α-Olefination of Nitriles: Base-Promoted Ring-Opening Coupling of Nitriles and Chromone

A new strategy for base-promoted ring-opening coupling reaction between nitriles and chromones for the synthesis of α-olefins was developed. This method demonstrates significant advantages, including high atomic economy, metal-free, air atmosphere, solvent-free, and room-temperature conditions. In this transformation process, the base promotes the progress of the Michael-type addition reaction, thereby initiating a ring-opening reaction between chromone and nitrile molecules. Two distinct types of α-olefination pathways for nitriles have been successfully established using a wide range of nitrile substrates. Most α-alkenylated products demonstrate notable antioxidant activity, revealing their potential applications in antioxidant development and promising prospects for pharmaceutical research.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-10-21
DOI
https://doi.org/10.1021/acs.joc.5c01471
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

α-Olefination of Nitriles: Base-Promoted Ring-Opening Coupling of Nitriles and Chromone

Tao Sheng, Zhi‐Hong Du, Bin Dai, Min Li et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

α-Olefination of Nitriles: Base-Promoted Ring-Opening Coupling of Nitriles and Chromone

Tao Sheng, Zhi‐Hong Du, Bin Dai, Min Li, Ning Liu, Chun-Bo Bo, Fei Chen, Tao Wang, Di Wu, Jieying Tang
article en

Abstract

A new strategy for base-promoted ring-opening coupling reaction between nitriles and chromones for the synthesis of α-olefins was developed. This method demonstrates significant advantages, including high atomic economy, metal-free, air atmosphere, solvent-free, and room-temperature conditions. In this transformation process, the base promotes the progress of the Michael-type addition reaction, thereby initiating a ring-opening reaction between chromone and nitrile molecules. Two distinct types of α-olefination pathways for nitriles have been successfully established using a wide range of nitrile substrates. Most α-alkenylated products demonstrate notable antioxidant activity, revealing their potential applications in antioxidant development and promising prospects for pharmaceutical research.

The Journal of Organic ChemistryVol. 90(46)
Shihezi University (CN), Shaoyang University (CN)
Openalex Percentile: Top 77%
Catalytic C–H Functionalization Methods
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