First Kumada reaction of alkyl chlorides using N-heterocyclic carbene/palladium catalyst systems

Anja C. Frisch, Franck Rataboul, Alexander Zapf, Matthias Beller

Research output: Contribution to journalArticlepeer-review

98 Scopus citations

Abstract

For the first time it is shown that N-heterocyclic carbenes are suitable ligands for the palladium-catalyzed coupling of alkyl chlorides with aryl Grignard reagents. A variety of simple as well as functionalized primary alkyl chlorides provide the corresponding alkyl benzenes in general in good to very good yield. By comparing the 1,3-dimesitylimidazol-2-ylidene (IMes) palladium(0) naphthoquinone complex with the previously known palladium phosphine catalyst for the model coupling reaction of 1-chlorohexane with phenylmagnesium bromide it is demonstrated that the new catalyst system is superior.

Original languageEnglish
Pages (from-to)403-409
Number of pages7
JournalJournal of Organometallic Chemistry
Volume687
Issue number2
DOIs
StatePublished - 7 Dec 2003
Externally publishedYes

Keywords

  • Alkyl chlorides
  • N-heterocyclic carbenes
  • Palladium-catalyzed coupling

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