Photoinduced Charge-Transfer Complex Enables ortho-Fluorobenzamide C–F Bond Activation in Isoindolinone Synthesis

Abstract Photoinduced reactions of o-iodo, o-bromo, and o-chlorobenzamides have been well-established for the synthesis of isoindolinones; however, the corresponding fluorinated substrates remain underexplored. Herein, we report the photoactivation of fluorobenzamides via a novel charge-transfer complex (CTC) pathway, enabling the efficient synthesis of isoindolinone derivatives. Central to this approach is the formation of a CTC between the tBuOK/DMSO anion and fluorobenzamides under light irradiation. This method is operationally simple, mild, and provides a practical route for accessing isoindolinones.

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Publication Details

Journal
Synthesis
Published
2026-01-02
DOI
https://doi.org/10.1055/a-2773-5408
Primary Topic
Synthesis and pharmacology of benzodiazepine derivatives
Type
article
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article

Photoinduced Charge-Transfer Complex Enables ortho-Fluorobenzamide C–F Bond Activation in Isoindolinone Synthesis

He Sheng, Xiang-Yu Chen, Xin Zhang
Synthesis
Synthesis and pharmacology of benzodiazepine derivatives
article

Photoinduced Charge-Transfer Complex Enables ortho-Fluorobenzamide C–F Bond Activation in Isoindolinone Synthesis

He Sheng, Xiang-Yu Chen, Xin Zhang
article en

Abstract

Abstract Photoinduced reactions of o-iodo, o-bromo, and o-chlorobenzamides have been well-established for the synthesis of isoindolinones; however, the corresponding fluorinated substrates remain underexplored. Herein, we report the photoactivation of fluorobenzamides via a novel charge-transfer complex (CTC) pathway, enabling the efficient synthesis of isoindolinone derivatives. Central to this approach is the formation of a CTC between the tBuOK/DMSO anion and fluorobenzamides under light irradiation. This method is operationally simple, mild, and provides a practical route for accessing isoindolinones.

SynthesisVol. 58(06)
University of Chinese Academy of Sciences (CN)
Openalex Percentile: Top 99%
Synthesis and pharmacology of benzodiazepine derivatives
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