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    Palladium(II), silver(I), and gold(I) complexes of a new class of chiral bicyclic [1,2,3]-triazolooxazine derived N-heterocyclic carbenes (NHCs): Synthesis, structure and application studies

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    Type
    Article
    Authors
    Gangwar, Manoj Kumar cc
    Dey, Shreyata
    Prakasham, A. P.
    Ghosh, Prasenjit
    KAUST Department
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2020-12-31
    Online Publication Date
    2020-12-31
    Print Publication Date
    2021-03
    Embargo End Date
    2022-12-31
    Submitted Date
    2020-11-05
    Permanent link to this record
    http://hdl.handle.net/10754/670180
    
    Metadata
    Show full item record
    Abstract
    A new class of chiral bicyclic [1,2,3]-triazolooxazine derived N-heterocyclic carbene (NHC) ligands was synthesised in its enantiopure form from commercially available, cheap amino acid without undertaking any chiral resolution. In particular, the bicyclic N-heterocyclic carbene precursor, (S)-7-benzyl-6,6-(R1)2–2-R2-[1,2,3]-triazolooxazinium iodide [R1 = R2 = Me (1a); R1 = H, R2 = Me (2a); R1 = H, R2 = Et (3a)] salts were conveniently prepared by the N-alkylation reactions of the corresponding [1,2,3]- triazolooxazine derivatives with alkyl iodides in ca. 37–73% yields. The copper mediated [3 + 2] cycloaddition reaction of the PhCH2CH(N3)CR2OH (R = H, Me) azido alcohol compounds and propargyl bromide gave the desired [1,2,3]-triazolooxazines. These chiral bicyclic [1,2,3]- triazolooxazine derived N-heterocyclic carbene ligands were characterised in the form of its silver (NHC)AgCl (1–3)b, gold (NHC)AuCl (1–3)c, and the palladium (NHC)2PdCl2 (1–3)d and the PEPPSI type (NHC)PdI2(NC5H5) (1–3)e complexes (NHC = (S)-7-benzyl-6,6-(R1)2–2-R2-[1,2,3]-triazolooxazin-3-ylidene; R1 = H, Me and R2 = Me, Et; PEPPSI = Pyridine Enhanced Precatalyst Preparation Stabilisation and Initiation).
    Citation
    Kumar Gangwar, M., Dey, S., A. P, P., & Ghosh, P. (2021). Palladium(II), silver(I), and gold(I) complexes of a new class of chiral bicyclic [1,2,3]-triazolooxazine derived N-heterocyclic carbenes (NHCs): Synthesis, structure and application studies. Polyhedron, 197, 115011. doi:10.1016/j.poly.2020.115011
    Sponsors
    We thank the Department of Science and Technology (Grant No: SR/S1/IC-50/2011, EMR/2014/000254, CRG/2019/000029) New Delhi, India, for financial support of this research. We gratefully acknowledge the Single Crystal X-ray Diffraction Facility, Department of Chemistry, IIT Bombay, Mumbai, India, for the crystallographic characterization data. M.K.G, A.P.P thank CSIR, New Delhi, India, and S.R.D thanks IIT Bombay, Mumbai, India for research fellowships.
    Publisher
    Elsevier BV
    Journal
    POLYHEDRON
    DOI
    10.1016/j.poly.2020.115011
    Additional Links
    https://linkinghub.elsevier.com/retrieve/pii/S0277538720306689
    Relations
    Is Supplemented By:
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1040518: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC13XR3W. DOI: 10.5517/ccdc.csd.cc13xr3w Handle: 10754/687071
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1011069: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC12Y348. DOI: 10.5517/ccdc.csd.cc12y348 Handle: 10754/687072
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1012239: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC12Z9W7. DOI: 10.5517/ccdc.csd.cc12z9w7 Handle: 10754/687073
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1024176: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC13CQY4. DOI: 10.5517/ccdc.csd.cc13cqy4 Handle: 10754/687074
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1011070: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC12Y359. DOI: 10.5517/ccdc.csd.cc12y359 Handle: 10754/687075
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1059753: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC14KRL1. DOI: 10.5517/ccdc.csd.cc14krl1 Handle: 10754/687076
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1024225: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC13CSJS. DOI: 10.5517/ccdc.csd.cc13csjs Handle: 10754/687077
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1023266: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC13BSLT. DOI: 10.5517/ccdc.csd.cc13bslt Handle: 10754/687078
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1024174: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC13CQW2. DOI: 10.5517/ccdc.csd.cc13cqw2 Handle: 10754/687079
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1012271: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC12ZBX9. DOI: 10.5517/ccdc.csd.cc12zbx9 Handle: 10754/687080
    • [Dataset]
      Gangwar, Manoj Kumar, Dey, Shreyata, P, Prakasham. A., & Ghosh, Prasenjit. (2020). CCDC 1021594: Experimental Crystal Structure Determination [Data set]. Cambridge Crystallographic Data Centre. https://doi.org/10.5517/CCDC.CSD.CC1391N3. DOI: 10.5517/ccdc.csd.cc1391n3 Handle: 10754/687081
    ae974a485f413a2113503eed53cd6c53
    10.1016/j.poly.2020.115011
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; KAUST Catalysis Center (KCC)

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