3233-06-5Relevant articles and documents
METHOD FOR PRODUCING AROMATIC AMINE COMPOUNDS FROM PHENOLS
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Paragraph 0017; 0046, (2021/06/04)
PROBLEM TO BE SOLVED: To provide a method for producing an aromatic amine compound from phenols and amines with a high yield and a high selectivity, which includes ones subjected to polyfunctionalization, under relatively low temperature and relatively low pressure, without using an additive which gives a co-product having high environmental load. SOLUTION: Phenols and hydrogen are introduced into a first catalyst cartridge receiving a solid catalyst containing platinum group elements and continuously hydrogenated into cyclohexanones. The resultant cyclohexanones, along with amines selected from ammonia, primary amines and secondary amines, and hydrogen trapping agents are subsequently introduced into a second catalyst cartridge receiving a solid catalyst containing platinum group elements to continuously produce aromatic amine compounds by dehydration condensation and dehydrogenation with amines. SELECTED DRAWING: Figure 2 COPYRIGHT: (C)2021,JPOandINPIT
Air-stable Organoantimony (III) Perfluoroalkyl(aryl)sulfonate complexes as highly efficient, selective, and recyclable catalysts for C–C and C–N bond-forming reactions
Fan, Qi,Guo, Rui,Li, Ningbo,Ma, Rong,Qiao, Jie,Xu, Li,Xu, Shitang,Xu, Xinhua,Yun, Kemin
, (2021/07/08)
A series of air-stable organoantimony (III) perfluoroalkyl(aryl)sulfonate complexes with an azastibocine framework {t-BuN(CH2C6H4)2SbOSO2C4F9 (2a); [t-BuN(CH2C6/
Continuous Synthesis of Aryl Amines from Phenols Utilizing Integrated Packed-Bed Flow Systems
Ichitsuka, Tomohiro,Kobayashi, Shū,Koumura, Nagatoshi,Sato, Kazuhiko,Takahashi, Ikko
, p. 15891 - 15896 (2020/07/13)
Aryl amines are important pharmaceutical intermediates among other numerous applications. Herein, an environmentally benign route and novel approach to aryl amine synthesis using dehydrative amination of phenols with amines and styrene under continuous-flow conditions was developed. Inexpensive and readily available phenols were efficiently converted into the corresponding aryl amines, with small amounts of easily removable co-products (i.e., H2O and alkanes), in multistep continuous-flow reactors in the presence of heterogeneous Pd catalysts. The high product selectivity and functional-group tolerance of this method allowed aryl amines with diverse functional groups to be selectively obtained in high yields over a continuous operation time of one week.
Enzyme- and ruthenium-catalyzed dynamic kinetic resolution involving cascade alkoxycarbonylations for asymmetric synthesis of 5-Substituted N-Aryloxazolidinones
Zhang, Yang,Xie, Sheng,Yan, Mingdi,Ramstr?m, Olof
, p. 138 - 144 (2019/04/10)
Asymmetric synthesis of N-aryloxazolidinones via dynamic kinetic resolution was developed. A ruthenium-based catalyst was used in the racemization of β-anilino alcohols, while Candida antarctica lipase B (CAL-B) was applied for two selective alkoxycarbony
Bifunctional organocatalysts for the conversion of CO2, epoxides and aryl amines to 3-aryl-2-oxazolidinones
Xie, Ya-Fei,Guo, Cheng,Shi, Lei,Peng, Bang-Hua,Liu, Ning
, p. 3497 - 3506 (2019/04/14)
A route to synthesize 3-aryl-2-oxazolidinones is developed, which is achieved through a three component reaction between CO2, aryl amines, and epoxides with a binary organocatalytic system composed of organocatalysts and DBU (1,8-diazabicyclo[5.4.0]undec-7-ene). The method allows wide scopes of epoxide and aryl amine substrates with various functional groups under mild reaction conditions. The control experiments indicate that a cyclic carbonate is formed via cycloaddition of epoxides with CO2, which further reacts with the β-amino alcohol originating from epoxides and aryl amines, resulting in the formation of 3-aryl-2-oxazolidinones finally.
