst was active at low metal loadings (2 mol%) even on the gram-scale, and affording unprecedented TON for this reaction catalyzed by Ni/Cu bimetallic systems (19).
3-hydroxy flavone compound and application thereof
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Paragraph 0043; 0047-0053, (2019/11/28)
The invention belongs to the technical field of biological fluorescence analysis, and particularly relates to a 3-hydroxy flavone compound and an application thereof. The compound is particularly a 4-n,n-dialkylamino-3-hydroxy flavone compound, and when the compound is used as a fluorescent dye, the lipid droplet targeting property is better, and a cytoskeleton is hardly colored. When conjugated structures such as a benzene ring and the like are added to the left side of a molecule of the compound, the emission wavelength of the molecule can be greatly prolonged, and fluorescence crossing of the molecule from yellow to red is realized. The compound can be applied to the aspects of dynamic lipid droplet imaging in cells, lipid droplet growth process imaging, adipose tissue imaging, even simultaneous imaging of intramuscular fat and intermuscular fat in skeletal muscle tissues, and the like, and has important application values in the fields of fluorescent dyes, biological fluorescent labels and the like.
Colloidal and Nanosized Catalysts in Organic Synthesis: XXIII. Reductive Amination of Carbonyl Compounds Catalyzed by Nickel Nanoparticles in a Plug-Flow Reactor
Mokhov, V. M.,Nebykov, D. N.,Paputina, A. N.,Popov, Yu. V.,Shishkin, E. V.
, p. 2333 - 2340 (2020/02/25)
Reductive amination of aldehydes and ketones with primary and secondary amines under catalysis with nickel nanoparticles supported on zeolite X, MgO, or activated carbon in the gas phase or in the gas-liquid system in a plug-flow reactor proceeds at atmospheric pressure of hydrogen with the formation of secondary or tertiary amines in high yield.
N-Alkylation of Aniline and Its Derivatives by Alcohols in the Presence of Copper Compounds
Bayguzina,Musina, Ch. F.,Khusnutdinov
, p. 1652 - 1659 (2019/02/12)
N-Alkyl- and N,N-dialkyl-substituted anilines were obtained in the reaction of aniline and its derivatives with primary and secondary alcohols in the presence of catalysts CuCl2·2H2O, CuBr2 and halomethanes as promoters.
Nano CoCuFe2O4-catalyzed coupling reaction of arylboronic acid with amines and thiols: An atom-economic and ligand-free route to access unsymmetrical amines and sulfides
Moghaddam, Firouz Matloubi,Pourkaveh, Raheleh,Gholamtajari, Milad
, (2018/10/20)
An efficient protocol was developed for the nano CoCuFe2O4-catalyzed C-N and C-S bond formation. By this catalytic system, both amine and sulfide-based structural motifs were formed efficiently in aryl halide-free route. The amination reaction of phenyl boronic acid with various types of amines was conducted under ligand-free conditions, in ethanol as a green solvent at 60°C. Unsymmetrical diaryl/aryl alkyl sulfide synthesis via the coupling reaction of arylboronic acids with thiols was also conducted. The nano cobalt-copper ferrite was used as a heterogenous efficient, inexpensive, magnetically separable and recyclable catalyst that can be used for several cycles.
Direct arylation of tertiary amines via aryne intermediates using diaryliodonium salts
Zhang, Zhiang,Wu, Xunshen,Han, Jianwei,Wu, Wenjun,Wang, Limin
supporting information, p. 1737 - 1741 (2018/04/02)
With a strategy by using diaryliodonium salts as the precursors of benzynes, direct N-arylation of tertiary amines with diaryliodonium salts was reported. Thus, the desired aromatic tertiary amines with a wide range of substituents were synthesized in moderate to excellent yields of 55–91%.
