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Synthesis 1995; 1995(8): 1027-1032
DOI: 10.1055/s-1995-4045
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A Short-Cut Synthesis of Diaryliodonium Bromides Followed by Oxidative Anion Metatheses

Paweł Kaźmierczak, Lech Skulski*
  • *Chair and Laboratory of Organic Chemistry, Medical Academy, Banach 1, PL 02-097 Warsaw, Poland, Fax +48(22)231487
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Publication Date:
31 December 2000 (online)

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This paper reports a one-pot synthesis of the title bromides (in 20-88% crude yields) from iodoarenes oxidized with the CrO3/AcOH/Ac2O/H2SO4 liquid mixture, then coupled in situ with arenes and, finally, precipitated out with a KBr solution. Similarly, diaryliodonium perchlorates and iodides are obtained in 40-89% crude yields. Oxidative anion metatheses in the crude title bromides produce the respective pure diaryliodonium tetrafluoroborates, tosylates, trifluoroacetates, hydrosulfates, nitrates, and chlorides in 57-80% yields. These new preparative procedures are easier and shorter than many earlier methods.

One-pot synthesis of diaryliodonium bromides from iodoarenes and arenes followed by oxidative anion metatheses.