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Related Concept Videos

Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.5K
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 Formation: Homolysis00:54

Radical Formation: Homolysis

4.1K
A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
4.1K
Mass Spectrometry: Molecular Fragmentation Overview01:20

Mass Spectrometry: Molecular Fragmentation Overview

5.1K
The ionization of a molecule into a molecular ion inside the mass spectrometer causes instability in the molecule's structure due to the loss of an electron. This eventually leads to the fragmentation or breaking of some bonds in the molecule. The fragmentation occurs predominantly at specific bonds to yield relatively stable fragments.
One type of fragmentation pattern is the cleavage of a single bond in the molecular ion. The cleavage leads to a radical and a cation. The cleavage can occur at...
5.1K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.5K
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...
2.5K
Radical Formation: Overview01:03

Radical Formation: Overview

2.5K
A bond can be broken either by heterolytic bond cleavage to form ions or homolytic bond cleavage to yield radicals. A fishhook arrow is used to represent the motion of a single electron in homolytic bond cleavage. There are two main sources from which radicals can be formed:
Radicals from spin-paired molecules:
Radicals can be obtained from spin-paired molecules either by homolysis or electron transfer. While two radicals are formed in the former, an electron is added in the...
2.5K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.3K
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...
2.3K

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Phosphoranyl Radical Fragmentation Reactions Driven by Photoredox Catalysis.

James A Rossi-Ashton1, Aimee K Clarke1, William P Unsworth1

  • 1Department of Chemistry, University of York, Heslington, York YO10 5DD, U.K.

ACS Catalysis
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Phosphoranyl radicals are a key tool in photoredox catalysis for generating valuable radicals. This perspective reviews methods for their formation and diverse applications in chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Radical Chemistry

Background:

  • Phosphoranyl radicals are increasingly important in synthetic chemistry.
  • They enable the generation of diverse radical intermediates.
  • Applications include deoxygenation and desulfurization reactions.

Purpose of the Study:

  • To provide a comprehensive evaluation of phosphoranyl radicals in photoredox catalysis.
  • To highlight distinct methods for phosphoranyl radical formation.
  • To showcase the versatility of radical intermediates generated.

Main Methods:

  • Review of existing literature on phosphoranyl radicals in photoredox catalysis.
  • Analysis of radical addition and nucleophilic addition pathways for radical formation.
  • Evaluation of the reactivity profiles of generated radical intermediates.

Main Results:

  • Photocatalytic generation of phosphoranyl radicals is a rapidly developing field.
  • Two primary methods, radical and nucleophilic addition, yield phosphoranyl radicals.
  • These methods generate versatile radical intermediates with tunable reactivity.

Conclusions:

  • Phosphoranyl radicals serve as tunable mediators in photoredox catalysis.
  • Diverse radical intermediates can be accessed through controlled formation pathways.
  • This approach offers significant potential for synthetic organic chemistry.