Aerobic Activation of C-H Bond in Amines Over a Nanorod Manganese Oxide Catalyst

被引:19
作者
Wang, Hai [1 ]
Wang, Liang [1 ]
Wang, Sai [1 ]
Dong, Xue [2 ]
Zhang, Jian [1 ,3 ]
Xiao, Feng-Shou [1 ,3 ]
机构
[1] Zhejiang Univ, Dept Chem, Key Lab Appl Chem Zhejiang Prov, Hangzhou 310028, Zhejiang, Peoples R China
[2] Texas Tech Univ, Dept Chem & Biochem, Lubbock, TX 79409 USA
[3] Beijing Univ Chem Technol, Beijing Adv Innovat Ctr Soft Matter Sci & Engn, Beijing 100029, Peoples R China
基金
中国国家自然科学基金;
关键词
amine oxidation; manganese oxide; nanorod catalyst; amide; SELECTIVE OXIDATION; NANOPARTICLES; DIOXYGEN; HYDROCARBONS; OXYGENATION; BIOMASS; AMIDES; FUELS;
D O I
10.1002/cctc.201801058
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The development of heterogeneous catalysts for the synthesis of pharmaceutically relevant compounds is always important for chemistry research. Here, we report a selective aerobic oxidation of aromatic and aliphatic amines to corresponding amides over a nanorod manganese oxide (NR-MnOx) catalyst. The kinetic studies reveal that the NR-MnOx catalyzed amine-to-amide reaction proceeds the oxidative dehydrogenation of the amines into nitriles, followed by hydrolysis of nitrile into amides. The NR-MnOx exhibits fast kinetics and high selectivities in these steps, as well as hinders the by-product formation. More importantly, the NR-MnOx catalyst is stable and reusable in the continuous recycle tests with water as a sole by-product, exhibiting superior sustainability and significant advancement to outperform the traditional amide production route in acidic or basic media with toxic by-products.
引用
收藏
页码:401 / 406
页数:6
相关论文
共 34 条
  • [1] [Anonymous], 2008, ANGEW CHEM INT EDIT, DOI DOI 10.1002/ANGE.200802464
  • [2] A multitasking functional group leads to structural diversity using designer C-H activation reaction cascades
    Chen, Ying
    Wang, Dongqi
    Duan, Pingping
    Ben, Rong
    Dai, Lu
    Shao, Xiaoru
    Hong, Mei
    Zhao, Jing
    Huang, Yong
    [J]. NATURE COMMUNICATIONS, 2014, 5
  • [3] Chheda J.N., 2007, Angew. Chem, V119, P7298
  • [4] Liquid-phase catalytic processing of biomass-derived oxygenated hydrocarbons to fuels and chemicals
    Chheda, Juben N.
    Huber, George W.
    Dumesic, James A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (38) : 7164 - 7183
  • [5] Molecular recognition in the selective oxygenation of saturated C-H bonds by a dimanganese catalyst
    Das, Siddhartha
    Incarvito, Christopher D.
    Crabtree, Robert H.
    Brudvig, Gary W.
    [J]. SCIENCE, 2006, 312 (5782) : 1941 - 1943
  • [6] Selective hydrocarbon oxidation in zeolites
    Frei, Heinz
    [J]. SCIENCE, 2006, 313 (5785) : 309 - 310
  • [7] Fujiwara H., 2007, ANGEW CHEM, V119, P5294
  • [8] MOF-derived cobalt nanoparticles catalyze a general synthesis of amines
    Jagadeesh, Rajenahally V.
    Murugesan, Kathiravan
    Alshammari, Ahmad S.
    Neumann, Helfried
    Pohl, Marga-Martina
    Radnik, Joerg
    Beller, Matthias
    [J]. SCIENCE, 2017, 358 (6361) : 326 - +
  • [9] Solvent-Free Oxidation of Primary Carbon-Hydrogen Bonds in Toluene Using Au-Pd Alloy Nanoparticles
    Kesavan, Lokesh
    Tiruvalam, Ramchandra
    Ab Rahim, Mohd Hasbi
    bin Saiman, Mohd Izham
    Enache, Dan I.
    Jenkins, Robert L.
    Dimitratos, Nikolaos
    Lopez-Sanchez, Jose A.
    Taylor, Stuart H.
    Knight, David W.
    Kiely, Christopher J.
    Hutchings, Graham J.
    [J]. SCIENCE, 2011, 331 (6014) : 195 - 199
  • [10] Heterogeneously Catalyzed Efficient Oxygenation of Primary Amines to Amides by a Supported Ruthenium Hydroxide Catalyst
    Kim, Jung Won
    Yamaguchi, Kazuya
    Mizuno, Noritaka
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (48) : 9249 - 9251