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N-Heterocyclic Carbenes as Versatile Nucleophilic Catalysts for Transesterification/Acylation Reactions

Organic Letters · 2002 · Vol. 4(21) · pp. 3583–3586

Gabriela A. Grasa✉(University of New Orleans)Rebecca M. Kissling(University of New Orleans)Steven P. Nolan(University of New Orleans)

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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.

Chemical Synthesis and Reactions N-Heterocyclic Carbenes in Organic and Inorganic Chemistry Catalytic Cross-Coupling ReactionsChemistryCatalysisTransesterificationAcylationNucleophileAlkylOrganic chemistryArylMedicinal chemistryCombinatorial chemistry

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