Cycloaddition of CO2 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

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 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 - Dec 2017

Keywords

  • Aziridines
  • CO fixation
  • Catalysis
  • Cycloaddition of CO
  • Mechanistic study
  • Niobium

ASJC Scopus subject areas

  • Process Chemistry and Technology
  • Catalysis
  • Physical and Theoretical Chemistry

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