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Potassium 4‐Iodylbenzenesulfonate: Preparation, Structure, and Application as a Reagent for Oxidative Iodination of Arenes
Author(s) -
Yusubov Mekhman S.,
Yusubova Roza Y.,
Nemykin Victor N.,
Maskaev Andrey V.,
Geraskina Margarita R.,
Kirschning Andreas,
Zhdankin Viktor V.
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201064
Subject(s) - chemistry , hypervalent molecule , reagent , iodine , halogenation , potassium , salt (chemistry) , aqueous solution , organic chemistry , inorganic chemistry
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.