- Method for catalyzing N-alkylation of aminopyridine
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The invention discloses a method for catalyzing N-alkylation of aminopyridine. The method comprises the step of reacting an aminopyridine compound with an alkylation raw material in the presence of a heterogeneous catalyst to obtain an N-alkylated aminopyridine compound. The alkylation reaction has high activity and selectivity, is simple to operate and low in catalyst price, does not need other reaction steps, is beneficial to large-scale industrial production, and compared with previous reports, does not need to use a large amount of noble metals, can be continuously carried out, and does not use other expensive organic raw materials or reducing agents in the process. Generation of a large amount of organic waste liquid and solid waste is avoided, and collection operation of process products is simple.
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Paragraph 0087-0091
(2021/08/07)
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- Nickel-Catalyzed Amination of Aryl Chlorides with Amides
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A nickel-catalyzed amination of aryl chlorides with diverse amides via C-N bond cleavage has been realized under mild conditions. A broad substrate scope with excellent functional group tolerance at a low catalyst loading makes the protocol powerful for synthesizing various aromatic amines. The aryl chlorides could selectively couple to the amino fragments rather than the carbonyl moieties of amides. Our protocol complements the conventional amination of aryl chlorides and expands the usage of inactive amides.
- Li, Jinpeng,Huang, Changyu,Wen, Daheng,Zheng, Qingshu,Tu, Bo,Tu, Tao
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supporting information
p. 687 - 691
(2021/01/09)
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- Preparation method of N-alkylated derivative of primary amine compound
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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.
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Paragraph 0021; 0046
(2021/07/09)
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- Synergistic catalysis of Cu+/Cu0 for efficient and selective N-methylation of nitroarenes with para-formaldehyde
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In this paper, an inexpensive heterogeneous copper nanoparticles catalyst derived from CuAl-layered double hydroxide via an in situ topotactic transformation process was developed. Cu nanoparticles with uniform size were homogeneously dispersed on amorphous Al2O3 with strong metal-support interaction. Characterization results reveals that the Cu0 and Cu+ were simultaneously formed with Cu+ species as the dominant sites on the surface during the reduction process. The resultant catalyst Cu/Al2O3 demonstrates high catalytic activity, selectivity and durability for the reductive N-methylation of easily available nitroarenes in a cost-efficient, environmentally friendly and cascade manner. A broad spectrum of nitroarenes could be efficiently N-methylated to their corresponding N,N-dimethyl amines with good compatibility of various functional groups. The protocol is also applicable for the late-stage functionalization of biologically and pharmaceutically active nitro molecules. A structure-function relationship discloses that Cu0 and Cu+ sites on the surface pronouncedly boosts the reaction efficiency in a synergistic manner, in which Cu0 could facilitate H2 production and N-methylation of anilines, while Cu+ is considerably more active and participates in the overall process of the selective N-methylation of nitroarenes. Moreover, the catalyst also showed a strong stability and could be easily separated for successive reuses without an appreciable loss in activity and selectivity.
- Dong, Xiaosu,Wang, Zhaozhan,Yuan, Youzhu,Yang, Yong
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p. 304 - 313
(2019/07/02)
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- Method for N-methylation reaction of nitro-compound
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The invention discloses a method for direct N-methylation reaction by taking a nitro-compound as a raw material. The method adopts a Cu-based catalyst and polyformaldehyde and can realize the direct N-methylation reaction of the nitro-compound under mild conditions.
