Copper-carbene complexes as catalysts in the synthesis of functionalized styrenes and aliphatic alkenes

Helene Lebel, Michael Davi, Silvia Diez-Gonzalez, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

83 Citations (Scopus)

Abstract

[GRAPHICS]

(NHC) -Cu (NHC= N-heterocyclic carbene) complexes efficiently catalyzed the methylenation of a variety of aliphatic and aromatic aldehydes and ketones in the presence of trimethylsilyldiazomethane, triphenylphosphine, and 2-propanol. The copper catalysts are not only inexpensive compared to rhodium complexes, but they also exhibit better functional group compatibility with aromatic aldehydes and ketones. Indeed very high yields were obtained for the formation of styrenes containing nitro, trifluoromethyl, amino, and ester groups, as well as for pyridine-, pyrrole-, and indole-substituted alkenes.

Original languageEnglish
Pages (from-to)144-149
Number of pages6
JournalThe Journal of Organic Chemistry
Volume72
Issue number1
DOIs
Publication statusPublished - 5 Jan 2007

Keywords

  • N-HETEROCYCLIC CARBENE
  • ALDEHYDE-OLEFINATION CATALYSTS
  • MAIN-GROUP ELEMENTS
  • ALKOXY-NHC LIGANDS
  • ETHYL DIAZOACETATE
  • CARBONYL-COMPOUNDS
  • CONJUGATE ADDITION
  • PORPHYRIN COMPLEX
  • SELECTIVE OLEFINATION
  • TRANSITION-METALS

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