Synthesis of <i>meta</i>-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides

A copper(II)-catalyzed radical cascade reaction of <i>N</i>-propargyl enamides with sulfonyl hydrazides was developed, which provided an unprecedented method for the direct synthesis of <i>meta</i>-sulfonylpyridines in high efficiency with good functional group compatibility and simple operation. Mechanistic studies indicated that this tandem process might be composed of the radical addition, intramolecular cyclization and oxidative aromatization.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-05
DOI
https://doi.org/10.1021/acs.joc.5c00140
Citations
1
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
Field-Weighted Citation Impact
0.94

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article

Synthesis of meta-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides

Jinchun Chen, Xin‐Ming Xu, Yuhang Yao, Qian Liu et al.
1 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
0.94
article

Synthesis of meta-Sulfonylpyridines via Copper(II)-Catalyzed Cascade Sulfonylation/Cyclization/Aromatization of Tertiary Enamides with Sulfonylhydrazides

Jinchun Chen, Xin‐Ming Xu, Yuhang Yao, Qian Liu, Zhongyuan Zhao, Jiping Wang, Xiaoxu Chen, Lu Shao
article en
1 citations

Abstract

A copper(II)-catalyzed radical cascade reaction of <i>N</i>-propargyl enamides with sulfonyl hydrazides was developed, which provided an unprecedented method for the direct synthesis of <i>meta</i>-sulfonylpyridines in high efficiency with good functional group compatibility and simple operation. Mechanistic studies indicated that this tandem process might be composed of the radical addition, intramolecular cyclization and oxidative aromatization.

The Journal of Organic ChemistryVol. 90(10)
Yantai University (CN)
Yantai University, National Natural Science Foundation of China, Natural Science Foundation of Shandong Province
Openalex Percentile: Top 28%
Sulfur-Based Synthesis Techniques
0.94
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