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Paragraph 0050-0054
(2019/01/23)
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- Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
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The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
- Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
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supporting information
p. 714 - 718
(2015/03/18)
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- The Role of Substituent Effects in Tuning Metallophilic Interactions and Emission Energy of Bis-4-(2-pyridyl)-1,2,3-triazolatoplatinum(II) Complexes
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The photoluminescence spectra of a series of 5-substituted pyridyl-1,2,3-triazolato PtII homoleptic complexes show weak emission tunability (ranging from λ=397-408 nm) in dilute (10-6 M) ethanolic solutions at the monomer level and strong tunability in concentrated solutions (10-4 M) and thin films (ranging from λ=487-625 nm) from dimeric excited states (excimers). The results of density functional calculations (PBE0) attribute this "turn-on" sensitivity and intensity in the excimer to strong Pt-Pt metallophilic interactions and a change in the excited-state character from singlet metal-to-ligand charge transfer (1MLCT) to singlet metal-metal-to-ligand charge transfer (1MMLCT) emissions in agreement with lifetime measurements. Turn-on tunability: A series of bis-4-(2-pyridyl)-1,2,3-triazolatoplatinum(II) complexes display variable emission tunability. At low concentration, the emission can be tuned only slightly by changing the nature of the substituent but at higher concentrations tunability is enhanced. This "turn-on" sensitivity in the excimeric emission is attributed to strong Pt-Pt metallophilic interactions and a change in the excited-state character.
- Prabhath, M. R. Ranga,Romanova, Julia,Curry, Richard J.,Silva, S. Ravi P.,Jarowski, Peter D.
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supporting information
p. 7949 - 7953
(2015/06/30)
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- N -heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed amination between aryl chlorides and amides
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We report herein that amides are excellent N-sources in the NHC-Pd(II)-Im complex 1 catalyzed amination of aryl chlorides. In the presence of KO tBu, various aryl chlorides and amides can react smoothly to give the corresponding aminated products in moderate to almost quantitative yields at room temperature within 6 h.
- Chen, Wen-Xin,Shao, Li-Xiong
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p. 9236 - 9239,4
(2012/12/12)
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- N -heterocyclic carbene-palladium(II)-1-methylimidazole complex catalyzed amination between aryl chlorides and amides
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We report herein that amides are excellent N-sources in the NHC-Pd(II)-Im complex 1 catalyzed amination of aryl chlorides. In the presence of KO tBu, various aryl chlorides and amides can react smoothly to give the corresponding aminated products in moderate to almost quantitative yields at room temperature within 6 h.
- Chen, Wen-Xin,Shao, Li-Xiong
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p. 9236 - 9239
(2013/01/15)
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- Simplifying pyridoxal: Practical methods for amino acid dynamic kinetic resolution
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Figure presented Metal complexes of picolinaldehyde are identified as low-cost and environmentally benign catalysts, providing high reaction rates and turnovers for the racemization of amino acids. These pyridoxal surrogates demonstrate activity toward a variety of amino acid esters. Applications to chemoenzymatic dynamic kinetic resolutions provide access to amino acids in high yields and with excellent enantioselectivities, demonstrating their compatibility with protease-mediated transformations.
- Felten, Albert E.,Zhu, Gangguo,Aron, Zachary D.
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supporting information; experimental part
p. 1916 - 1919
(2010/07/06)
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- Simple, efficient protocols for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine
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Simple and efficient procedures for the Pd-catalyzed cross-coupling reaction of aryl chlorides and dimethylamine are described. At room temperature with a strong base, t-BuXPhos is employed as the supporting ligand; at 110 °C with a weak base, XPhos is employed as the supporting ligand. In each of these cases, commercially available solutions constitute the source of the dimethylamine, and recently disclosed precatalysts constitute the source of the ligand and Pd. This work further expands the utility of these precatalysts in reactions that benefit from an easily activated source of L1Pd(0).
- Lee, Brian K.,Biscoe, Mark R.,Buchwald, Stephen L.
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supporting information; experimental part
p. 3672 - 3674
(2009/10/04)
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- Syntheses of 5,5-disubstituted 2,2'-bipyridines
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New and improved syntheses of 5,5'-donor-functionalized 2,2'-bipyridines are reported with the 5,5'-donors being -NH2 (4), -NMe2 (5), -CN (6), and - NCS (7). A new route for 4 and 5 is based on the coupling of 2-chloro-5- amino-pyridine in the presence of NiCl2 · 6 H2O/PPh3/Zn in DMF (NiCRA) · 6 was obtained by a dehydration treatment of 5,5'-dicarboxamide-2,2'- bipyridine with (F3CCO)2O and P4O10. The new ligand 7 is prepared from 4 and SCCl2.
- Janiak, Christoph,Deblon, Stephan,Wu, He-Ping
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p. 3341 - 3352
(2007/10/03)
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