Synthetic applications of pseudocyclic hypervalent iodine compounds

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37 Citations (Scopus)

Abstract

Hypervalent iodine compounds have found wide practical application as versatile, efficient, and sustainable reagents for organic synthesis. Pseudocyclic hypervalent iodine derivatives are characterized by the presence of additional intramolecular non-covalent coordination at the iodine center, which leads to significant alteration of their physical and chemical properties. In comparison with common hypervalent iodine reagents, these pseudocyclic compounds have higher thermal stability, better solubility, and improved reactivity. In recent years, pseudocyclic hypervalent iodine reagents are increasingly used in organic synthesis as environmentally friendly selective oxidants and electrophiles. Furthermore, numerous enantioselective reactions mediated by chiral pseudocyclic hypervalent iodine species have been recently developed. In the present review, the preparation and structural features of pseudocyclic iodine(iii) and iodine(v) derivatives are discussed, and recent developments in their synthetic applications are summarized.

Original languageEnglish
Pages (from-to)4771-4781
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number21
DOIs
Publication statusPublished - 2016

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Iodine Compounds
iodine compounds
Iodine
iodine
reagents
Synthetic Chemistry Techniques
Derivatives
synthesis
Oxidants
chemical properties
Solubility
Chemical properties
Thermodynamic stability
thermal stability
solubility
reactivity
Physical properties
Hot Temperature
physical properties
preparation

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Biochemistry

Cite this

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abstract = "Hypervalent iodine compounds have found wide practical application as versatile, efficient, and sustainable reagents for organic synthesis. Pseudocyclic hypervalent iodine derivatives are characterized by the presence of additional intramolecular non-covalent coordination at the iodine center, which leads to significant alteration of their physical and chemical properties. In comparison with common hypervalent iodine reagents, these pseudocyclic compounds have higher thermal stability, better solubility, and improved reactivity. In recent years, pseudocyclic hypervalent iodine reagents are increasingly used in organic synthesis as environmentally friendly selective oxidants and electrophiles. Furthermore, numerous enantioselective reactions mediated by chiral pseudocyclic hypervalent iodine species have been recently developed. In the present review, the preparation and structural features of pseudocyclic iodine(iii) and iodine(v) derivatives are discussed, and recent developments in their synthetic applications are summarized.",
author = "Akira Yoshimura and Yusubov, {Mekhman Suleyman ogly} and Zhdankin, {Viktor Vladimirovich}",
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AU - Yusubov, Mekhman Suleyman ogly

AU - Zhdankin, Viktor Vladimirovich

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N2 - Hypervalent iodine compounds have found wide practical application as versatile, efficient, and sustainable reagents for organic synthesis. Pseudocyclic hypervalent iodine derivatives are characterized by the presence of additional intramolecular non-covalent coordination at the iodine center, which leads to significant alteration of their physical and chemical properties. In comparison with common hypervalent iodine reagents, these pseudocyclic compounds have higher thermal stability, better solubility, and improved reactivity. In recent years, pseudocyclic hypervalent iodine reagents are increasingly used in organic synthesis as environmentally friendly selective oxidants and electrophiles. Furthermore, numerous enantioselective reactions mediated by chiral pseudocyclic hypervalent iodine species have been recently developed. In the present review, the preparation and structural features of pseudocyclic iodine(iii) and iodine(v) derivatives are discussed, and recent developments in their synthetic applications are summarized.

AB - Hypervalent iodine compounds have found wide practical application as versatile, efficient, and sustainable reagents for organic synthesis. Pseudocyclic hypervalent iodine derivatives are characterized by the presence of additional intramolecular non-covalent coordination at the iodine center, which leads to significant alteration of their physical and chemical properties. In comparison with common hypervalent iodine reagents, these pseudocyclic compounds have higher thermal stability, better solubility, and improved reactivity. In recent years, pseudocyclic hypervalent iodine reagents are increasingly used in organic synthesis as environmentally friendly selective oxidants and electrophiles. Furthermore, numerous enantioselective reactions mediated by chiral pseudocyclic hypervalent iodine species have been recently developed. In the present review, the preparation and structural features of pseudocyclic iodine(iii) and iodine(v) derivatives are discussed, and recent developments in their synthetic applications are summarized.

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