Construction of 2-Fluoroallylsilanes by Palladium-Catalyzed Ring-Opening Defluorinative Silylation of <i>gem</i> -Difluorocyclopropanes

Herein, we report a palladium-catalyzed ring-opening defluorinative silylation strategy for the efficient one-step synthesis of 2-fluoroallylsilanes. This method employs readily available aryl <i>gem</i>-difluorocyclopropanes as fluorine-containing building blocks, enabling the direct construction of fluorinated allylsilane scaffolds through selective C-C bond insertion followed by β-fluoride elimination/silylation. The reaction employs 10% Pd(OAc)<sub>2</sub> as the catalyst and 15% X-Phos as the ligand, demonstrating broad functional group compatibility. Compared with previously reported methods, this protocol features readily available starting materials and operational simplicity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-23
DOI
https://doi.org/10.1021/acs.joc.5c02056
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Construction of 2-Fluoroallylsilanes by Palladium-Catalyzed Ring-Opening Defluorinative Silylation of gem -Difluorocyclopropanes

Chengqiang Ge, Haidong Liu, Yupeng Qian, Xuan Zhu et al.
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
article

Construction of 2-Fluoroallylsilanes by Palladium-Catalyzed Ring-Opening Defluorinative Silylation of gem -Difluorocyclopropanes

Chengqiang Ge, Haidong Liu, Yupeng Qian, Xuan Zhu, Haiqing Luo, Shujuan Huang
article en

Abstract

Herein, we report a palladium-catalyzed ring-opening defluorinative silylation strategy for the efficient one-step synthesis of 2-fluoroallylsilanes. This method employs readily available aryl <i>gem</i>-difluorocyclopropanes as fluorine-containing building blocks, enabling the direct construction of fluorinated allylsilane scaffolds through selective C-C bond insertion followed by β-fluoride elimination/silylation. The reaction employs 10% Pd(OAc)<sub>2</sub> as the catalyst and 15% X-Phos as the ligand, demonstrating broad functional group compatibility. Compared with previously reported methods, this protocol features readily available starting materials and operational simplicity.

The Journal of Organic ChemistryVol. 91(1)
Gannan Medical University (CN), Gannan Normal University (CN)
Openalex Percentile: Top 38%
Fluorine in Organic Chemistry
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