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Radical reactions can occur either intermolecularly or intramolecularly. In an intermolecular radical reaction, a nucleophilic radical adds to an electrophilic alkene or vice versa. In such reactions, the radical and generally the alkene, which is also called the radical trap, are two different molecules. Additionally, for such intermolecular reactions to occur, the radical trap must be active, present in an excess concentration, and the radical starting material must have a weak...
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Radicals, the highly reactive species, gain stability by undergoing three different reactions. The first reaction involves a radical-radical coupling, in which a radical combines with another radical, forming a spin‐paired molecule. The second reaction is between a radical and a spin‐paired molecule, generating a new radical and a new spin‐paired molecule. The third reaction is radical decomposition in a unimolecular reaction, forming a new radical and a spin‐paired...
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Iodanyl Radical Catalysis.

Asim Maity1, Brandon L Frey1, David C Powers1

  • 1Texas A&M University, College Station, Texas 77843, United States.

Accounts of Chemical Research
|July 6, 2023
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Summary
This summary is machine-generated.

This study reveals that iodanyl radicals, previously overlooked, are key intermediates in sustainable hypervalent iodine chemistry and catalysis. Harnessing these open-shell species enables novel I(I)/I(II) catalytic cycles, advancing organoiodide applications.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Main-group Chemistry

Background:

  • Hypervalent iodine reagents are versatile oxidants, typically involving two-electron redox transformations (I(I)/I(III), I(III)/I(V)).
  • One-electron redox chemistry and iodine radical behavior are established in inorganic systems but less explored in organic hypervalent iodine chemistry.
  • Transient iodanyl radicals (formally I(II) species) are emerging as potential intermediates, though their role in substrate functionalization and catalysis remains largely unknown.

Purpose of the Study:

  • To advance the chemistry of iodanyl radicals as intermediates in sustainable synthesis of hypervalent iodine compounds.
  • To explore iodanyl radicals as platforms for substrate activation via open-shell main-group intermediates.
  • To investigate the catalytic potential of iodanyl radicals as an alternative to traditional two-electron redox cycles.

Main Methods:

  • Investigated aerobic hypervalent iodine catalysis in aldehyde autoxidation.
  • Conducted detailed mechanistic studies to elucidate the role of iodanyl radical intermediates.
  • Developed hypervalent iodine electrocatalysis, identifying new catalyst design principles.
  • Isolated and characterized anodically generated iodanyl radical intermediates.
  • Experimentally validated substrate activation via proton-coupled electron transfer (PCET) and disproportionation reactions of I(II) species.

Main Results:

  • Demonstrated the critical role of acetate-stabilized iodanyl radicals in aerobic aldehyde autoxidation.
  • Developed efficient organoiodide electrocatalysts operating at modest potentials, overcoming challenges of high potentials and catalyst loadings.
  • Successfully isolated iodanyl radical intermediates, enabling direct study of their reaction mechanisms.
  • Confirmed substrate activation through bidirectional PCET at I(II) intermediates.
  • Validated disproportionation of I(II) species to generate I(III) compounds.

Conclusions:

  • Emerging synthetic and catalytic chemistry of iodanyl radicals is highlighted.
  • Open-shell iodanyl radicals play a crucial role in sustainable synthesis and catalysis.
  • The development of I(I)/I(II) catalytic cycles offers a mechanistic alternative to conventional two-electron iodine redox chemistry.
  • This research opens new avenues for the application of organoiodides in catalysis.