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Heck Reaction in Ionic Liquids and the in Situ Identification of N-Heterocyclic Carbene Complexes of Palladium
Abstract
The Heck reaction was found to proceed markedly more efficiently in the ionic liquid 1-butyl-3-methylimidazolium bromide ([bmim][Br]) than in the analogous tetrafluoroborate salt ([bmim][BF 4 ]). In relation to this observation, 1-butyl-3-methylimidazol-2-ylidene (bmiy) complexes of palladium [PdBr(μ-Br)(bmiy)] 2 ( 1 ) and [PdBr 2 (bmiy) 2 ] ( 2 ) have been isolated in [bmim][Br] but not in [bmim][BF 4 ] under conditions similar to those employed for the Heck reaction. In both the ionic liquid [bmim][Br] and molecular solvents, complex 2 was formed via the intermediate 1 . 2 has been shown to be active in the Heck reaction in [bmim][Br] but much less so in [bmim][BF 4 ] due to transformation by the latter into less active species.
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Citations
Cited by
Pârvulescu, V. I., & Hardacre, C. (2007) · Chemical Reviews · doi:10.1021/cr050948h · Cited by 2,377
Scheuermann, G. M., Rumi, L., Steurer, P., Bannwarth, W., & Mülhaupt, R. (2009) · Journal of the American Chemical Society · doi:10.1021/ja901105a · Cited by 1,163
Ionic liquids: applications in catalysis
Zhao, D., Wu, M., Kou, Y., & Min, E. (2002) · Catalysis Today · doi:10.1016/s0920-5861(01)00541-7 · Cited by 1,049
Physico-chemical processes in imidazolium ionic liquids
Dupont, J., & Suarez, P. A. Z. (2006) · Physical Chemistry Chemical Physics · doi:10.1039/b602046a · Cited by 417
Astruc, D., Lu, F., & Aranzaes, J. R. (2005) · Angewandte Chemie · doi:10.1002/ange.200500766 · Cited by 417
Metadata
- Authors
- Xu, L., Chen, W., & Xiao, J.
- Venue
- Organometallics
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-02-17
- Volume
- 19
- Issue
- 6
- Pages
- 1123-1127
- ISSN
- 0276-7333 (ISSN-L)
- 1520-6041
- OpenAlex
- W2047943849
- Cited by
- 437
- References
- 0
- FWCI
- 25.85
- Type
- journal article
- Language
- en
- Open access
- closed
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- Xu, L., Chen, W., & Xiao, J. (2000). Heck Reaction in Ionic Liquids and the in Situ Identification of N-Heterocyclic Carbene Complexes of Palladium. Organometallics. https://doi.org/10.1021/om990956m
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