Suzuki-Miyaura cross-coupling reactions mediated by palladium/imidazolium salt systems

G A Grasa, M S Viciu, J K Huang, C M Zhang, M L Trudell, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

337 Citations (Scopus)

Abstract

Nucleophilic N-heterocyclic carbenes (NHC) have been used as ancillary ligands in palladium-mediated Suzuki-Miyaura cross-coupling reactions involving aryl chlorides or aryl triflates with arylboronic acids. The scope of the coupling process using Pd(0) or Pd(II) sources and an imidazolium salt in the presence of a base, Cs2CO3, was tested using various substrates. The Pd(OAc)(2) or Pd-2(dba)(3)/IMes.HCl (2, IMes = 1,3-bis(2,4,6-trimethylphenyl)-imidazol-2-ylidene) system presents very high activity with respect to electron-neutral and electron-rich aryl chlorides. The ligand IPr.HCl (3, IPr = 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene) is also effective for the Suzuki-Miyaura cross-coupling involving a wide spectrum of aryl chlorides and aryl triflates. The general protocol developed has been applied successfully to the synthesis of an antiinflammatory drug (Fenbufen) and to a key intermediate in the synthesis of sartans. Mechanistically, palladium-to-ligand ratio studies support an active palladium species bearing one nucleophilic carbene ligand.

Original languageEnglish
Pages (from-to)2866-2873
Number of pages8
JournalOrganometallics
Volume21
Issue number14
DOIs
Publication statusPublished - 8 Jul 2002

Keywords

  • N-HETEROCYCLIC CARBENES
  • PALLADIUM-CATALYZED AMINATION
  • ASTERISK = ETA(5)-C5ME5
  • ARYL CHLORIDES
  • NUCLEOPHILIC-CARBENE
  • OLEFIN METATHESIS
  • ROOM-TEMPERATURE
  • ORGANOBORON COMPOUNDS
  • GRIGNARD-REAGENTS
  • ARYLBORONIC ACIDS

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