Fluoride-promoted ligand exchange in diaryliodonium salts

B Wang, RL Cerny, SH Uppaluri, JJ Kempinger…

Index: Wang, Bijia; Cerny, Ronald L.; Uppaluri, Shriharsha; Kempinger, Jayson J.; Dimagno, Stephen G. Journal of Fluorine Chemistry, 2010 , vol. 131, # 11 p. 1113 - 1121

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Citation Number: 30

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 50mM substrate concentration. The reaction is slowed, but not halted if benzene is the solvent, indicating that free fluoride ion ...