Intramolecular frustrated N/B lewis pairs by enamine hydroboration

被引:131
|
作者
Schwendemann, Sina [1 ]
Froehlich, Roland [1 ]
Kehr, Gerald [1 ]
Erker, Gerhard [1 ]
机构
[1] Univ Munster, Inst Organ Chem, D-48149 Munster, Germany
关键词
FREE CATALYTIC-HYDROGENATION; HETEROLYTIC DIHYDROGEN ACTIVATION; METAL-FREE; ADDITION-REACTIONS; BOND ACTIVATION; ACID; REACTIVITY; H-2; MECHANISM; IMINES;
D O I
10.1039/c1sc00124h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of enamines undergoes anti-Markovnikov hydroboration with Piers' borane HB(C6F5)(2) to yield C-2-bridged frustrated N/B Lewis pairs, featuring weak N center dot center dot center dot B interaction. Some examples show typical frustrated Lewis pair reactions with dihydrogen or with 1-alkynes. One such N/B FLP serves as an active catalyst for the hydrogenation of enamines. Many of the new compounds were characterized by X-ray diffraction.
引用
收藏
页码:1842 / 1849
页数:8
相关论文
共 50 条
  • [1] The activity and reversibility of intramolecular B/N Frustrated Lewis Pairs in the hydrogenation
    Mao, Hui
    Chen, Zijiang
    Cheng, Longjiu
    Wang, Kun
    INTERNATIONAL JOURNAL OF HYDROGEN ENERGY, 2021, 46 (01) : 110 - 118
  • [2] Intramolecular B/N frustrated Lewis pairs and the hydrogenation of carbon dioxide
    Courtemanche, Marc-Andre
    Pulis, Alexander P.
    Rochette, Etienne
    Legare, Marc-Andre
    Stephan, Douglas W.
    Fontaine, Frederic-Georges
    CHEMICAL COMMUNICATIONS, 2015, 51 (48) : 9797 - 9800
  • [3] Enantioselective hydroboration with chiral frustrated Lewis pairs
    Ghattas, Ghazi
    Klankermayer, Juergen
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [4] Intramolecular cooperativity in frustrated Lewis pairs
    Koerte, Leif A.
    Blomeyer, Sebastian
    Heidemeyer, Shari
    Mix, Andreas
    Neumann, Beate
    Mitzel, Norbert W.
    CHEMICAL COMMUNICATIONS, 2016, 52 (64) : 9949 - 9952
  • [5] Insight into acrolein activation by P/B intramolecular frustrated Lewis pairs
    Sinha, Swapan
    Das, Subhra
    Giri, Santanab
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2024, 37 (02)
  • [6] Intramolecular frustrated Lewis pairs: Some recent developments
    Erker, Gerhard
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [7] Intramolecular Frustrated Lewis Pairs: Formation and Chemical Features
    Kehr, Gerald
    Schwendemann, Sina
    Erker, Gerhard
    FRUSTRATED LEWIS PAIRS I: UNCOVERING AND UNDERSTANDING, 2013, 332 : 45 - 83
  • [8] Implications of CO2 Activation by Frustrated Lewis Pairs in the Catalytic Hydroboration of CO2: A View Using N/Si+ Frustrated Lewis Pairs
    von Wolff, N.
    Lefevre, G.
    Berthet, J. -C.
    Thuery, P.
    Cantat, T.
    ACS CATALYSIS, 2016, 6 (07): : 4526 - 4535
  • [9] Computational studies of catalytic hydrogenation with intramolecular frustrated Lewis pairs
    Ginovska-Pangovska, Bojana
    Camaioni, Donald
    Autrey, Thomas
    Schenter, Gregory
    Kathmann, Shawn
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 248
  • [10] Intramolecular pyridine-based frustrated Lewis-pairs
    Koerte, Leif A.
    Warner, Robin
    Vishnevskiy, Yury V.
    Neumann, Beate
    Stammler, Hans-Georg
    Mitzel, Norbert W.
    DALTON TRANSACTIONS, 2015, 44 (21) : 9992 - 10002