Metal- and Photosensitizer-Free Radical Strategy for the Construction of Fluorinated Oxiranes

Abstract Fluorinated oxiranes are valuable structural motifs in medicinal chemistry and materials science, yet their synthesis remains challenging due to the limited availability of efficient and general methods. Herein, we disclose a photoinduced radical epoxidation strategy that enables the direct construction of diverse fluorinated oxiranes from readily available fluoroalkyl halides and allylic peroxides without transition metals, photocatalysts, or external oxidants. This mild and oxidant-free protocol exhibits broad functional-group tolerance and accommodates a variety of bioactive molecules, natural-product derivatives, and pharmaceutical scaffolds, enabling the late-stage functionalization of complex molecules.

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Publication Details

Journal
Organic Letters
Published
2026-10-07
DOI
https://doi.org/10.1021/acs.orglett.6c03640
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
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article

Metal- and Photosensitizer-Free Radical Strategy for the Construction of Fluorinated Oxiranes

Jiang Duan, Chao Shu, Shuaiqi Lu, Zhenzhen Li et al.
Organic Letters
Radical Photochemical Reactions
article

Metal- and Photosensitizer-Free Radical Strategy for the Construction of Fluorinated Oxiranes

Jiang Duan, Chao Shu, Shuaiqi Lu, Zhenzhen Li, Zhengjun He, Yidong Shen, Hui Xu
article en

Abstract

Abstract Fluorinated oxiranes are valuable structural motifs in medicinal chemistry and materials science, yet their synthesis remains challenging due to the limited availability of efficient and general methods. Herein, we disclose a photoinduced radical epoxidation strategy that enables the direct construction of diverse fluorinated oxiranes from readily available fluoroalkyl halides and allylic peroxides without transition metals, photocatalysts, or external oxidants. This mild and oxidant-free protocol exhibits broad functional-group tolerance and accommodates a variety of bioactive molecules, natural-product derivatives, and pharmaceutical scaffolds, enabling the late-stage functionalization of complex molecules.

Organic Letters
Central China Normal University (CN)
Openalex Percentile: Top 25%
Radical Photochemical Reactions
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