Facile Syntheses of Symmetrical Diaryliodonium Salts from Various Arenes, with Sodium Metaperiodate as the Coupling Reagent in Acidic Media [¹]

Abstract

An easy, inexpensive, safe, and effective preparative procedure to obtain symmetrical diaryliodonium bromides (in 17-88% crude yields) from various arenes is presented in this paper. A novel method for the in situ preparation of iodosyl sulfate (Chrétien’s reagent) is given. Eleven exemplary crude diaryliodonium bromides were readily oxidatively metathesized with 40% aqueous tetrafluoroboric acid and 30% aqueous hydrogen peroxide (in boiling acetone, used both as a solvent and ‘halogen scavenger’) to give pure diaryliodonium tetrafluoroborates in 15-85% yields.

Key words

symmetrical diaryliodonium salts - arenes - sodium metaperiodate - iodosyl sulfate - oxidative anion metatheses

References

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10

Frohn, H. J. unpublished results related in ref 2c, pp 215-217.