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CO2 Adducts of N-Heterocyclic Carbenes: Thermal Stability and Catalytic Activity toward the Coupling of CO2 with Epoxides
Abstract
Thermal stability of CO2 adducts of N-heterocyclic carbenes (NHCs) was studied by means of in situ FTIR method with monitoring of the nu(CO2) region of the infrared spectra under various conditions. 1,3-Bis(2,6-diisopropylphenyl)imidazolinium-2-carboxylate (SIPr-CO2) shows higher thermal stability compared with 1,3-bis(2,6-diisopropylphenyl)imidazolium-2-carboxylate (IPr-CO2). The presence of free CO2 can significantly inhibit the decomposition of NHC-CO2 adducts, while the addition of an epoxide such as propylene oxide has a negative effect on stabilizing these adducts. As zwitterionic compounds, NHC-CO2 adducts were also proved to be effective organic catalysts for the coupling reaction of CO2 and epoxides to afford cyclic carbonates, for which a possible mechanism was proposed. Among these NHC-CO2 adducts, the relatively unstable IPr-CO2 exhibits the highest catalytic activity. The presence of an electrophile such as SalenAlEt could greatly improve the catalytic activity of IPr-CO2 due to intermolecular cooperative catalysis of the binary components.
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Cited by
Alves, M., Grignard, B., Mereau, R., Jerome, C., Tassaing, T., & Detrembleur, C. (2017) · Catalysis Science & Technology · doi:10.1039/c7cy00438a · Cited by 531
Green catalytic process for cyclic carbonate synthesis from carbon dioxide under mild conditions
Lang, X.-D., & He, L.-N. (2016) · The Chemical Record · doi:10.1002/tcr.201500293 · Cited by 122
Metadata
- Authors
- Zhou, H., Zhang, W.-Z., Liu, C.-H., Qu, J.-P., & Lu, X.-B.
- Venue
- The Journal of Organic Chemistry
- Publisher
- American Chemical Society (ACS)
- Published
- 2008-09-13
- Volume
- 73
- Issue
- 20
- Pages
- 8039-8044
- ISSN
- 0022-3263 (ISSN-L)
- 1520-6904
- OpenAlex
- W2044318715
- Cited by
- 364
- References
- 0
- FWCI
- 17.07
- Type
- journal article
- Language
- en
- Open access
- closed
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