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Related Concept Videos

Radical Formation: Addition00:47

Radical Formation: Addition

2.4K
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...
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Radical Reactivity: Overview01:11

Radical Reactivity: Overview

3.0K
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...
3.0K
Radical Formation: Overview01:03

Radical Formation: Overview

2.7K
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...
2.7K
Radical Reactivity: Electrophilic Radicals01:02

Radical Reactivity: Electrophilic Radicals

2.6K
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...
2.6K
Radical Reactivity: Intramolecular vs Intermolecular01:33

Radical Reactivity: Intramolecular vs Intermolecular

2.3K
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...
2.3K
Radical Reactivity: Nucleophilic Radicals01:16

Radical Reactivity: Nucleophilic Radicals

2.8K
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...
2.8K

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Energy-Transfer-Mediated Radical-Relay Brook Rearrangement of Electron-Deficient Ketones.

Li-Ning Chen1, Dan-Na Chen1, Lu-Lu Qin1

  • 1School of Chemistry and Pharmaceutical Sciences, Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Ministry of Education of China), Guangxi Key Laboratory of Chemistry and Molecular Engineering of Medicinal Resources, University Engineering Research Center for Chemistry of Characteristic Medicinal Resources (Guangxi), Guangxi Normal University, Guilin 541004, P. R. China.

Organic Letters
|April 16, 2026
PubMed
Summary
This summary is machine-generated.

This study introduces a new photochemical method for synthesizing molecules using energy transfer (EnT)-mediated radical reactions. The process efficiently rearranges ketones and silanes, simplifying complex chemical synthesis.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Radical Chemistry

Background:

  • The Brook rearrangement is a key carbon-carbon bond-forming reaction.
  • Traditional methods often require pre-installed functional groups, limiting substrate scope.
  • Developing new catalytic methods for efficient molecular synthesis is crucial.

Purpose of the Study:

  • To develop a novel energy transfer (EnT)-mediated radical-relay Brook rearrangement.
  • To enable the synthesis of complex molecules from simple starting materials like ketones and silanes.
  • To bypass the need for pre-installed α-silyl groups.

Main Methods:

  • Utilizing an engineered N-O reagent to initiate a radical cascade.
  • Employing silane activation, regioselective carbonyl addition, and radical-radical cross-coupling.
  • Leveraging photochemistry for energy transfer initiation.

Main Results:

  • Successful demonstration of the EnT-mediated radical-relay Brook rearrangement.
  • Broad substrate scope and excellent functional group tolerance observed.
  • Effective late-stage diversification of complex drug molecules achieved.

Conclusions:

  • This protocol offers a new, efficient pathway for the Brook rearrangement.
  • The method simplifies synthetic routes by avoiding pre-installed functional groups.
  • It presents a new paradigm in photochemistry for complex molecule synthesis.