N-heterocyclic carbene-palladium complexes [(NHC)Pd(acac)Cl]: Improved synthesis and catalytic activity in large-scale cross-coupling reactions

Nicolas Marion, Pierre De Fremont, Iris M. Puijk, Elise C. Ecarnot, Dino Amoroso, Andrew Bell, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

68 Citations (Scopus)

Abstract

From two commercially available starting materials, improved one-step, multigram-scale syntheses of [(IPr)Pd(acac)Cl] [IPr=N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; acac=acetylacetonate] and [(IMes)Pd(acac)Cl] [IMes = N,]Vbis(2,4,6-trimethylphenyl)imidazol-2-ylidene] are described. The catalytic activity of both complexes in cross-coupling reactions has been examined. The most active pre-catalyst, [(IPr)Pd(acac)Cl], has allowed for efficient large-scale (10 mmol) Buch-wald-Hartwig and a-ketone arylation reactions to be carried out.

Original languageEnglish
Pages (from-to)2380-2384
Number of pages5
JournalAdvanced Synthesis & Catalysis
Volume349
Issue number14-15
DOIs
Publication statusPublished - Oct 2007

Keywords

  • n-aryl amination
  • cross-coupling
  • N-heterocyclic
  • carbene
  • a-ketone arylation
  • large-scale
  • palladium
  • SUZUKI-MIYAURA
  • (NHC)PD(ALLYL)CL NHC
  • ROOM-TEMPERATURE
  • ALPHA-ARYLATION
  • BUCHWALD-HARTWIG
  • BOND FORMATION
  • C-N
  • KETONE
  • TRANSFORMATIONS
  • CHEMISTRY

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