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    MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts

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    Type
    Article
    Authors
    Davaasuren, Bambar cc
    Emwas, Abdul-Hamid M.
    Rothenberger, Alexander
    KAUST Department
    Chemical Science Program
    Imaging and Characterization Core Lab
    NMR
    Physical Science and Engineering (PSE) Division
    Date
    2017-08-08
    Online Publication Date
    2017-08-08
    Print Publication Date
    2017-08-21
    Permanent link to this record
    http://hdl.handle.net/10754/625726
    
    Metadata
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    Abstract
    High surface area macroporous chalcogenide aerogels (chalcogels) MAu2GeS4 (M = Co, Ni) were prepared from K2Au2GeS4 precursor and Co(OAc)2 or NiCl2 by one-pot sol-gel metathesis reactions in aqueous media. The MAu2GeS4-chalcogels were screened for catalytic intramolecular hydroamination of 4-pentyn-1-amine substrate at different temperatures. 87% and 58% conversion was achieved at 100 °C, using CoAu2GeS4- and NiAu2GeS4-chalcogels respectively, and the reaction kinetics follows the first order. It was established that the catalytic performance of the aerogels is associated with the M(2+) centers present in the structure. Intermolecular hydroamination of aniline with 1-R-4-ethynylbenzene (R = -H, -OCH3, -Br, -F) was carried out at 100 °C using CoAu2GeS4-chalcogel catalyst, due to its promising catalytic performance. The CoAu2GeS4-chalcogel regioselectively converted the pair of substrates to respective Markovnikov products, (E)-1-(4-R-phenyl)-N-phenylethan-1-imine, with 38% to 60% conversion.
    Citation
    Davaasuren B, Emwas A-H, Rothenberger A (2017) MAu2GeS4-Chalcogel (M = Co, Ni): Heterogeneous Intra- and Intermolecular Hydroamination Catalysts. Inorganic Chemistry 56: 9609–9616. Available: http://dx.doi.org/10.1021/acs.inorgchem.7b01099.
    Sponsors
    This research was supported by King Abdullah University of Science and Technology (KAUST) baseline funding. We would like to thank Prof. P. W. Roesky for the advice in catalytic activity measurement and Dr. E. Ahmed for the assistance in chalcogel preparation.
    Publisher
    American Chemical Society (ACS)
    Journal
    Inorganic Chemistry
    DOI
    10.1021/acs.inorgchem.7b01099
    PubMed ID
    28787154
    Additional Links
    http://pubs.acs.org/doi/abs/10.1021/acs.inorgchem.7b01099
    Relations
    Is Supplemented By:
    • [Dataset]
      . DOI: 10.5517/ccdc.csd.cc1nxc86 HANDLE: 10754/663842
    ae974a485f413a2113503eed53cd6c53
    10.1021/acs.inorgchem.7b01099
    Scopus Count
    Collections
    Articles; Imaging and Characterization Core Lab; Physical Science and Engineering (PSE) Division; Chemical Science Program

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