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Updated: Jun 17, 2026
10:44
Isolating Free Carbenes, their Mixed Dimers and Organic Radicals
Published on: April 19, 2019
Chalcogen σ-hole interaction enabled radical reactions
Yan Zhang1, Jin-Ru Chen1, Xiang-Yu Chen2,3
1School of Chemistry and Chemical Engineering, Shandong University of Technology, 266 West Xincun Road, Zibo 255049, China. qiangliu@sdut.edu.cn.
Chemical Communications (Cambridge, England)
|June 16, 2026
Summary
Chalcogen bonding (ChB) activates chemical reactions via σ-hole interactions. This review explores ChB-enabled radical reactions, showcasing mild, metal-free conditions for novel synthetic pathways.
Area of Science:
- Chemistry
- Organic Chemistry
- Supramolecular Chemistry
Background:
- Chalcogen bonding (ChB) is a noncovalent interaction involving Group 16 elements.
- ChB has emerged as a significant activation strategy in synthetic chemistry.
- Radical reactions are fundamental in organic synthesis.
Purpose of the Study:
- To provide a comprehensive overview of Chalcogen bonding-enabled radical reactions.
- To highlight the use of ChB interactions for unprecedented reactivity under mild conditions.
- To explore mechanistic themes in ChB-driven radical chemistry.
Main Methods:
- Review of existing literature on Chalcogen bonding and radical reactions.
- Categorization of ChB-enabled radical reactions into cationic and neutral mechanisms.
- Analysis of mechanistic insights from spectroscopic, computational, and radical-trapping studies.
Main Results:
- ChB interactions facilitate radical generation under mild, transition metal-free, and photocatalyst-free conditions.
- Cationic ChB involves sulfonium and selenonium salts forming photoactive complexes.
- Neutral ChB plays a critical role in orchestrating single-electron transfer processes.
Conclusions:
- Chalcogen bonding offers a tunable and versatile platform for radical generation.
- ChB-enabled radical reactions unlock novel synthetic possibilities.
- Future applications include asymmetric catalysis, multicatalytic networks, and continuous-flow synthesis.
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