Preparation, Structure, and Reactivity of Pseudocyclic Benziodoxole Tosylates: New Hypervalent Iodine Oxidants and Electrophiles

Akira Yoshimura, Scott C. Klasen, Michael T. Shea, Khiem C. Nguyen, Gregory T. Rohde, Akio Saito, Pavel S. Postnikov, Mekhman S. Yusubov, Victor N. Nemykin, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

New pseudocyclic benziodoxole tosylates were prepared by the treatment of 1-hydroxybenziodoxolones with p-toluenesulfonic acid or via ligand transfer reaction between PhI(OH)OTs (Koser's reagent) and substituted 2-iodobenzoic acids under mild condition. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.362 Å between oxygen and iodine in the iodoxole ring. Pseudocyclic benziodoxole tosylates readily react with various organic substrates as electrophiles or oxidants to afford the corresponding iodonium salts or the products of oxidation. Furthermore, these compounds can be used as efficient recyclable hypervalent iodine reagents. The reduced form of a pseudocyclic benziodoxole tosylate, 2-iodobenzoic acid, can be efficiently recovered from the reaction mixture by a simple acid–base liquid–liquid biphasic procedure.

Original languageEnglish (US)
Pages (from-to)691-695
Number of pages5
JournalChemistry - A European Journal
Volume23
Issue number3
DOIs
StatePublished - Jan 12 2017

Bibliographical note

Funding Information:
This work was supported by research grants from the National Science Foundation (CHE-1262479 and MRI-1420373), Russian Science Foundation (RSF-16-13-10081). A.S. is also thankful to JSPS Grants-in-Aid for Scientific Research (C) (Grant No 15K07852).

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

  • hypervalent iodine
  • iodine
  • iodonium salts
  • oxidation
  • recyclable reagents

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