Recent Progress in Synthetic Applications of Cyclic Hypervalent Iodine(III) Reagents

Akira Yoshimura, Akio Saito, Viktor V. Zhdankin

Research output: Contribution to journalReview articlepeer-review

10 Scopus citations

Abstract

Hypervalent iodine compounds have found broad application in modern organic chemistry as reagents and catalysts. Cyclic hypervalent iodine reagents based on the benziodoxole heterocyclic system have higher stability compared to their acyclic analogues, which makes possible the preparation and safe handling of the reagents with special ligands such as azido, cyano, and trifluoromethyl groups. Numerous iodine-substituted benziodoxole derivatives have been prepared and utilized as reagents for transfer of the substituent on hypervalent iodine to organic substrate. Reactions of these reagents with organic substrates can be performed under metal-free conditions, in the presence of transition metal catalysts, or using photocatalysts under photoirradiation conditions. In this review, we focus on the most recent synthetic applications of cyclic hypervalent iodine(III) reagents with the following ligands: N3, NHR, CN, CF3, SCF3, OR, OAc, ONO2, and C(=N2)CO2R. The review covers literature published mainly in the last 5 years.

Original languageEnglish (US)
Pages (from-to)2653-2675
Number of pages23
JournalAdvanced Synthesis and Catalysis
Volume365
Issue number16
DOIs
StatePublished - Aug 15 2023
Externally publishedYes

Bibliographical note

Publisher Copyright:
© 2023 Wiley-VCH GmbH.

Keywords

  • benziodoxole
  • hypervalent iodine
  • iodine
  • iodine heterocycles
  • ligand transfer

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