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Related Concept Videos

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 Reactivity: Overview01:11

Radical Reactivity: Overview

2.2K
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...
2.2K
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...
1.8K
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 Substitution: Allylic Chlorination01:31

Radical Substitution: Allylic Chlorination

2.6K
Typically, when alkenes react with halogens at low temperatures, an addition reaction occurs. However, upon increasing the temperature or under reaction conditions that form radicals, providing a low but steady concentration of halogen radicals, allylic substitution reaction is favored. This is because allylic hydrogens are very reactive as the formed intermediate is resonance stabilized. For example, when propene is treated with chlorine in the gas phase at 400 °C, it undergoes allylic...
2.6K
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

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst
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Copper-catalyzed radical relay in C(sp3)-H functionalization.

Zuxiao Zhang1, Pinhong Chen2, Guosheng Liu2

  • 1Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Department of Chemistry, Zhejiang Normal University, 688 Yingbin Road, Jinhua 321004, China.

Chemical Society Reviews
|February 10, 2022
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Summary

Copper-catalyzed radical relay enables selective C(sp³)-H functionalization by combining hydrogen atom transfer and cross-coupling. Advances in ligand design are driving progress in asymmetric C-H functionalization strategies.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Radical-involved transition metal (TM) catalysis has revolutionized synthetic chemistry.
  • Copper catalysis offers unique advantages in C(sp³)-H functionalization.
  • Hydrogen atom transfer (HAT) provides regioselectivity, while copper cross-coupling offers versatility.

Purpose of the Study:

  • To review recent advances in copper-catalyzed radical relay for C(sp³)-H functionalization.
  • To highlight the role of ligand design in achieving asymmetric C-H functionalization.
  • To inspire future research in selective C(sp³)-H functionalization.

Main Methods:

  • Exploration of radical-involved transition metal catalysis.
  • Application of copper-catalyzed radical relay mechanisms.
  • Development and analysis of ligand design for asymmetric catalysis.

Main Results:

  • Demonstration of copper-catalyzed radical relay's potential in C(sp³)-H functionalization.
  • Significant progress in asymmetric C-H functionalization via tailored ligand design.
  • Integration of hydrogen atom transfer (HAT) regioselectivity with copper cross-coupling versatility.

Conclusions:

  • Copper-catalyzed radical relay is a powerful strategy for C(sp³)-H functionalization.
  • Ligand design is crucial for achieving high selectivity and enantioselectivity.
  • This field holds significant promise for developing novel synthetic methodologies.