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

G A Grasa, T Guveli, R Singh, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

217 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)2812-2819
Number of pages8
JournalThe Journal of Organic Chemistry
Volume68
Issue number7
DOIs
Publication statusPublished - 4 Apr 2003

Keywords

  • PALLADIUM/IMIDAZOLIUM SALT SYSTEMS
  • QUATERNARY AMMONIUM SALT
  • CROSS-COUPLING REACTIONS
  • ASYMMETRIC EPOXIDATION
  • STABLE CARBENES
  • IONIC LIQUIDS
  • UNFUNCTIONALIZED OLEFINS
  • ESTERIFICATION REACTION
  • NUCLEOPHILIC CARBENES
  • LIVING POLYMERIZATION

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