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Related Concept Videos

Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.1K
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...
2.1K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

1.9K
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...
1.9K
Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

3.3K
The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
3.3K
Radicals: Electronic Structure and Geometry01:07

Radicals: Electronic Structure and Geometry

4.0K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
4.0K
Radical Reactivity: Overview01:11

Radical Reactivity: Overview

2.1K
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...
2.1K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

14.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Related Experiment Video

Updated: Jun 16, 2025

Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
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Metal-Bound Heteroatom Radicals: Advancing Site-Selective C-H Functionalization.

Jiayuan Li1, Tobias Blockhaus1, Guosheng Liu1

  • 1New Cornerstone Science Laboratory, State Key Laboratory of Organometallic Chemistry, and Shanghai Hongkong Joint Laboratory in Chemical Synthesis, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, University of Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

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Controlling radical selectivity in C-H functionalization is challenging. This review highlights how metal-bound radicals enable precise hydrogen atom abstraction for targeted transformations, advancing synthetic chemistry.

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Area of Science:

  • Synthetic organic chemistry
  • Radical chemistry
  • Catalysis

Background:

  • Selective C-H bond functionalization is a key research area.
  • Radical pathways offer efficient C-H functionalization but lack selectivity.
  • Site-selective hydrogen atom abstraction (HAA) remains a significant challenge.

Purpose of the Study:

  • To review recent advances in metal-catalyzed, site-selective C-H bond transformations.
  • To elucidate the role of metal-bound radicals in precise hydrogen abstraction.
  • To highlight novel strategies for regulating radical behavior in targeted functionalization.

Main Methods:

  • Focus on recent literature in metal-catalyzed C-H functionalization.
  • Analysis of mechanisms involving metal-bound radicals.
  • Discussion of strategies for site-selective hydrogen atom abstraction.

Main Results:

  • Metal-bound radicals provide a mechanism for precise HAA.
  • Emerging paradigm offers control over radical selectivity.
  • Enables targeted functionalization of C-H bonds.

Conclusions:

  • Metal catalysis offers a promising approach to overcome selectivity challenges in radical chemistry.
  • This paradigm unlocks new possibilities for selective C-H bond functionalization.
  • Potential for novel radical-mediated transformations in synthetic chemistry.