Catalytic dehalogenation of aryl halides mediated by a palladium/imidazolium salt system

M S Viciu, G A Grasa, Steven Patrick Nolan

Research output: Contribution to journalArticlepeer-review

156 Citations (Scopus)

Abstract

A convenient and efficient catalytic aryl halide dehalogenation protocol has been developed using an imidazolium salt/palladium/base system. The use of the ligand precursor SIMes . HCl ((2,4,6-trimethylphenyl)dihydroimidazolium chloride) in conjunction with Pd(dba)2 was found to be most effective for the dehalogenation of aryl chlorides, bromides, and polyhalogenated aromatic hydrocarbons. Strong bases having beta -hydrogens both perform deprotonation of the imidazolium salt and are hydrogen sources for the dehalogenation process. The oxidative addition of the imidazolium salt to the palladium(0) precursor generating a carbene palladium hydride species may also be involved in the dehalogenation process. This oxidative-addition reaction may have fundamental implications in low-valent metal carbene mediated transformations.

Original languageEnglish
Pages (from-to)3607-3612
Number of pages6
JournalOrganometallics
Volume20
Issue number16
DOIs
Publication statusPublished - 6 Aug 2001

Keywords

  • OLEFIN METATHESIS CATALYSTS
  • N-HETEROCYCLIC CARBENES
  • CROSS-COUPLING REACTION
  • ORGANIC HALIDES
  • ARYLBORONIC ACIDS
  • AROMATIC HALIDES
  • REDUCTIVE DEHALOGENATION
  • TRANSFER HYDROGENOLYSIS
  • NICKEL-COMPLEXES
  • SODIUM HYDRIDE

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