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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: Intramolecular vs Intermolecular01:33

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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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Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

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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...
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Radical Reactivity: Concentration Effects01:20

Radical Reactivity: Concentration Effects

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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...
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Radical Reactivity: Steric Effects01:10

Radical Reactivity: Steric Effects

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The presence of electron-donating, electron-withdrawing, or conjugating groups adjacent to a radical center, imparts electronic stabilization to the radicals. Examples of such electronically-stabilized radicals are triphenylmethyl, tetramethylpiperidine‐N‐oxide, and 2,2‐diphenyl‐1‐picrylhydrazyl. These radicals are remarkably stable and are known as persistent radicals. Some of the persistent radicals can even be isolated and purified.
Along with electronic...
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Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.4K
Radicals adjacent to electron‐withdrawing groups are called electrophilic radicals. These radicals readily react with nucleophilic alkenes. For example, the malonate radical, in which the radical center is flanked by two electron‐withdrawing groups, reacts readily with butyl vinyl ether, which consists of an electron‐donating oxygen substituent. The reaction between electrophilic malonate radical and nucleophilic vinyl ether is favored because the radical has a...
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Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Reacciones de acoplamiento cruzado intermolecular altamente selectivas a través de un efecto radical persistente

Huaming Zhu1, Junbo Wang1,2, Yong Zhang3

  • 1School of Physics and Information Technology, Shaanxi Normal University, Xi'an 710119, China.

Journal of the American Chemical Society
|October 25, 2025
PubMed
Resumen
Este resumen es generado por máquina.

Desarrollamos una nueva reacción de acoplamiento radical en superficies de plata, logrando más del 99% de selectividad empleando el efecto radical persistente. Este avance supera un gran desafío en la química radical.

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Área de la Ciencia:

  • Ciencias de la superficie
  • Química radical
  • Microscopía con sonda de exploración

Sus antecedentes:

  • El acoplamiento radical es un desafío debido al homoacoplamiento.
  • El acoplamiento selectivo de radicales es crucial para la síntesis química.

Objetivo del estudio:

  • Para lograr una alta selectividad en las reacciones de acoplamiento cruzado radical.
  • Para aclarar el mecanismo de acoplamiento radical en las superficies.

Principales métodos:

  • Se utiliza el efecto de los radicales persistentes en la superficie de Ag{111).
  • Se utiliza el microscopio de túnel de barrido de resolución de enlaces (BR-STM) para la visualización.
  • Datos experimentales combinados con cálculos de la teoría funcional de la densidad (DFT) y modelado numérico.

Principales resultados:

  • Se ha logrado una selectividad >99% en el acoplamiento radical.
  • Intermedios y productos de reacción directamente visualizados a nivel de enlace único.
  • Se aclaró el mecanismo de reacción y la cinética del efecto radical persistente.

Conclusiones:

  • El efecto radical persistente permite el acoplamiento radical altamente selectivo en las superficies.
  • BR-STM es una herramienta poderosa para estudiar las reacciones superficiales a nivel molecular.
  • Comprender la cinética radical es clave para controlar las reacciones superficiales.