2-(Fluorophenyl)pyridines by the Suzuki-Miyaura method: Ag2O accelerates coupling over undesired ipso substitution (SNAr) of fluorine

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Abstract

Problematic ipso substitution was observed in the Suzuki-Miyaura coupling of pentafluorophenylboronic acid to make 2-pentafluorophenylpyridine. Strong bases favored coupling, but under these conditions fluorine in the product tended to undergo nucleophilic substitution. Inclusion of Ag2O accelerated coupling over ipso substitution.

Original languageEnglish
Pages (from-to)1503-1506
Number of pages4
JournalTetrahedron Letters
Volume44
Issue number7
DOIs
StatePublished - Feb 10 2003

Bibliographical note

Funding Information:
The authors thank the NSF (0111578) for financial support.

Keywords

  • Aryl cross coupling
  • Pd catalyst
  • Suzuki coupling
  • Transmetallation

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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