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

Handle URI:
http://hdl.handle.net/10754/626620
Title:
Cycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insights
Authors:
Arayachukiat, Sunatda; Yingcharoen, Prapussorn; Vummaleti, Sai V. C. ( 0000-0001-7276-2475 ) ; Cavallo, Luigi ( 0000-0002-1398-338X ) ; Poater, Albert; D’Elia, Valerio
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.
KAUST Department:
KAUST Catalysis Center (KCC)
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.
Publisher:
Elsevier BV
Journal:
Molecular Catalysis
Issue Date:
6-Nov-2017
DOI:
10.1016/j.mcat.2017.10.023
Type:
Article
ISSN:
2468-8231
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.
Additional Links:
http://www.sciencedirect.com/science/article/pii/S2468823117305679
Appears in Collections:
Articles; KAUST Catalysis Center (KCC)

Full metadata record

DC FieldValue Language
dc.contributor.authorArayachukiat, Sunatdaen
dc.contributor.authorYingcharoen, Prapussornen
dc.contributor.authorVummaleti, Sai V. C.en
dc.contributor.authorCavallo, Luigien
dc.contributor.authorPoater, Alberten
dc.contributor.authorD’Elia, Valerioen
dc.date.accessioned2018-01-01T12:19:03Z-
dc.date.available2018-01-01T12:19:03Z-
dc.date.issued2017-11-06en
dc.identifier.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.en
dc.identifier.issn2468-8231en
dc.identifier.doi10.1016/j.mcat.2017.10.023en
dc.identifier.urihttp://hdl.handle.net/10754/626620-
dc.description.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.en
dc.description.sponsorshipA.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.en
dc.publisherElsevier BVen
dc.relation.urlhttp://www.sciencedirect.com/science/article/pii/S2468823117305679en
dc.subjectAziridinesen
dc.subjectNiobiumen
dc.subjectCO2 fixationen
dc.subjectCatalysisen
dc.subjectCycloaddition of CO2en
dc.subjectMechanistic studyen
dc.titleCycloaddition of CO 2 to challenging N -tosyl aziridines using a halogen-free niobium complex: Catalytic activity and mechanistic insightsen
dc.typeArticleen
dc.contributor.departmentKAUST Catalysis Center (KCC)en
dc.identifier.journalMolecular Catalysisen
dc.contributor.institutionDepartment of Materials Science and Engineering, School of Molecular Science and Engineering, Vidyasirimedhi Institute of Science and Technology (VISTEC), 21210, Wang Chan, Thailanden
dc.contributor.institutionInstitut de Química Computacional i Catàlisi and Departament de Química, Universitat de Girona, c/Maria Aurèlia Capmany 6, 17003 Girona, Catalonia, Spainen
kaust.authorVummaleti, Sai V. C.en
kaust.authorCavallo, Luigien
All Items in KAUST are protected by copyright, with all rights reserved, unless otherwise indicated.