A halogen-bonding-catalyzed Michael addition reaction

被引：113
作者：
Gliese, Jan-Philipp [1 ]
Jungbauer, Stefan H. [1 ]
Huber, Stefan M. [1 ]
机构：
[1] Ruhr Univ Bochum, Dept Chem & Biochem, Univ Str 150, D-44801 Bochum, Germany
来源：
CHEMICAL COMMUNICATIONS | 2017年 / 53卷 / 88期
基金：
欧洲研究理事会;
关键词：
BASIS-SETS; ORGANOCATALYSIS; DONORS;
D O I：
10.1039/c7cc07175b
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Only a few studies on the use of halogen bonding in catalysis have been published so far. Herein, (benz) imidazolium-based halogen bond donors are used as catalysts in a Michael addition reaction. The most potent catalyst, a rigid atropisomer featuring two iodo-benzimidazolium moieties, provided a rate acceleration versus a reference compound of ca. 50.
引用
收藏
页码：12052 / 12055
页数：4
相关论文
共 25 条
  • [1] Halogen bonding in solution: thermodynamics and applications
    Beale, Thomas M.
    Chudzinski, Michael G.
    Sarwar, Mohammed G.
    Taylor, Mark S.
    [J]. CHEMICAL SOCIETY REVIEWS, 2013, 42 (04) : 1667 - 1680
  • [2] Combining metals with halogen bonds
    Brammer, Lee
    Espallargas, Guillermo Minguez
    Libri, Stefano
    [J]. CRYSTENGCOMM, 2008, 10 (12): : 1712 - 1727
  • [3] Organocatalysis through halogen-bond activation
    Bruckmann, Angelika
    Pena, Miguel A.
    Bolm, Carsten
    [J]. SYNLETT, 2008, (06) : 900 - 902
  • [4] Halogen Bonding in Organic Synthesis and Organocatalysis
    Bulfield, David
    Huber, Stefan M.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (41) : 14434 - 14450
  • [5] The Halogen Bond
    Cavallo, Gabriella
    Metrangolo, Pierangelo
    Milani, Roberto
    Pilati, Tullio
    Priimagi, Arri
    Resnati, Giuseppe
    Terraneo, Giancarlo
    [J]. CHEMICAL REVIEWS, 2016, 116 (04) : 2478 - 2601
  • [6] Halogen bonding in solution
    Erdelyi, Mate
    [J]. CHEMICAL SOCIETY REVIEWS, 2012, 41 (09) : 3547 - 3557
  • [7] A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu
    Grimme, Stefan
    Antony, Jens
    Ehrlich, Stephan
    Krieg, Helge
    [J]. JOURNAL OF CHEMICAL PHYSICS, 2010, 132 (15)
  • [8] Cationic Multidentate Halogen-Bond Donors in Halide Abstraction Organocatalysis: Catalyst Optimization by Preorganization
    Jungbauer, Stefan H.
    Huber, Stefan M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (37) : 12110 - 12120
  • [9] Activation of a carbonyl compound by halogen bonding
    Jungbauer, Stefan H.
    Walter, Sebastian M.
    Schindler, Severin
    Rout, Laxmidhar
    Kniep, Florian
    Huber, Stefan M.
    [J]. CHEMICAL COMMUNICATIONS, 2014, 50 (47) : 6281 - 6284
  • [10] Organocatalysis by Neutral Multidentate Halogen-Bond Donors
    Kniep, Florian
    Jungbauer, Stefan H.
    Zhang, Qi
    Walter, Sebastian M.
    Schindler, Severin
    Schnapperelle, Ingo
    Herdtweck, Eberhardt
    Huber, Stefan M.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (27) : 7028 - 7032
123