2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents

Mekhman S. Yusubov, Pavel S. Postnikov, Roza Ya Yusubova, Akira Yoshimura, Gerrit Jürjens, Andreas Kirschning, Viktor V. Zhdankin

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


Two powerful hypervalent iodine(V) oxidants, DMP-OTs (1-tosyloxy-1,1-diacetoxy-1H-1λ5-benzo[d][1,2]iodoxol-3-one) and IBX-OTs (1-tosyloxy-1-oxo-1H-1λ5-benzo[d][1,2]iodoxol-3-one) show high reactivity in the oxidation of structurally complex primary and secondary alcohols, which are highly functionalized polyketide or terpene fragments or steroids. The yields of the corresponding carbonyl compounds are even higher for the protocol that uses pyridine as additive. The oxidations proceed very rapidly at room temperature leaving the protective groups and π-systems intact and affording the corresponding carbonyl compounds in good to excellent yields. Moreover, IBX-OTs is an efficient reagent for the oxidative dehydrogenation of steroidal alcohols to the corresponding enones. (Figure presented.).

Original languageEnglish (US)
Pages (from-to)3207-3216
Number of pages10
JournalAdvanced Synthesis and Catalysis
Issue number18
StatePublished - Sep 18 2017

Bibliographical note

Funding Information:
This work was supported by research grants from the Russian Science Foundation (RSF-16-13-10081) and the National Science Foundation (CHE-1262479).

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


  • alcohols
  • iodine
  • oxidation
  • synthetic methods
  • terpenoids


Dive into the research topics of '2-Iodoxybenzoic Acid Tosylates: the Alternative to Dess–Martin Periodinane Oxidizing Reagents'. Together they form a unique fingerprint.

Cite this