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Chinese Chemical Letters 2010年第1期21卷 47-50页

作者： Heshmatollah Alinezhad Mahmood Tajbakhsh Neda Hamidi Faculty of Chemistry Mazandaran UniversityBabolsarIran

A simple and convenient procedure for the preparation of amines from aldehydes and ketones with sodium borohydride activated by silica chloride as a catalyst under solvent-free conditions is described.A variety of aliphatic and aromatic aldehydes,ketones and amines when mixed with NaBH;/silica chloride at room temperature,afforded excellent yield of the corresponding amines.

关键词： reductive amination Silica chloride Solvent-free conditions Sodium borohydride

reductive amination of Aldehydes and Ketones with Primary Amines by Using Lithium Amidoborane as Reducing Reagent

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Chinese Journal of Chemistry 2012年第8期30卷 1775-1780页

作者：徐维亮郑学丽吴国涛陈萍 Department of Chemistry National University of Singapore117543 Singapore Key Lab of Green Chemistry and Technology Ministry of Educationthe Institute of Homogeneous CatalysisCollege of ChemistrySichuan UniversityChengduSiehuan 610064China Dalian Institute of Chemical Physics DalianLiaoning 116023China

A variety of secondary amines were obtained in high isolated yields in the reductive amination of aldehydes and ketones by using lithium amidoborane as reducing agent. Compared to ammonia borane, lithium amidoborane h... 详细信息

关键词： lithium amidoborane reductive amination primary amines aldehydes ketones

Practical N-alkylation via homogeneous iridium-catalyzed direct reductive amination

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Science China Chemistry 2023年第2期66卷 518-525页

作者： Jing Wang Wenji Wang Xiongyu Yang Jingwen Liu Haizhou Huang Mingxin Chang College of Chemistry&Pharmacy Northwest A&F UniversityYangling12100China College of Plant Protection Shaanxi Research Center of Biopesticide Engineering&TechnologyNorthwest A&F UniversityYangling712100China

Direct reductive amination(DRA)is one of the most efficient methods for amine *** we report a practical homogeneous DRA procedure utilizing iridium *** simple,readily available and inexpensive PPh_(3)and alike ligands along with iridium at a low loading,aldehydes and ketones reductively coupled with primary and secondary amines to efficiently form structurally and functionally diverse amine products,including a set of drugs and compounds from late-stage *** reaction conditions were exceptionally mild and additive-free,in which oxygen,moisture,polar protic groups and multiple other functional groups were *** targeted products,this methodology is especially versatile for offering multiple possible synthetic *** 10 gram-scale synthesis further demonstrated the potential and promise of this procedure in practical amine *** studies reveal an“outer-sphere”H-addition pathway,in whichπ-πinteractions and H-bonding play important roles.

关键词： homogeneous catalysis hydrogenation Iridium catalysis N-alkylation reductive amination

Efficient light-driven reductive amination of furfural to furfurylamine over ruthenium-cluster catalyst

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Journal of Energy Chemistry 2023年第1期76卷 239-248,I0007页

作者： Zhen Xue Shasha Wu Yujing Fu Lan Luo Min Li Zhenhua Li Mingfei Shao Lirong Zheng Ming Xu Haohong Duan State Key Laboratory of Chemical Resource Engineering Beijing University of Chemical TechnologyBeijing 100029China Department of Chemistry TsinghuaUniversityBeijing 10084China Institute of High Energy Physics The Chinese Academy of SciencesBeijing 100049China

Selective reductive amination of carbonyl compounds with high activity is very essential for the chemical and pharmaceutical industry,but scarcely successful paradigm was reported via efficient photocatalytic ***,the ultrasmall Ru nanoclusters(~0.9 nm)were successfully fabricated over P25 support with positive charged Ru^(δ+)species at the interface.A new route was developed to achieve the furfural(FAL)to furfurylamine(FAM)by coupling the light-driven reductive amination and hydrogen transfer of ethanol over this type ***,the photocatalytic activity and selectivity are strongly dependent on the particle size and electronic structure of *** Ru^(δ+)species at the interface promote the formation of active imine intermediates;moreover,the Ru nanoclusters facilitate the separation efficiency of electrons and holes as well as accelerate the further hydrogenation of imine intermediates to product primary *** contrast Ru particles in larger nanometer size facilitate the formation of the furfuryl alcohol and excessive hydrogenation *** addition,the coupling byproducts can be effectively inhibited via the construction of *** study offers a new path to produce the primary amines from biomass-derived carbonyl compounds over hybrid semiconductor/metal-clusters photocatalyst via light-driven tandem catalytic process.

