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Potassium 4-Iodylbenzenesulfonate: Preparation, Structure, and Application as a Reagent for Oxidative Iodination of Arenes

  作者 YUSUBOV MEKHMAN S; YUSUBOVA ROZA Y; NEMYKIN VICTOR N; MASKAEV ANDREY V; GERASKINA MARGARITA R; KIRSCHNING ANDREAS; ZHDANKIN VIKTOR V  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-30;  页码  5935-5942  
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[摘要]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 degrees C for 2 h, followed by filtration of the precipitate.

 
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