Defluorinative Alkene-Carbonyl Coupling Enabled by Photoredox Catalysis: An Access to Allylic Alcohols

The defluorinative coupling of fluoroalkenes with carbonyl compounds provides a direct and efficient strategy to valuable allylic alcohols. However, existing methods typically rely on transition-metal catalyst, stoichiometric reductants, or strongly reducing conditions. Herein, we report a photoredox catalyzed defluorinative coupling between fluoroalkenes and aliphatic carbonyls mediated by ligated boryl radicals, enabling the synthesis of both fluorinated and nonfluorinated allylic alcohols dictated by the choice of fluoroalkene substrate. This transition-metal-free protocol operates under mild conditions, exhibiting high <i>Z</i>/<i>E</i> stereoselectivity and broad substrate scope.

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Publication Details

Journal
Organic Letters
Published
2025-12-20
DOI
https://doi.org/10.1021/acs.orglett.5c04919
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79
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article

Defluorinative Alkene-Carbonyl Coupling Enabled by Photoredox Catalysis: An Access to Allylic Alcohols

Qing‐Xiao Tong, Yonghong Xiao, Xi Wang, Tingting Miao et al.
1 citations
Organic Letters
Fluorine in Organic Chemistry
0.79
article

Defluorinative Alkene-Carbonyl Coupling Enabled by Photoredox Catalysis: An Access to Allylic Alcohols

Qing‐Xiao Tong, Yonghong Xiao, Xi Wang, Tingting Miao, Rong‐Bin Liang, Jian‐Ji Zhong
article en
1 citations

Abstract

The defluorinative coupling of fluoroalkenes with carbonyl compounds provides a direct and efficient strategy to valuable allylic alcohols. However, existing methods typically rely on transition-metal catalyst, stoichiometric reductants, or strongly reducing conditions. Herein, we report a photoredox catalyzed defluorinative coupling between fluoroalkenes and aliphatic carbonyls mediated by ligated boryl radicals, enabling the synthesis of both fluorinated and nonfluorinated allylic alcohols dictated by the choice of fluoroalkene substrate. This transition-metal-free protocol operates under mild conditions, exhibiting high <i>Z</i>/<i>E</i> stereoselectivity and broad substrate scope.

Organic LettersVol. 28(1)
Shantou University (CN), Key Laboratory of Guangdong Province (CN)
Openalex Percentile: Top 20%
Fluorine in Organic Chemistry
0.79
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