关键词： Furfural reductive amination Ru nanoclusters Hydrogen transfer Photocatalysis

Selectively reductive amination of levulinic acid with aryl amines to N-substituted aryl pyrroles

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Green Energy & Environment 2023年第2期8卷 438-443页

作者： Cailing Wu Mengjie Lou Mingming Sun Huiyong Wang Zhiyong Li Jikuan Qiu Jianji Wang Zhimin Liu Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals School of Chemistry and Chemical EngineeringKey Laboratory of Green Chemical Media and ReactionsMinistry of EducationHenan Normal UniversityXinxiangHenan453000China Beijing National Laboratory for Molecular Sciences Key Laboratory of ColloidInterface and ThermodynamicsCAS ResearchInstitute of ChemistryChinese Academy of SciencesBeijing100190China

Synthesizing nitrogen(N)-containing molecules from biomass derivatives is a new strategy for production of this kind of ***,for the first time we present the synthesis of N-substituted aryl pyrroles via reductive amination/cyclization of levulinic acid(LA)with primary aromatic amines and hydrosilanes(e.g.,PMHS)over Cs F,and a series of N-substituted aryl pyrroles could be obtained in good to excellent yields at 120○*** mechanism investigation indicates that the reaction proceeds in two steps:the cyclization between amine and LA occurs first to form intermediate 5-methyl-N-alkyl-1,3-dihydro-2H-pyrrolones and their isomeride(B),and then the chemo-and region-selective reduction of intermediates take place to produce the final *** approach for synthesis of N-substituted aryl pyrroles can be performed under mild and green conditions,which may have promising applications.

关键词： Biomass Levulinic acid reductive amination Pyrrole

reductive amination of ketones with ammonium catalyzed by a newly identified Brevibacterium epidermidis strain for the synthesis of(S)-chiral amines

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Chinese Journal of Catalysis 2018年第10期39卷 1625-1632页

作者： Qing‐Hua Li Yuan Dong Fei‐Fei Chen Lei Liu Chun‐Xiu Li Jian‐He Xu Gao‐Wei Zheng State Key Laboratory of Bioreactor Engineering East China University of Science and TechnologyShanghai 200237China Department of Pharmacy 302 Hospital of People’s Liberation ArmyBeijing 100039China

The asymmetric reductive amination of achiral ketones with ammonia is a particularly attractive reaction for the synthesis of chiral *** several engineered amine dehydrogenases have been developed by protein engineering for the asymmetric reductive amination of ketones,they all display(R)‐*** date,there is no report of an(S)‐stereoselective biocatalyst for this ***,a microorganism named Brevibacterium epidermidis ECU1015 that catalyzes the(S)‐selective reductive amination of ketones with ammonium has been successfully isolated from *** *** ECU1015 as the catalyst,the asymmetric reductive amination of a set of phenylacetone derivatives was successfully carried out,yielding the corresponding(S)‐chiral amines with moderate conversion and>99%enantiomeric excess.

关键词： Biocatalysis reductive amination Asymmetric synthesis Prochiral ketones Chiral amine

Catalytic reductive amination of furfural to furfurylamine on robust ultra-small Ni nanoparticles

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Nano Research 2023年第3期16卷 3719-3729页

作者： Yinze Yang Leilei Zhou Xinchao Wang Liyan Zhang Haiyang Cheng Fengyu Zhao State Key Laboratory of Electroanalytical Chemistry Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China School of Applied Chemistry and Engineering University of Science and Technology of ChinaHefei 230026China Jilin Province Key Laboratory of Green Chemistry and Process Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022China

