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

Sunatda Arayachukiat, Prapussorn Yingcharoen, Sai V. C. Vummaleti, Luigi Cavallo, Albert Poater, Valerio D’Elia

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.
Original languageEnglish (US)
Pages (from-to)280-285
Number of pages6
JournalMolecular Catalysis
Volume443
DOIs
StatePublished - Nov 6 2017

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