Cycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights
Type
ArticleAuthors
Arayachukiat, SunatdaYingcharoen, Prapussorn
Vummaleti, Sai V. C.

Cavallo, Luigi

Poater, Albert

D’Elia, Valerio

KAUST Department
Chemical Science ProgramKAUST Catalysis Center (KCC)
Physical Science and Engineering (PSE) Division
Date
2017-11-06Online Publication Date
2017-11-06Print Publication Date
2017-12Permanent link to this record
http://hdl.handle.net/10754/626620
Metadata
Show full item recordAbstract
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 BVJournal
Molecular CatalysisAdditional Links
http://www.sciencedirect.com/science/article/pii/S2468823117305679ae974a485f413a2113503eed53cd6c53
10.1016/j.mcat.2017.10.023