Potassium 4-iodylbenzenesulfonate: Preparation, structure, and application as a reagent for oxidative iodination of arenes

Mekhman S. Yusubov, Roza Y. Yusubova, Victor N. Nemykin, Andrey V. Maskaev, Margarita R. Geraskina, Andreas Kirschning, Viktor Vladimirovich Zhdankin

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18 Citations (Scopus)

Abstract

A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by the oxidation of 4-iodobenzensulfonic acid with Oxone in water. This potassium salt can be further converted into 4-iodylbenzenesulfonic acid by treatment with the acidic form of Amberlyst 15 in water. A single-crystal X-ray structure of potassium 4-iodylbenzenesulfonate revealed the presence of polymeric chains in the solid state due to a combination of numerous intra- and intermolecular interactions. Potassium 4-iodylbenzenesulfonate will likely find many practical applications as a thermally stable and water-soluble hypervalent iodine-based oxidant, particularly useful as a reagent for oxidative iodination of aromatic substrates. This reagent can be effectively recovered from the reaction mixture (92 % recovery) by treatment of the aqueous layer with Oxone at 60°C for 2 h, followed by filtration of the precipitate. A new hypervalent iodine(V) compound, potassium 4-iodylbenzenesulfonate, was prepared by oxidation of 4-iodobenzenesulfonic acid with Oxone in water. This new reagent promises many practical applications as a thermally stable, water-soluble and recyclable hypervalent iodine oxidant, particularly useful for oxidative iodination of aromatic substrates.

Original languageEnglish
Pages (from-to)5935-5942
Number of pages8
JournalEuropean Journal of Organic Chemistry
Issue number30
DOIs
Publication statusPublished - Oct 2012

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Keywords

  • Hypervalent compounds
  • Iodination
  • Iodine
  • Oxidation
  • X-ray diffraction

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

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