Efficient transesterification/acylation reactions mediated by N-heterocyclic carbene catalysts.

doi:10.1021/JO0267551

Paper

Efficient transesterification/acylation reactions mediated by N-heterocyclic carbene catalysts.

Published Mar 8, 2003 · G. Grasa, Tatyana Gueveli, Rohit Singh

The Journal of organic chemistry

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Abstract

Imidazol-2-ylidenes, a family of N-heterocyclic carbenes (NHC), are efficient catalysts in the transesterification involving numerous esters and alcohols. Low catalyst loadings of aryl- or alkyl-substituted NHC catalysts mediate the acylation of alcohols with enol acetates in short reaction times at room temperature. Commercially available and more difficult to cleave methyl esters react with primary alcohols in the presence of alkyl-substituted NHC to efficiently form the corresponding esters. While primary alcohols are selectively acylated over secondary alcohols with use of enol esters as acylating agents, methyl and ethyl esters can be employed as protective agents for secondary alcohols in the presence of the more active alkyl-substituted NHC catalysts. The NHC-catalyzed transesterification protocol was simplified by generating the imidazol-2-ylidene catalysts in situ.

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Imidazol-2-ylidenes efficiently catalyze transesterification and acylation reactions, enabling the use of commercially available methyl esters as protective agents for secondary alcohols.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Efficient transesterification/acylation reactions mediated by N-heterocyclic carbene catalysts.

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References

Citations

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