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    Cycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights

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    Type
    Article
    Authors
    Arayachukiat, Sunatda
    Yingcharoen, Prapussorn
    Vummaleti, Sai V. C. cc
    Cavallo, Luigi cc
    Poater, Albert cc
    D’Elia, Valerio cc
    KAUST Department
    Chemical Science Program
    KAUST Catalysis Center (KCC)
    Physical Science and Engineering (PSE) Division
    Date
    2017-11-06
    Online Publication Date
    2017-11-06
    Print Publication Date
    2017-12
    Permanent link to this record
    http://hdl.handle.net/10754/626620
    
    Metadata
    Show full item record
    Abstract
    An efficient and facile approach to the regioselective synthesis of N-tosyloxazolidinones from the corresponding N-tosylaziridines and CO2 was developed using dual catalytic systems involving an early transition metal coordination compound as a Lewis acid and a nucleophilic cocatalyst. Among the screened Lewis acids, halogen-free niobium pentaethoxide (Nb(OEt)5) displayed the best catalytic activity when used in the presence of tetrabutylammonium iodide (TBAI). Systematic DFT calculations, supported by catalytic experiments, demonstrate that CO2 insertion is the rate determining step for this process and it is highly dependent on the steric hindrance at the niobium center.
    Citation
    Arayachukiat S, Yingcharoen P, Vummaleti SVC, Cavallo L, Poater A, et al. (2017) Cycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights. Molecular Catalysis 443: 280–285. Available: http://dx.doi.org/10.1016/j.mcat.2017.10.023.
    Sponsors
    A.P. thanks the Spanish MINECO for a project CTQ2014-59832-JIN, and EU for a FEDER fund (UNGI08-4E-003). V.D.E. thanks the Thailand Research Fund (Grant No. RSA6080059) for funding this research. S.A. acknowledges financial support through postdoctoral fellowship from the Vidyasirimedhi Institute of Science and Technology.
    Publisher
    Elsevier BV
    Journal
    Molecular Catalysis
    DOI
    10.1016/j.mcat.2017.10.023
    Additional Links
    http://www.sciencedirect.com/science/article/pii/S2468823117305679
    ae974a485f413a2113503eed53cd6c53
    10.1016/j.mcat.2017.10.023
    Scopus Count
    Collections
    Articles; Physical Science and Engineering (PSE) Division; Chemical Science Program; KAUST Catalysis Center (KCC)

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