100-81-2Relevant articles and documents
Relationships between structure and action of primary amines and amino acids in the inhibition of trypsin
Mix,Trettin,Guelzow
, p. 52 - 60 (1965)
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Pieper
, p. 129 (1869)
Bifunctional N-Doped Co@C Catalysts for Base-Free Transfer Hydrogenations of Nitriles: Controllable Selectivity to Primary Amines vs Imines
Long, Jilan,Shen, Kui,Li, Yingwei
, p. 275 - 284 (2017)
The transfer hydrogenation of nitriles is an important and alternative strategy to produce primary amines or imines, both of which play a crucial role in the synthesis of fine chemicals and pharmaceuticals. Nevertheless, developing highly active bifunctional catalyst system with controllable selectivity for these reactions still remains a huge challenge. In this study, we presented a bifunctional N-doped Co@C catalyst system (Co@NC) for the selective transfer hydrogenation of nitriles into either primary amines or imines. The Co@NC was prepared by the direct pyrolysis of an N-containing Co-MOF under an inert atmosphere, where the N-containing ligands could be transformed into highly graphitic N-doped carbon, endowing the catalysts with high-density special basic sites, while the Co2+ ions were reduced to uniform Co nanoparticles which were dispersed on or embedded in N-doped graphitic structures. Under base-free conditions with isopropyl alcohol as both proton donor and solvent, the optimized Co@NC-900 (obtained at 900 °C) catalyst could convert nitriles into primary amines or imines at will with surprising selectivities (mostly higher than 90%), depending on the solvent volume added to the reaction systems. Furthermore, a possible reaction mechanism was proposed. The N-derived basic sites on Co@NC could play a role similar to that of the base additives, which not only inhibit the formation of polyamine or prevent the products stacked on the surface of catalysts but also effectively promote the transfer hydrogenation of nitriles. The generated corresponding primary imines could controllably attack the primary imine intermediates to form imines by adjusting the concentration of Co@NC. It is clear that this strategy offers a high-performance catalyst system for base-free transfer hydrogenations of nitriles to selectively produce primary amines vs imines.
A ppm level Rh-based composite as an ecofriendly catalyst for transfer hydrogenation of nitriles: Triple guarantee of selectivity for primary amines
Liu, Lei,Li, Jifan,Ai, Yongjian,Liu, Yuhong,Xiong, Jialiang,Wang, Hongdong,Qiao, Yijun,Liu, Wenrui,Tan, Shanchao,Feng, Shaofei,Wang, Kunpeng,Sun, Hongbin,Liang, Qionglin
, p. 1390 - 1395 (2019)
Hydrogenation of nitriles to afford amines under mild conditions is a challenging task with an inexpensive heterogeneous catalyst, and it is even more difficult to obtain primary amines selectively because of the accompanying self-coupling side reactions. An efficient catalytic system was designed as Fe3O4@nSiO2-NH2-RhCu@mSiO2 to prepare primary amines through the transfer hydrogenation of nitrile compounds with economical HCOOH as the hydrogen donor. The loading of rhodium in the catalyst could be at the ppm level, and the TOF reaches 6803 h-1 for Rh. This catalytic system has a wide substrate range including some nitriles that could not proceed in the previous literature. The experimental results demonstrate that the excellent selectivity for primary amines is guaranteed by three tactics, which are the strong active site, the inhibition of side products by the hydrogen source and the special pore structure of the catalyst. In addition, the catalyst could be reused ten times without activity loss through convenient magnetic recovery.
Method for preparing primary amine by catalytically reducing nitrile compounds through nano-porous palladium catalyst
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Paragraph 0069-0072, (2021/05/29)
The invention belongs to the technical field of heterogeneous catalysis, and provides a method for preparing primary amine by catalytically reducing nitrile compounds with a nano-porous palladium catalyst. According to the invention, aromatic and aliphatic nitrile compounds are adopted as raw materials, nano-porous palladium is adopted as a catalyst, ammonia borane is adopted as a hydrogen source, no additional additive is added, and selective hydrogenation is performed to prepare the corresponding primary amine. The method provided by the invention has the beneficial effects of mild reaction conditions, no additive, environmental protection, no need of hydrogen, simple operation, stable hydrogen source, safety, harmlessness, high conversion rate, high selectivity and good catalyst stability, and makes industrialization possible.
Self-regulated catalysis for the selective synthesis of primary amines from carbonyl compounds
Fan, Xiaomeng,Gao, Jin,Gao, Mingxia,Jia, Xiuquan,Ma, Jiping,Xu, Jie
supporting information, p. 7115 - 7121 (2021/09/28)
Most current processes for the general synthesis of primary amines by reductive amination are performed with enormously excessive amounts of hazardous ammonia. It remains unclear how catalysts should be designed to regulate amination reaction dynamics at a low ammonia-to-substrate ratio for the quantitative synthesis of primary amines from the corresponding carbonyl compounds. Herein we show a facile control of the reaction selectivity in the layered boron nitride supported ruthenium catalyzed reductive amination reaction. Specifically, locating ruthenium to the edge surface of layered boron nitride leads to an increased hydrogenation activity owing to the enhanced interfacial electronic effects between ruthenium and the edge surface of boron nitride. This enables self-accelerated reductive amination reactions which quantitatively synthesize structurally diverse primary amines by reductive amination of carbonyl compounds with twofold ammonia. This journal is
