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 language | English |
|---|---|
| Pages (from-to) | 5935-5942 |
| Number of pages | 8 |
| Journal | European Journal of Organic Chemistry |
| Issue number | 30 |
| DOIs | |
| Publication status | Published - 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
Cite this
Potassium 4-iodylbenzenesulfonate : Preparation, structure, and application as a reagent for oxidative iodination of arenes. / Yusubov, Mekhman S.; Yusubova, Roza Y.; Nemykin, Victor N.; Maskaev, Andrey V.; Geraskina, Margarita R.; Kirschning, Andreas; Zhdankin, Viktor Vladimirovich.
In: European Journal of Organic Chemistry, No. 30, 10.2012, p. 5935-5942.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Potassium 4-iodylbenzenesulfonate
T2 - Preparation, structure, and application as a reagent for oxidative iodination of arenes
AU - Yusubov, Mekhman S.
AU - Yusubova, Roza Y.
AU - Nemykin, Victor N.
AU - Maskaev, Andrey V.
AU - Geraskina, Margarita R.
AU - Kirschning, Andreas
AU - Zhdankin, Viktor Vladimirovich
PY - 2012/10
Y1 - 2012/10
N2 - 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.
AB - 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.
KW - Hypervalent compounds
KW - Iodination
KW - Iodine
KW - Oxidation
KW - X-ray diffraction
UR - http://www.scopus.com/inward/record.url?scp=84867598061&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84867598061&partnerID=8YFLogxK
U2 - 10.1002/ejoc.201201064
DO - 10.1002/ejoc.201201064
M3 - Article
SP - 5935
EP - 5942
JO - Annalen der Pharmacie
JF - Annalen der Pharmacie
SN - 0075-4617
IS - 30
ER -