Aluminium Oxide Supported on SBA-15 Molecular Sieves as Potential Lewis Acid Catalysts for Epoxide Ring Opening Using Aniline
Yadav, Rekha,Muralidhar, Akhila,Shamna,Aghila,Gurrala, Lakshmiprasad,Sakthivel, Ayyamperumal
, p. 1407 - 1415 (2018/03/28)
Abstract: A series of aluminium oxide (Al2O3)-supported SBA-15 molecular sieves were prepared using a one-step wet-impregnation method. Powder X-ray diffraction, nitrogen adsorption/desorption, infrared spectroscopy and ammonia TPD were used to investigate the structures and chemical natures of the surface-bound species. The FT-IR studies of metal-impregnated SBA-15 materials revealed strong covalent interaction of Al2O3 on SBA-15 materials with strong Lewis acidic properties, evident from ammonia-TPD studies. The metal oxide-supported SBA-15 catalysts are active for epoxide ring opening with aniline at room temperature, and showed remarkably high stability and selectivity towards mono-alkylated products (about 86%) viz., 1-(phenylamino)propan-2-ol and 2-(phenylamino)propan-1-ol. The catalytic activities remained intact after several recycles. The observed activities and selectivities were compared with other metal oxide-loaded SBA-15 catalysts obtained by similar preparation methods. Graphical Abstract: Aluminium oxide supported SBA-15 molecular sieves were prepared using a one-step wet-impregnation method. The materials showed strong Lewis acidic sites and promising catalytic activity for epoxide ring opening with aniline at room temperature. [Figure not available: see fulltext.]
Tailored Cobalt-Catalysts for Reductive Alkylation of Anilines with Carboxylic Acids under Mild Conditions
Liu, Weiping,Sahoo, Basudev,Spannenberg, Anke,Junge, Kathrin,Beller, Matthias
supporting information, p. 11673 - 11677 (2018/09/10)
The first cobalt-catalyzed hydrogenative N-methylation and alkylation of amines with readily available carboxylic acid feedstocks as alkylating agents and H2 as ideal reductant is described. Combination of tailor-made triphos ligands with cobalt(II) tetrafluoroborate significantly improved the efficiency, thus promoting the reaction under milder conditions. This novel protocol allows for a broad substrate scope with good functional group tolerance, even in the presence of reducible alkenes, esters, and amides.
The synthesis of new 1,3-oxazolidines and 1,3-oxazinanes containing (η6-arene)tricarbonylchromium group based on condensation between aldehydes and amino alcohols
Artemov,Sazonova,Krylova,Zvereva,Pechen,Fukin,Cherkasov,Faerman,Grishina, N. Yu.
, p. 884 - 892 (2018/08/28)
The condensation reactions of β- and γ-amino alcohols containing phenyl or (η6-arene) tricarbonylchromium substituent with formaldehyde, acetaldehyde, benzaldehyde, and (η6-benzaldehyde)tricarbonylchromium were studied. The resulting 1,3-oxazolidine and 1,3-oxazinane products were isolated in a pure form and identified by different physicochemical methods. The effect of (η6-arene)tricarbonylchromium moiety on the reaction process was demonstrated.
Synthesis and structure of an air-stable bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate and its application in catalytic epoxide ring-opening reactions
Li, Ningbo,Wang, Lingxiao,Wang, Haojiang,Qiao, Jie,Zhao, Wenjie,Xu, Xinhua,Liang, Zhiwu
, p. 1033 - 1039 (2018/02/06)
An air-stable mononuclear complex of bis(pentamethylcyclopentadienyl) zirconium pentafluorbezenesulfonate was successfully synthesized by treating C6F5SO3Ag with [(CH3)5Cp]2ZrCl2, which showed the cationic uninuclear structure of [{(CH3)5Cp}2Zr(CH3CN)2(H2O)][OSO2C6F5]2·CH3CN (1) confirmed by the X-ray analysis. Complex 1 was also characterized by other techniques and found to have the good nature of air-stability, water tolerance, thermally-stability and strong Lewis-acidity. Moreover, the complex showed high catalytic activity and recyclability in catalytic epoxide ring-opening reactions by amines or alcohols. This catalytic system affords a simple and efficient approach for synthesis of β-amino alcohols or β-alkoxy alcohols.
Selective C-N coupling reaction of diaryliodonium salts and dinucleophiles
Ma, Chang,Wu, Xufeng,Zeng, Qingle,Zhou, Lihong,Huang, Yi
supporting information, p. 2873 - 2877 (2017/04/14)
N-Aryl-α-amino amides including their chiral isomers have demonstrated important applications as pharmaceutical drugs; however, to date, a one-step synthetic route for them still remains to be developed. Herein, an efficient ligand-free copper-catalyzed selective C-N coupling reaction of diaryliodonium salts and dinucleophiles under mild conditions was realized. Diaryliodonium salts prefer to react with dinucleophiles at the site of stronger alkalic amino groups. Thus, a general aliphatic amino-selective N-arylation of α-amino amides was disclosed. Additionally, copper-catalyzed N-arylation of diaryliodonium salts afforded the same products as obtained via palladium-catalyzed reactions of aryl halides.
