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Updated: Oct 9, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Radical Reactions of Ynamides
Tong-De Tan1, Ze-Shu Wang1, Peng-Cheng Qian2
1Key Laboratory for Chemical Biology of Fujian Province & State Key Laboratory of Physical Chemistry of Solid Surfaces, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China.
This review summarizes radical reactions involving ynamides (alkynes tethered to an amide group), focusing on their reactivity at the alpha and beta positions. It highlights advances in selectivity, scope, and mechanisms for these underutilized synthetic transformations.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Reaction Mechanisms
Background:
- Ynamides, electron-rich alkynes linked to an amide, are versatile synthetic reagents.
- While ionic reactions of ynamides are well-established, radical-based reactions remain less explored.
Purpose of the Study:
- To comprehensively review the advances in radical reactions of ynamides.
- To categorize these reactions based on the site of radical attack (α- or β-position).
- To illuminate future directions in ynamide chemistry.
Main Methods:
- Literature review of radical reactions involving ynamides.
- Classification of reactions by radical attack position.
- Analysis of reaction selectivity, scope, mechanism, and applicability.
Main Results:
- Detailed summary of known radical ynamide reactions.
- Discussion on factors influencing reaction selectivity and outcomes.
- Identification of key mechanistic pathways.
Conclusions:
- Radical reactions of ynamides offer unique synthetic opportunities.
- Further research into radical ynamide chemistry is warranted.
- This review provides a foundation for developing novel synthetic methodologies.
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