The synthesis of primary amines via reductive amination in the presence of NH_(3)and H_(2),as a green and sustainable process,has attracted much *** this paper,we prepared series of Ni/SiO_(2)catalysts with deposition-precipitation and impregnation methods,and their catalytic performances on the reductive amination of a biomass derived compound of furfural to produce furfurylamine were *** catalytic activity and the yield were correlated to the structure and the surface properties of catalysts *** Ni/SiO_(2)is of high Lewis acidity and small Ni particle with numerous large Ni flat step surface showed high activity and selectivity,it afforded a reaction rate of 12.8 h^(−1)and a high yield to furfurylamine around 98%.These results are superior to the most non-noble metal catalysts reported so ***,the reaction route was examined with the unit control reactions of the *** produce furfurylamine selectively,the most suitable catalyst should have the moderate but not the highest activity in activation of hydrogen and hydrogenation in the reductive amination of *** work provides some useful information for the catalytic reductive amination of aldehydes both in the design of catalyst and the reaction route.

关键词： Ni nanoparticle reductive amination furfural furfurylamine

Nickel-catalyzed enantioselective reductive amination of benzylic ketones in alcohols

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Science China Chemistry 2024年第8期67卷 2566-2570页

作者： Xiuhua Wang Jianrong Steve Zhou State Key Laboratory of Chemical Oncogenomics School of Chemical Biology and BiotechnologyPeking University Shenzhen Graduate SchoolShenzhen 518055China

Asymmetric reductive amination directly converts ketones and amines to alkylamines, which are important motifs in *** report that cationic nickel complexes of chiral diphosphines promote enantioselective reductive amination of benzylic ketones with both arylamines and benzhydrazide. Isopropanol was used as a safe and cheap source of hydrogen instead of formic acid. The reaction can be readily applied to a concise synthesis of diarylethylamines, a class of neuroactive substances.

关键词： transfer hydrogenation nickel catalysis chiral alkylamine reductive amination synthetic method

A Highly Efficient Ni/Al_(2)O_(3)-LaO_(x) Catalyst for the reductive amination of Furfural to Furfurylamine:the Promoting Effect of La

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Chemical Research in Chinese Universities 2024年第1期40卷 36-46页

作者： YANG Yinze ZHANG Liyan ZHOU Leilei CHENG Haiyang ZHAO Fengyu State Key Laboratory of Electroanalytical Chemistry Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022P.R.China School of Applied Chemistry and Engineering University of Science Technology of ChinaHefei 230026P.R.China Jilin Province Key Laboratory of Green Chemistry and Process Changchun Institute of Applied ChemistryChinese Academy of SciencesChangchun 130022P.R.China

The reductive amination of furfural to furfurylamine is an important and still challenging topic in the field of biomass conversion. In this work, we prepared a series of Ni/Al_(2)O_(3)-LaO_(x) catalysts by co-precipitation method, the role of La played in promoting the catalytic performances of reductive amination furfural was discussed based on the changes in the electronic state of Ni species, acidity, and Ni particle size. The catalytic activity and the selectivity of furfurylamine are highly dependent on the surface properties and the structure of the catalyst. The addition of La promoted the amount of strong acidic sites and the H2dissociation and spillover on the surface, thus inducing the improvement of the catalytic activity and furfurylamine selectivity. The Ni/Al_(2)O_(3)-0.5LaO_(x)catalyst with suitable acid sites gave a high yield of furfurylamine (94.9%) under mild reaction conditions. Moreover, the catalyst could be recycled five times without significant loss in activity. The Ni/Al_(2)O_(3)-LaO_(x) catalyst is of great promise in the production of amines via reductive amination reaction.

关键词： reductive amination Furfural Nickel catalyst Furfurylamine Lanthanum

ZrCl_4/Hantzsch 1,4-dihydropyridine as a new and efficient reagent combination for the direct reductive amination of aldehydes and ketones with weakly basic amines

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Chinese Chemical Letters 2007年第4期18卷 458-460页

作者： Zhen Gang Liu Nan Li Li Yang Zhong Li Liu Wei Yu State Key Laboratory of Applied Organic Chemistry Lanzhou University Lanzhou 730000 China

ZrCl4/Hantzsch 1,4-dihydropyridine is a mild and highly efficient reagent combination for the direct reductive amination. Weakly basic amines such as anilines substituted by electron-withdrawing group and heteroaromatic amines can be reductively alkylated with electron rich aldehydes and ketones under mild conditions to form the secondary amines in excellent yields.

关键词： Zirconium tetractfloride Hantzsch 1,4-dihydropyfidine reductive amination