Improving palladium-catalyzed cyanation of aryl halides: Development of a state-of-the-art methodology using potassium hexacyanoferrate(II) as cyanating agent

Thomas Schareina, Alexander Zapf, Matthias Beller

Research output: Contribution to journalArticlepeer-review

191 Scopus citations

Abstract

Benzonitriles are easily accessible via palladium-catalyzed cyanation of aryl halides using potassium hexacyanoferrate(II) as cyanide source. This method is applicable on both activated and deactivated aryl and heteroaryl bromides and activated chlorides giving the corresponding benzonitriles in good to excellent yield. Advantageously, the used cyanating agent is non-toxic and cheap. The presented catalyst system is rather simple and it is not necessary to add expensive phosphines, making the novel method also attractive for industrial applications. Benzonitriles are easily accessible via palladium-catalyzed cyanation of aryl halides using potassium hexacyanoferrate(II) as cyanide source. This method is applicable on both activated and deactivated aryl and heteroaryl bromides and activated chlorides giving the corresponding benzonitriles in good to excellent yield. Advantageously, the used cyanating agent is non-toxic and cheap. The presented catalyst system is rather simple and it is not necessary to add expensive phosphines, making the novel method also attractive for industrial applications.

Original languageEnglish
Pages (from-to)4576-4583
Number of pages8
JournalJournal of Organometallic Chemistry
Volume689
Issue number24 SPEC. ISS.
DOIs
StatePublished - 29 Nov 2004
Externally publishedYes

Keywords

  • Aryl halides
  • Benzonitriles
  • Cyanation
  • Homogeneous catalysis
  • Palladium
  • Potassium hexacyanoferrate(II)

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