A general and versatile approach to thermally generated N-heterocyclic carbenes

Gregory W. Nyce, Szilard Csihony, Robert M. Waymouth, James L. Hedrick

Research output: Contribution to journalArticle

168 Citations (Scopus)


The synthesis of N-heterocyclic carbene (NHC) adducts by condensation of diamines with appropriately substituted benzaldehydes is described. This simplified approach provides the NHC adduct without first having to generate the carbene followed by its protection. These adducts undergo thermal deprotection to generate N-heterocyclic carbene in situ. Adduct decomposition temperatures were investigated as a function of catalyst structure by using thermal analysis and spectroscopic techniques. Importantly, unlike adducts derived from chloroform, the new pentafluorobenzene-based adducts are more readily prepared and are stable at room temperature. The utility of these adducts as organic catalyst precursors for living ring-opening polymerization (ROP) of lactide, transesterification reactions, and the synthesis of N-heterocyclic carbene ligated organometallic complexes is also described.

Original languageEnglish
Pages (from-to)4073-4079
Number of pages7
JournalChemistry - A European Journal
Issue number16
Publication statusPublished - Aug 20 2004


  • Carbenes
  • Nitrogen heterocycles
  • Organic catalysis
  • Organometallic complexes

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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