Chemoselective Electrochemical Synthesis of 3-Hydroxyisoindolinones from Phthalimide Imines

We report an electrochemical method for the radical-radical coupling of alkyl iodides with phthalimide imines under mild conditions. This operationally simple electro-reductive procedure enables selective reduction of carbonyl groups, offering an efficient route to access functionalized 3-hydroxyisoindolinones in moderate-to-excellent yields. Notably, the highly functionalized 3-hydroxyisoindolinones have shown promising bioactivity in preliminary assessments, pointing to the significant potential of this chemical scaffold for anticancer cell applications. A comparative analysis has demonstrated that the hydrazone moiety within the product structure plays an indispensable role in conferring bioactivity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-14
DOI
https://doi.org/10.1021/acs.joc.6c01017
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Chemoselective Electrochemical Synthesis of 3-Hydroxyisoindolinones from Phthalimide Imines

Zenghui Ye, Xi Zhang, Jian‐Xing Xu, Yicai Li et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Chemoselective Electrochemical Synthesis of 3-Hydroxyisoindolinones from Phthalimide Imines

Zenghui Ye, Xi Zhang, Jian‐Xing Xu, Yicai Li, Wei-Yuan Ma, Qiaohong Xu, Fengzhi Zhang
article en

Abstract

We report an electrochemical method for the radical-radical coupling of alkyl iodides with phthalimide imines under mild conditions. This operationally simple electro-reductive procedure enables selective reduction of carbonyl groups, offering an efficient route to access functionalized 3-hydroxyisoindolinones in moderate-to-excellent yields. Notably, the highly functionalized 3-hydroxyisoindolinones have shown promising bioactivity in preliminary assessments, pointing to the significant potential of this chemical scaffold for anticancer cell applications. A comparative analysis has demonstrated that the hydrazone moiety within the product structure plays an indispensable role in conferring bioactivity.

The Journal of Organic Chemistry
Hangzhou Medical College (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 26%
Radical Photochemical Reactions
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