Nickel-Catalyzed Reductive Arylation of <i>gem</i>-Bromofluorocyclopropanes To Construct Monofluorinated Cyclopropane Derivatives

A nickel-catalyzed reductive cross-coupling of <i>gem</i>-bromofluorocyclopropanes with aryl bromides for the synthesis of monofluorinated cyclopropane derivatives is reported. Different from the cleavage route of the cyclopropane ring reported by previous works, this catalytic system shows excellent regioselectivity control of cyclic selectivity, giving monofluorinated cyclopropane derivatives as the major product. This transformation demonstrates mild conditions, high efficiency, a broad substrate scope, and good functional group compatibility, providing a facile method for the synthesis of diversified monofluorinated cyclopropane-containing drugs and bioactive molecules.

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Publication Details

Journal
Organic Letters
Published
2025-03-19
DOI
https://doi.org/10.1021/acs.orglett.5c00665
Citations
1
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
0.79

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article

Nickel-Catalyzed Reductive Arylation of gem-Bromofluorocyclopropanes To Construct Monofluorinated Cyclopropane Derivatives

Xi‐Sheng Wang, Tian-Rui Wu, Wen Zhang, Shi Chen et al.
1 citations
Organic Letters
Fluorine in Organic Chemistry
0.79
article

Nickel-Catalyzed Reductive Arylation of gem-Bromofluorocyclopropanes To Construct Monofluorinated Cyclopropane Derivatives

Xi‐Sheng Wang, Tian-Rui Wu, Wen Zhang, Shi Chen, Yuheng Huang, Bingbing Wu, Hong-Rui Yuan
article en
1 citations

Abstract

A nickel-catalyzed reductive cross-coupling of <i>gem</i>-bromofluorocyclopropanes with aryl bromides for the synthesis of monofluorinated cyclopropane derivatives is reported. Different from the cleavage route of the cyclopropane ring reported by previous works, this catalytic system shows excellent regioselectivity control of cyclic selectivity, giving monofluorinated cyclopropane derivatives as the major product. This transformation demonstrates mild conditions, high efficiency, a broad substrate scope, and good functional group compatibility, providing a facile method for the synthesis of diversified monofluorinated cyclopropane-containing drugs and bioactive molecules.

Organic LettersVol. 27(12)
University of Science and Technology of China (CN), Guizhou University (CN), Hefei National Center for Physical Sciences at Nanoscale (CN)
National Natural Science Foundation of China, National Key Research and Development Program of China
Openalex Percentile: Top 30%
Fluorine in Organic Chemistry
0.79
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Nickel-Catalyzed Reductive Arylation of <i>gem</i>-Bromofluorocyclopropanes To Construct Monofluorinated Cyclopropane Derivatives — Xi‐Sheng Wang, Tian-Rui Wu, et al. · Organic Letters (2025) | TGRS Research Map | TGRS