Catalytic Methylation of C-H Bonds Using CO2 and H2

被引:102
作者
Li, Yuehui [1 ]
Yan, Tao [1 ]
Junge, Kathrin [1 ]
Beller, Matthias [1 ]
机构
[1] Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
关键词
carbon dioxide; C-H activation; heterocycles; hydrogen; ruthenium; CARBON-DIOXIDE; DIRECT CARBOXYLATION; IRIDIUM CATALYST; REDUCTION; HYDROGENATION; METHANOL; ESTERS; ACID; DERIVATIVES; LIGANDS;
D O I
10.1002/anie.201405779
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Formation of C-C bonds from CO2 is a much sought after reaction in organic synthesis. To date, other than C-H carboxylations using stoichiometric amounts of metals, base, or organometallic reagents, little is known about C-C bond formation. In fact, to the best of our knowledge no catalytic methylation of C-H bonds using CO2 and H-2 has been reported. Described herein is the combination of CO2 and H-2 for efficient methylation of carbon nucleophiles such as indoles, pyrroles, and electron-rich arenes. Comparison experiments which employ paraformaldehyde show similar reactivity for the CO2/H-2 system.
引用
收藏
页码:10476 / 10480
页数:5
相关论文
共 66 条
  • [21] Homogeneous Catalytic Hydrogenation of Amides to Amines
    Coetzee, Jacorien
    Dodds, Deborah L.
    Klankermayer, Juergen
    Brosinski, Sandra
    Leitner, Walter
    Slawin, Alexandra M. Z.
    Cole-Hamilton, David J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (33) : 11039 - 11050
  • [22] CORREA A, 2009, ANGEW CHEM, V121, P6317, DOI DOI 10.1002/ANGE.200900667
  • [23] Metal-Catalyzed Carboxylation of Organometallic Reagents with Carbon Dioxide
    Correa, Arkaitz
    Martin, Ruben
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (34) : 6201 - 6204
  • [24] A Well-Defined Iron Catalyst for the Reduction of Bicarbonates and Carbon Dioxide to Formates, Alkyl Formates, and Formamides
    Federsel, Christopher
    Boddien, Albert
    Jackstell, Ralf
    Jennerjahn, Reiko
    Dyson, Paul J.
    Scopelliti, Rosario
    Laurenczy, Gabor
    Beller, Matthias
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (50) : 9777 - 9780
  • [25] Selective Homogeneous Hydrogenation of Biogenic Carboxylic Acids with [Ru(TriPhos)H]+: A Mechanistic Study
    Geilen, Frank M. A.
    Engendahl, Barthel
    Hoelscher, Markus
    Klankermayer, Juergen
    Leitner, Walter
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (36) : 14349 - 14358
  • [26] Selective and Flexible Transformation of Biomass-Derived Platform Chemicals by a Multifunctional Catalytic System
    Geilen, Frank M. A.
    Engendahl, Barthel
    Harwardt, Andreas
    Marquardt, Wolfgang
    Klankermayer, Juergen
    Leitner, Walter
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (32) : 5510 - 5514
  • [27] HAN Z, 2012, ANGEW CHEM, V124, P13218, DOI DOI 10.1002/ANGE.201207781
  • [28] Catalytic Hydrogenation of Cyclic Carbonates: A Practical Approach from CO2 and Epoxides to Methanol and Diols
    Han, Zhaobin
    Rong, Liangce
    Wu, Jiang
    Zhang, Lei
    Wang, Zheng
    Ding, Kuiling
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (52) : 13041 - 13045
  • [29] Transition-metal-catalyzed C-C bond formation through the fixation of carbon dioxide
    Huang, Kun
    Sun, Chang-Liang
    Shi, Zhang-Jie
    [J]. CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) : 2435 - 2452
  • [30] Hull JF, 2012, NAT CHEM, V4, P383, DOI [10.1038/nchem.1295, 10.1038/NCHEM.1295]