Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications

Irina A. Mironova, Dmitrii M. Noskov, Akira Yoshimura, Mekhman S. Yusubov, Viktor V. Zhdankin

Research output: Contribution to journalReview articlepeer-review

10 Scopus citations

Abstract

Hypervalent iodine reagents are in high current demand due to their exceptional reactivity in oxidative transformations, as well as in diverse umpolung functionalization reactions. Cyclic hypervalent iodine compounds, known under the general name of benziodoxoles, possess improved thermal stability and synthetic versatility in comparison with their acyclic analogs. Aryl-, alkenyl-, and alkynylbenziodoxoles have recently received wide synthetic applications as efficient reagents for direct arylation, alkenylation, and alkynylation under mild reaction conditions, including transition metal-free conditions as well as photoredox and transition metal catalysis. Using these reagents, a plethora of valuable, hard-to-reach, and structurally diverse complex products can be synthesized by convenient procedures. The review covers the main aspects of the chemistry of benziodoxole-based aryl-, alkynyl-, and alkenyl- transfer reagents, including preparation and synthetic applications.

Original languageEnglish (US)
Article number2136
JournalMolecules
Volume28
Issue number5
DOIs
StatePublished - Mar 2023
Externally publishedYes

Bibliographical note

Funding Information:
This work was supported by the Russian Science Foundation (project No. 21-73-20031). V.V.Z. is thankful to the National Science Foundation (CHE-1759798) for support of his research program on hypervalent iodine chemistry at the University of Minnesota, Duluth.

Publisher Copyright:
© 2023 by the authors.

Keywords

  • alkynylation
  • arylation
  • benziodoxoles
  • benzyne
  • EBX
  • functionalization
  • hypervalent iodine
  • VBX
  • vinylation

PubMed: MeSH publication types

  • Journal Article
  • Review

Fingerprint

Dive into the research topics of 'Aryl-, Akynyl-, and Alkenylbenziodoxoles: Synthesis and Synthetic Applications'. Together they form a unique fingerprint.

Cite this