Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton

1,n-Dual Π systems including 1,4-diene derivatives have been widely used as the elegant radical receptors to promote cascade radical additions to give the highly functionalized polycyclic scaffolds. However, the tedious and complicated preparation of the former deters broad utilization and compromises the practical value. Herein, a straightforward preparation of 1,4-diene derivatives was developed from the easily accessible alkynes and γ,δ-unsaturated carboxylic acids via electrochemical oxidation cyclization and Hofmann elimination. This transformation features with good to excellent yields, functional group compatibility, and selectivity without any Zaitsev elimination product detected.

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Publication Details

Journal
iScience
Published
2025-02-10
DOI
https://doi.org/10.1016/j.isci.2025.111976
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton

Zheng Fang, Yaqi Qiao, Chengkou Liu, Chengcheng Yuan et al.
iScience
Radical Photochemical Reactions
article

Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton

Zheng Fang, Yaqi Qiao, Chengkou Liu, Chengcheng Yuan, Xiaoqing Fan
article en

Abstract

1,n-Dual Π systems including 1,4-diene derivatives have been widely used as the elegant radical receptors to promote cascade radical additions to give the highly functionalized polycyclic scaffolds. However, the tedious and complicated preparation of the former deters broad utilization and compromises the practical value. Herein, a straightforward preparation of 1,4-diene derivatives was developed from the easily accessible alkynes and γ,δ-unsaturated carboxylic acids via electrochemical oxidation cyclization and Hofmann elimination. This transformation features with good to excellent yields, functional group compatibility, and selectivity without any Zaitsev elimination product detected.

iScienceVol. 28(3)
Nanjing Tech University (CN)
Government of Jiangsu Province, Natural Science Foundation of Jiangsu Province
Openalex Percentile: Top 98%
Radical Photochemical Reactions
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Electrosynthesis of 1,4-diene derivatives bearing cyclopentene skeleton — Zheng Fang, Yaqi Qiao, et al. · iScience (2025) | TGRS Research Map | TGRS