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N-Heterocyclic Carbenes as Versatile Nucleophilic Catalysts for Transesterification/Acylation Reactions
Abstract
[reaction: see text] Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification between esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with vinyl acetate in convenient reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with numerous alcohols in the presence of alkyl-substituted NHC to form efficiently the corresponding esters in very short reaction times.
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Cited by
Controlled Ring-Opening Polymerization of Lactide and Glycolide
Dechy-Cabaret, O., Martin-Vaca, B., & Bourissou, D. (2004) · Chemical Reviews · doi:10.1021/cr040002s · Cited by 2,257
Organocatalytic Ring-Opening Polymerization
Kamber, N. E., Jeong, W., Waymouth, R. M., Pratt, R. C., Lohmeijer, B. G. G., & Hedrick, J. L. (2007) · Chemical Reviews · doi:10.1021/cr068415b · Cited by 1,489
Organocatalysis: Opportunities and Challenges for Polymer Synthesis
Kiesewetter, M. K., Shin, E. J., Hedrick, J. L., & Waymouth, R. M. (2010) · Macromolecules · doi:10.1021/ma9025948 · Cited by 907
Progress in Catalytic Ring-Opening Polymerization of Biobased Lactones
Al-Shok, L., Haddleton, D. M., & Adams, F. (2022) · Advances in Polymer Science · doi:10.1007/12_2021_111 · Cited by 10
Metadata
- Authors
- Grasa, G. A., Kissling, R. M., & Nolan, S. P.
- Venue
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Published
- 2002-09-25
- Volume
- 4
- Issue
- 21
- Pages
- 3583-3586
- ISSN
- 1523-7052 (ISSN-L)
- 1523-7060
- OpenAlex
- W2134901576
- Cited by
- 355
- References
- 0
- FWCI
- 10.76
- Type
- journal article
- Language
- en
- Open access
- closed
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- Grasa, G. A., Kissling, R. M., & Nolan, S. P. (2002). N-Heterocyclic Carbenes as Versatile Nucleophilic Catalysts for Transesterification/Acylation Reactions. Organic Letters. https://doi.org/10.1021/ol0264760
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