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Facile Syntheses of Symmetrical Diaryliodonium Salts from Various Arenes, with Sodium Metaperiodate as the Coupling Reagent in Acidic Media
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1  Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical Univesity, 1 Banacha Street, 02-097 Warsaw, Poland

Abstract: Easy, cheap, safe and effective preparative procedures to obtain symmetrical diaryliodonium bromides (in 15-88% crude yields) from various arenes are presented in this paper. A novel method for preparing iodosyl sulfate (Chrétien’s reagent) is given. Several crude diaryliodonium bromides were readily oxidatively metathesized with 30% aq. H2O2 and 40% aq. HBF4 (in acetone, used both as a solvent and “halogen scavenger”) to give pure diaryliodonium tetrafluoroborates in 64-85% yields.
Keywords: symmetrical diaryliodonium salts; arenes; sodium metaperiodate; iodosyl sulfate; oxidative anion metatheses