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 language | English (US) |
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Pages (from-to) | 2653-2675 |
Number of pages | 23 |
Journal | Advanced Synthesis and Catalysis |
Volume | 365 |
Issue number | 16 |
DOIs | |
State | Published - Aug 15 2023 |
Externally published | Yes |
Bibliographical note
Funding Information:This work was supported partly by JST CREST (No. JPMJCR19R2 for A.S.), and the JSPS Fund for the Promotion of Joint International Research (Grant No. 16KK0199 for A.S.). V.V.Z. and A.Y. are thankful to the National Science Foundation (CHE‐1759798) for support of their research program on hypervalent iodine chemistry at University of Minnesota Duluth.
Publisher Copyright:
© 2023 Wiley-VCH GmbH.
Keywords
- benziodoxole
- hypervalent iodine
- iodine
- iodine heterocycles
- ligand transfer