Suzuki-Miyaura, alpha-ketone arylation and dehalogenation reactions catalyzed by a versatile N-heterocyclic carbene-palladacycle complex

O Navarro, N Marion, Y Oonishi, RA Kelly, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

232 Citations (Scopus)

Abstract

[GRAPHICS]

The activity of the complex (IPr)PdCl(eta(2)-N,C-C12H7NMe2), 1 [IPr = (N,N'-bis(2,6-diisopropylphenyl)-imidazol)-2-ylidene], in the Suzuki-Miyaura cross-coupling reaction involving unactivated aryl chlorides and triflates with arylboronic acids at room temperature in technical, grade 2-propanol is described. These conditions allow for the synthesis of di- and tri-ortho-substituted biaryls in very short reaction times. This complex also displays very high activity for (x-ketone arylation and dehalogenation reactions of activated and unactivated aryl chlorides.

Original languageEnglish
Pages (from-to)685-692
Number of pages8
JournalThe Journal of Organic Chemistry
Volume71
Issue number2
DOIs
Publication statusPublished - 20 Jan 2006

Keywords

  • CROSS-COUPLING REACTION
  • HIGHLY EFFICIENT CATALYSTS
  • BOND-FORMING REACTIONS
  • ARYL CHLORIDES
  • C-C
  • TRIARYLPHOSPHITE COMPLEXES
  • ROOM-TEMPERATURE
  • NUCLEOPHILIC CARBENES
  • PHOSPHINITE COMPLEXES
  • PALLADIUM CATALYSTS

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