Diaryliodonium salts have been shown to react with fluoride ion at 80 °C in acetonitrile to generate aryl fluorides. The regioselectivity is controlled electronically and by the bulk of the ortho-substituents on the rings, with the latter the dominant factor such that electron-rich rings can be fluorinated. ortho-Substituted aryl fluorides can be selectively produced from unsymmetrical diaryliodonium salts. The process has been used to synthesise [18F] labelled aromatics by the use of cyclotron generated [18F]fluoride ion.
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Journal of the Chemical Society, Perkin Transactions 1
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