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Liquid-Phase Hydrogenation of Nitriles to Amines Facilitated by a Co(II)/Zn(0) Pair: A Ligand-Free Catalytic Protocol

  • Daniel Timelthaler
    Daniel Timelthaler
    Institute of Catalysis (INCA), Johannes Kepler University (JKU), 4040 Linz, Austria
  •  and 
  • Christoph Topf*
    Christoph Topf
    Institute of Catalysis (INCA), Johannes Kepler University (JKU), 4040 Linz, Austria
    *E-mail: [email protected]
Cite this: J. Org. Chem. 2019, 84, 18, 11604–11611
Publication Date (Web):August 27, 2019
https://doi.org/10.1021/acs.joc.9b01544
Copyright © 2019 American Chemical Society

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    Abstract

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    The given report introduces a simple and user-friendly in situ method for the production of catalytically active cobalt particles. The approach circumvents the use of air- and moisture-sensitive reductants as well as the application of anhydrous Co-precursor salts. Accordingly, the described catalytic system is readily assembled under open-flask conditions by simply combining the components in the reaction vessel. Therefore, the arduous charging procedure of the reaction autoclave in a glovebox under an inert gas atmosphere is no longer necessary. In fact, the catalytically active material is obtained upon treatment of readily available Co(OAc)2·4 H2O with benign commercial Zn powder. The catalytic performance of the resultant material was tested in the heterogeneous hydrogenation of nitriles to the corresponding primary amines. Both activity and selectivity of the cobalt catalyst are significantly enhanced if a triflate-based Lewis acid and ammonia is added to the reaction mixture.

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    The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acs.joc.9b01544.

    • Elucidation of the effect of different solvents on the catalyst performance; description of the influence of various Co precursors, reaction temperature, and H2 pressure on the catalytic activity; study of the aptitude of selected metals and metalloids to function as reducing agents; and 1H-NMR, 13C{1H}-NMR, 19F-NMR, and HR-MS spectra of the isolated products (PDF)

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    Cited By

    This article is cited by 11 publications.

    1. Hao Song, Yao Xiao, Zhuohua Zhang, Wanjin Xiong, Ren Wang, Liangcheng Guo, Taigang Zhou. Switching Selectivity in Copper-Catalyzed Transfer Hydrogenation of Nitriles to Primary Amine-Boranes and Secondary Amines under Mild Conditions. The Journal of Organic Chemistry 2022, 87 (1) , 790-800. https://doi.org/10.1021/acs.joc.1c02413
    2. Gabriella Amberchan, Rachel A. Snelling, Enrique Moya, Madison Landi, Kyle Lutz, Roxanne Gatihi, Bakthan Singaram. Reaction of Diisobutylaluminum Borohydride, a Binary Hydride, with Selected Organic Compounds Containing Representative Functional Groups. The Journal of Organic Chemistry 2021, 86 (9) , 6207-6227. https://doi.org/10.1021/acs.joc.0c03062
    3. Suman Das, Jyotirmoy Maity, Tarun K. Panda. Metal/Non‐Metal Catalyzed Activation of Organic Nitriles. The Chemical Record 2022, 22 (12) https://doi.org/10.1002/tcr.202200192
    4. Adwitiya Pal, Arunabha Thakur. One-pot synthesis of dimerized arenes and heteroarenes under mild conditions using Co( i ) as an active catalyst. Organic & Biomolecular Chemistry 2022, 20 (45) , 8977-8987. https://doi.org/10.1039/D2OB01738E
    5. Kahoko Kato, Dian Deng, Yusuke Kita, Keigo Kamata, Michikazu Hara. Primary amine synthesis by hydrogen-involving reactions over heterogeneous cobalt catalysts. Catalysis Science & Technology 2022, 12 (17) , 5425-5434. https://doi.org/10.1039/D2CY00870J
    6. Daniel Timelthaler, Christoph Topf. Heterogeneous Hydrogenation of Quinoline Derivatives Effected by a Granular Cobalt Catalyst. Synthesis 2022, 54 (03) , 629-642. https://doi.org/10.1055/a-1654-3302
    7. Qiqi Lu, Jianguo Liu, Longlong Ma. Recent advances in selective catalytic hydrogenation of nitriles to primary amines. Journal of Catalysis 2021, 404 , 475-492. https://doi.org/10.1016/j.jcat.2021.10.028
    8. Chuhan Li, Shuo Song, Yuling Li, Chang Xu, Qiquan Luo, Yinlong Guo, Xiaoming Wang. Selective hydroboration of unsaturated bonds by an easily accessible heterotopic cobalt catalyst. Nature Communications 2021, 12 (1) https://doi.org/10.1038/s41467-021-24117-5
    9. Vincent Vermaak, Hermanus C.M. Vosloo, Andrew J. Swarts. Chemoselective transfer hydrogenation of nitriles to secondary amines with nickel(II) catalysts. Molecular Catalysis 2021, 511 , 111738. https://doi.org/10.1016/j.mcat.2021.111738
    10. Daniel Timelthaler, Wolfgang Schöfberger, Christoph Topf. Selective and Additive‐Free Hydrogenation of Nitroarenes Mediated by a DMSO‐Tagged Molecular Cobalt Corrole Catalyst. European Journal of Organic Chemistry 2021, 2021 (14) , 2114-2120. https://doi.org/10.1002/ejoc.202100073
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