Cycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights
Vummaleti, Sai V. C.
KAUST DepartmentChemical Science Program
KAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Online Publication Date2017-11-06
Print Publication Date2017-12
Permanent link to this recordhttp://hdl.handle.net/10754/626620
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AbstractAn 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.
CitationArayachukiat 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.
SponsorsA.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.