Asymmetric Synthesis of Fluorinated Cyclobutenes Containing Quaternary Carbon Stereocenters by Rh‐Catalyzed Defluoroarylation

Abstract Fluorinated four‐membered rings represent valuable structural motifs in bioactive molecules and pharmaceuticals; however, the asymmetric synthesis of such fluorinated frameworks bearing chiral quaternary carbon centers has not yet been achieved. Herein, we report a Rh‐catalyzed enantioselective defluoroarylation of gem ‐difluorinated cyclobutenes with aryl boronates, enabling the asymmetric construction of fluorinated cyclobutenes bearing chiral quaternary carbon centers with high enantioselectivity via an addition/β‐fluoride elimination process. In situ treatment with an additional distinct aryl boronate enables one‐pot bis‐defluoroarylation to give unsymmetrical diarylated cyclobutenes.

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Publication Details

Journal
Angewandte Chemie
Published
2026-01-04
DOI
https://doi.org/10.1002/ange.202525455
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Asymmetric Synthesis of Fluorinated Cyclobutenes Containing Quaternary Carbon Stereocenters by Rh‐Catalyzed Defluoroarylation

Fushan Yuan, Jie Jia, Jialin Ming, Ying Xia et al.
Angewandte Chemie
Fluorine in Organic Chemistry
article

Asymmetric Synthesis of Fluorinated Cyclobutenes Containing Quaternary Carbon Stereocenters by Rh‐Catalyzed Defluoroarylation

Fushan Yuan, Jie Jia, Jialin Ming, Ying Xia, Xufei Yan, Hui‐Ru Jin
article en

Abstract

Abstract Fluorinated four‐membered rings represent valuable structural motifs in bioactive molecules and pharmaceuticals; however, the asymmetric synthesis of such fluorinated frameworks bearing chiral quaternary carbon centers has not yet been achieved. Herein, we report a Rh‐catalyzed enantioselective defluoroarylation of gem ‐difluorinated cyclobutenes with aryl boronates, enabling the asymmetric construction of fluorinated cyclobutenes bearing chiral quaternary carbon centers with high enantioselectivity via an addition/β‐fluoride elimination process. In situ treatment with an additional distinct aryl boronate enables one‐pot bis‐defluoroarylation to give unsymmetrical diarylated cyclobutenes.

Angewandte ChemieVol. 138(7)
Sichuan University (CN), West China Hospital of Sichuan University (CN), Chengdu University (CN)
Openalex Percentile: Top 97%
Fluorine in Organic Chemistry
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