Fluoride-promoted ligand exchange in diaryliodonium salts

Bijia Wang, Ronald Cerny, Shriharsha Uppaluri, Jayson J. Kempinger, Stephen G. Dimagno

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Abstract

Diaryliodonium salts are shown to undergo rapid, fluoride-promoted aryl exchange reactions at room temperature in acetonitrile. Aryl exchange is shown to be exquisitely sensitive to the concentration of fluoride ion in solution; fast exchange is observed as the fluoride concentration approaches a stoichiometric amount at 50 mM substrate concentration. The reaction is slowed, but not halted if benzene is the solvent, indicating that free fluoride ion or a four-coordinate anionic I(III) species may be responsible for the exchange. The fluoride-promoted aryl exchange reaction is general and allows direct measurement of the relative stabilities of diaryliodonium salts featuring different aryl substituents. The aryl exchange reaction may be of practical use for the preparation of hitherto inaccessible diaryliodonium salts, thus it also has implications for labeling radiotracers for molecular imaging with 18F-fluoride (t1/2 = 109.7 min).

Original languageEnglish (US)
Pages (from-to)1113-1121
Number of pages9
JournalJournal of Fluorine Chemistry
Volume131
Issue number11
DOIs
Publication statusPublished - Nov 1 2010

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Keywords

  • Aryl fluorides
  • Diaryliodonium salts
  • F
  • Fluorination
  • Ligand exchange
  • PET
  • Reductive elimination

ASJC Scopus subject areas

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

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