(IPr)Pd(acac)Cl: An easily synthesized, efficient, and versatile precatalyst for C-N and C-C bond formation

N Marion, EC Ecarnot, O Navarro, D Amoroso, A Bell, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

163 Citations (Scopus)

Abstract

A very straightforward synthesis of (IPr) Pd(acac)Cl from two commercially available starting materials, Pd(acac)(2) and IPr center dot HCl [acac = acetylacetonate; IPr = N,N'-bis(2,6-diisopropylphenyl)imidazol-2-ylidene], has been developed. The resulting complex, ( IPr) Pd( acac) Cl ( 1), has proven to be a highly active Pd-II precatalyst in the Buchwald-Hartwig and the alpha-ketone arylation reactions. A wide range of substrates has been screened, including unactivated, sterically hindered, and heterocyclic aryl chlorides.

Original languageEnglish
Pages (from-to)3816-3821
Number of pages6
JournalThe Journal of Organic Chemistry
Volume71
Issue number10
DOIs
Publication statusPublished - 12 May 2006

Keywords

  • n
  • PALLADIUM-CATALYZED AMINATION
  • CROSS-COUPLING REACTIONS
  • ALPHA-ARYLATION
  • ARYL CHLORIDES
  • ELECTRON-TRANSFER
  • ENERGY-TRANSFER
  • BROMIDES
  • LIGAND
  • KETONES
  • ARYLAMINES

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