Nuclear fluorination of 3,5-diarylisoxazoles with Selectfluor®

Chad E. Stephens, Jacqueline A. Blake

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17 Scopus citations

Abstract

C-4 Fluorination of a series of 3,5-diarylisoxazoles has been accomplished using the N-F reagent Selectfluor ®. With substrates containing neutral or activating substituents on the 5-phenyl ring, acetonitrile at room temperature or at reflux could be used as solvent. However, when deactivating substituents were present, a higher reaction temperature was required for which sulfolane was found to be a good solvent. At this higher temperature, a unique trifluorination of the isoxazole nucleus by an addition mechanism occurred as a side reaction.

Original languageEnglish (US)
Pages (from-to)1939-1945
Number of pages7
JournalJournal of Fluorine Chemistry
Volume125
Issue number12
DOIs
Publication statusPublished - Dec 1 2004
Externally publishedYes

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Keywords

  • Fluorination
  • Heterocycle
  • Isoxazole
  • Selectfluor
  • Substituent effects
  • Sulfolane

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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