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Related Concept Videos

Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

1.8K
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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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

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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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Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

1.5K
In a radical reaction, the concentration of starting materials governs the selectivity of a radical. For example, the reaction between an alkyl halide and an alkene, in the presence of tin hydride and AIBN, begins with the generation of a tin radical. The generated radical then abstracts halogen from the alkyl halide, producing an alkyl radical. This alkyl radical can either react with tin hydride, yielding an alkane, or add to an alkene, generating a nitrile-stabilized radical, eventually...
1.5K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.2K
Radicals adjacent to electron-donating groups are called nucleophilic radicals. These radicals readily react with electrophilic alkenes. The SOMO–LUMO interactions are the driving force for the reaction, where the high-energy SOMO of the electron-rich, nucleophilic radicals interacts with the low-energy LUMO of the electron-deficient, electrophilic alkenes. Such SOMO–LUMO interactions are the basis of reactive radical traps, affecting the selectivity in radical reactions. For...
2.2K
Radical Formation: Addition00:47

Radical Formation: Addition

1.8K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
1.8K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

1.9K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation...
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Updated: Sep 9, 2025

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

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Recent Advances in Iodine-Mediated Radical Reactions.

Wen Yang1, Jian Guo2, Samual Hee2,3

  • 1College of Chemistry and Chemical Engineering, Jiangxi Province Engineering Research Center of Ecological Chemical Industry, Jiujiang Key Laboratory of Organosilicon Chemistry and Application, Jiujiang University, Jiujiang, 332005, People's Republic of China.

Advanced Synthesis & Catalysis
|September 2, 2025
PubMed
Summary

This review updates recent advances in iodine-mediated radical reactions for organic synthesis. It categorizes mechanisms, focusing on covalent/noncovalent bond formation, radical generation, and peroxide decomposition pathways.

Keywords:
halogen bondinghomolysisiodine catalysisradical reactionsingle electron transfer

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Area of Science:

  • Organic Chemistry
  • Radical Chemistry
  • Synthetic Methodology

Background:

  • Iodine-mediated radical reactions offer alternatives to traditional ionic pathways in organic synthesis.
  • Significant progress has been made in this field over the last two decades.

Purpose of the Study:

  • To provide a comprehensive update on iodine-mediated radical reactions in organic synthesis from 2015 to mid-2024.
  • To organize these reactions based on their mechanistic pathways.

Main Methods:

  • Review of literature reporting iodine-mediated radical reactions.
  • Classification of reaction mechanisms into four categories based on radical initiation.

Main Results:

  • Detailed overview of four mechanistic pathways: covalent X-I bond formation, noncovalent N···I bond assisted homolysis, direct iodine radical generation (photochemical, thermal, electrochemical), and iodine-induced peroxide decomposition via SET.
  • Compilation of recent advancements in iodine-mediated radical reactions.

Conclusions:

  • Iodine-mediated radical reactions are a versatile tool in modern organic synthesis.
  • This review serves as a valuable resource and inspiration for future research in this rapidly developing field.