Electronic Effect of Ruthenium Nanoparticles on Efficient Reductive Amination of Carbonyl Compounds

被引:278
|
作者
Komanoya, Tasuku [1 ]
Kinemura, Takashi [1 ]
kita, Yusuke [1 ]
Kamata, Keigo [1 ]
Hara, Michikazu [1 ,2 ]
机构
[1] Tokyo Inst Technol, Inst Innovat Res, Lab Mat & Struct, Midori Ku, Nagatsuta Cho 4259, Yokohama, Kanagawa 2268503, Japan
[2] Japan Sci & Technol Agcy JST, Adv Low Carbon Technol Res & Dev Program ALCA, 4-1-8 Honcho, Kawaguchi, Saitama 3320012, Japan
基金
日本科学技术振兴机构;
关键词
NOBLE-METAL CATALYSTS; PRIMARY AMINES; SUPPORT INTERACTIONS; AMMONIA-SYNTHESIS; MOLECULAR-HYDROGEN; AQUEOUS AMMONIA; RU CATALYSTS; WATER; HYDRODECHLORINATION; TRANSFORMATION;
D O I
10.1021/jacs.7b04481
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Highly selective synthesis of primary amines over heterogeneous catalysts is still a challenge for the chemical industry. Ruthenium nanoparticles supported on Nb2O5 act as a highly selective and reusable heterogeneous catalyst for the low-temperature reductive amination of various carbonyl compounds that contain reduction-sensitive functional groups such as heterocycles and halogens with NH3 and H-2 and prevent the formation of secondary amines and undesired hydrogenated byproducts. The selective catalysis of these materials is likely attributable to the weak electron-donating capability of Ru particles on the Nb2O5 surface. The combination of this catalyst and homogeneous Ru systems was used to synthesize 2,5-bis(aminomethyl)furan, a monomer for aramid production, from 5-(hydroxymethyl)furfural without a complex mixture of imine byproducts.
引用
收藏
页码:11493 / 11499
页数:7
相关论文
共 50 条
  • [21] Selectivity tunable iron nanoparticles from lignocellulosic components for the reductive amination of carbonyl compounds towards switchable products
    Zhuang, Xiuzheng
    Wei, Xiangqian
    Hu, Xiaohong
    Zhang, Qi
    Zhang, Xinghua
    Chen, Lungang
    Liu, Jianguo
    Ma, Longlong
    GREEN CHEMISTRY, 2023, 25 (18) : 7109 - 7125
  • [22] Novel Combination of Sodium Borohydride and Reusable Polyaniline Salt Catalyst for Rapid and Efficient Reductive Amination of Carbonyl Compounds
    Devi, Chebrolu Lavanya
    Olusegun, Oladoye Sunday
    Kumar, Chebolu Naga Sesha Sai Pavan
    Rao, Vaidya Jayathirtha
    Palaniappan, Srinivasan
    CATALYSIS LETTERS, 2009, 132 (3-4) : 480 - 486
  • [23] Novel Combination of Sodium Borohydride and Reusable Polyaniline Salt Catalyst for Rapid and Efficient Reductive Amination of Carbonyl Compounds
    Chebrolu Lavanya Devi
    Oladoye Sunday Olusegun
    Chebolu Naga Sesha Sai Pavan Kumar
    Vaidya Jayathirtha Rao
    Srinivasan Palaniappan
    Catalysis Letters, 2009, 132 : 480 - 486
  • [24] Discovery of an Imine Reductase for Reductive Amination of Carbonyl Compounds with Sterically Challenging Amines
    Chen, Fei-Fei
    He, Xue-Feng
    Zhu, Xin-Xin
    Zhang, Zhi
    Shen, Xin-Yuan
    Chen, Qi
    Xu, Jian-He
    Turner, Nicholas J.
    Zheng, Gao-Wei
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (07) : 4015 - 4025
  • [25] THE REDUCTIVE AMINATION OF CARBONYL-COMPOUNDS USING SODIUM HYDROGENTELLURIDE AS A REDUCING REAGENT
    YAMASHITA, M
    KADOKURA, M
    SUEMITSU, R
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1984, 57 (11) : 3359 - 3360
  • [26] Catalytic Hydroboration and Reductive Amination of Carbonyl Compounds by HBpin using a Zinc Promoter
    Kumar, Ravi
    Rawal, Parveen
    Banerjee, Indrani
    Pada Nayek, Hari
    Gupta, Puneet
    Panda, Tarun K.
    CHEMISTRY-AN ASIAN JOURNAL, 2022, 17 (05)
  • [27] EFFICIENT REDUCTIVE ETHERIFICATION OF CARBONYL-COMPOUNDS WITH ALKOXYTRIMETHYLSILANES
    HATAKEYAMA, S
    MORI, H
    KITANO, K
    YAMADA, H
    NISHIZAWA, M
    TETRAHEDRON LETTERS, 1994, 35 (25) : 4367 - 4370
  • [28] The Reductive Amination of Carbonyl Compounds Using Native Amine Dehydrogenase from Laribacter hongkongensis
    Lee, Somin
    Jeon, Hyunwoo
    Giri, Pritam
    Lee, Uk-Jae
    Jung, Hyunsang
    Lim, Seonga
    Sarak, Sharad
    Khobragade, Taresh P.
    Kim, Byung-Gee
    Yun, Hyungdon
    BIOTECHNOLOGY AND BIOPROCESS ENGINEERING, 2021, 26 (03) : 384 - 391
  • [29] Direct reductive amination of carbonyl compounds using sodium borohydride-silica chloride
    Alinezhad, Heshmatollah
    Tajbakhsh, Mahmood
    Hamidi, Neda
    TURKISH JOURNAL OF CHEMISTRY, 2010, 34 (02) : 307 - 312
  • [30] A scrutiny on the reductive amination of carbonyl compounds catalyzed by homogeneous Rh(I) diphosphane complexes
    Tararov, VI
    Kadyrov, R
    Riermeier, TH
    Börner, A
    ADVANCED SYNTHESIS & CATALYSIS, 2002, 344 (02) : 200 - 208