N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions

G A Grasa, R M Kissling, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

324 Citations (Scopus)

Abstract

[GRAPHICS]

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.

Original languageEnglish
Pages (from-to)3583-3586
Number of pages4
JournalOrganic Letters
Volume4
Issue number21
DOIs
Publication statusPublished - 17 Oct 2002

Keywords

  • HIGHLY SELECTIVE ACYLATION
  • ALCOHOLS
  • ANHYDRIDES
  • TRIFLUOROMETHANESULFONATE
  • ESTERS
  • ACID

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