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Synthesis 2008(15): 2373-2380  
DOI: 10.1055/s-2008-1067169
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Lukasz Kraszkiewicz, Lech Skulski*
Chair and Laboratory of Organic Chemistry, Faculty of Pharmacy, Medical University, 1 Banacha Street, 02-097 Warsaw, Poland
Fax: +48(22)5720643.; e-Mail: lechskulski@yahoo.com.;
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Publikationsverlauf

Received 18 March 2008
Publikationsdatum:
08. Juli 2008 (online)

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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

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