Microwave-assisted FLP-catalyzed hydrogenations

被引:14
|
作者
Tussing, S. [1 ]
Paradies, J. [1 ]
机构
[1] Univ Paderborn, Inst Organ Chem, Warburger Str 100, D-33098 Paderborn, Germany
关键词
FRUSTRATED LEWIS PAIRS; HETEROLYTIC DIHYDROGEN ACTIVATION; METAL-FREE HYDROGENATION; ENANTIOSELECTIVE HYDROGENATION; ASYMMETRIC HYDROGENATION; IMINES; REDUCTION;
D O I
10.1039/c5dt03857j
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
FLP-catalyzed hydrogenations of 15 substrates were compared using microwave irradiation and conventional heating. The direct comparison revealed that a rate acceleration of up to 2.5 was achieved in the presence of microwaves. This heating method is particularly promising for the hydrogenation of nitrogen-containing heterocycles. Acridine, quinines and especially 1-methyl indole were reduced very efficiently under mild conditions and only 4 bar hydrogen pressure in high yields.
引用
收藏
页码:6124 / 6128
页数:5
相关论文
共 50 条
  • [2] Mechanistic Insights into FLP-Catalyzed Iodoperfluoroalkylations
    Spittler, Michael
    Helmecke, Lucas
    Czekelius, Constantin
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 2019 (2-3) : 458 - 468
  • [3] FLP-Catalyzed Transfer Hydrogenation of Silyl Enol Ethers
    Khan, Imtiaz
    Reed-Berendt, Benjamin G.
    Melen, Rebecca L.
    Morrill, Louis C.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (38) : 12356 - 12359
  • [4] Microwave-assisted hydrogenations using frustrated Lewis pairs
    Miao, Yilan
    Robertson, Luke
    Valentin, Elizabeth
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2018, 255
  • [5] Origin of Stereoselectivity in FLP-Catalyzed Asymmetric Hydrogenation of Imines
    Hamza, Andrea
    Sorochkina, Kristina
    Kotai, Bianka
    Chernichenko, Konstantin
    Berta, Denes
    Bolte, Michael
    Nieger, Martin
    Repo, Timo
    Papai, Imre
    ACS CATALYSIS, 2020, 10 (23): : 14290 - 14301
  • [6] Stereocontrol via Propeller Chirality in FLP-Catalyzed Asymmetric Hydrogenation
    Kotai, B.
    Laczko, G.
    Hamza, A.
    Papai, I.
    CHEMISTRY-A EUROPEAN JOURNAL, 2024, 30 (21)
  • [7] Chiral FLP-catalyzed asymmetric hydrogenation of 3-fluorinated chromones
    Dai, Yun
    Meng, Wei
    Feng, Xiangqing
    Du, Haifeng
    CHEMICAL COMMUNICATIONS, 2022, 58 (10) : 1558 - 1560
  • [8] Microwave-Assisted Ruthenium-Catalyzed Reactions
    Nicks, Francois
    Borguet, Yannick
    Delfosse, Sebastien
    Bicchielli, Dario
    Delaude, Lionel
    Sauvage, Xavier
    Demonceau, Albert
    AUSTRALIAN JOURNAL OF CHEMISTRY, 2009, 62 (03) : 184 - 207
  • [9] FLP-Catalyzed Monoselective C-F Functionalization in Polyfluorocarbons at Geminal or Distal Sites
    Gupta, Richa
    Mandal, Dipendu
    Jaiswal, Amit K.
    Young, Rowan D.
    ORGANIC LETTERS, 2021, 23 (05) : 1915 - 1920
  • [10] Microwave-assisted and metal-catalyzed coupling reactions
    Nilsson, P.
    Ofsson, K.
    Larhed, M.
    MICROWAVE METHODS IN ORGANIC SYNTHESIS, 2006, 266 : 103 - 144