Practical C(sp3)–F Bond Construction via Metal-Free Heterogeneous Photodecarboxylative Fluorination in Continuous Flow

We report a robust, metal-free heterogeneous photocatalytic protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids utilizing graphitic carbon nitride (g-C3N4). Operating under visible light, this strategy exhibits good substrate generality, particularly for activated aliphatic carboxylic acids and facilitates the late-stage functionalization of complex pharmaceutical scaffolds. The operationally simple photocatalyst can be recycled over seven consecutive cycles while maintaining high catalytic efficacy. Crucially, a continuous-flow, gram-scale synthesis validates its practical scalability. Mechanistic studies confirm a closed-loop photoredox pathway, establishing a versatile platform for C(sp3)-F bond construction.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-10-13
DOI
https://doi.org/10.1021/acs.joc.6c01769
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Practical C(sp3)–F Bond Construction via Metal-Free Heterogeneous Photodecarboxylative Fluorination in Continuous Flow

Dingfeng Yang, Caiwen Wan, Yuanyuan Li, Jie Gao et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Practical C(sp3)–F Bond Construction via Metal-Free Heterogeneous Photodecarboxylative Fluorination in Continuous Flow

Dingfeng Yang, Caiwen Wan, Yuanyuan Li, Jie Gao, Junwen Shu, Ruolan Leng, Changtong Shao, Yexuan Luo, Zhangyi Ran, Yingjie Zhu
article en

Abstract

We report a robust, metal-free heterogeneous photocatalytic protocol for the direct decarboxylative fluorination of aliphatic carboxylic acids utilizing graphitic carbon nitride (g-C3N4). Operating under visible light, this strategy exhibits good substrate generality, particularly for activated aliphatic carboxylic acids and facilitates the late-stage functionalization of complex pharmaceutical scaffolds. The operationally simple photocatalyst can be recycled over seven consecutive cycles while maintaining high catalytic efficacy. Crucially, a continuous-flow, gram-scale synthesis validates its practical scalability. Mechanistic studies confirm a closed-loop photoredox pathway, establishing a versatile platform for C(sp3)-F bond construction.

The Journal of Organic Chemistry
Chongqing University of Education (CN)
National Natural Science Foundation of China, Chongqing Municipal Education Commission, Chongqing University of Education
Openalex Percentile: Top 25%
Radical Photochemical Reactions
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