Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of <i>gem</i>-Difluorocyclopropanes with Arylsilanes

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of <i>gem</i>-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F bond cleavage. This regioselective ring-opening defluorinative Hiyama cross-coupling features a broad substrate scope with excellent functional group compatibility, affording a diverse variety of linear 2-fluoroallylic scaffolds in good yields with high <i>Z</i>-selectivity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-04-18
DOI
https://doi.org/10.1021/acs.joc.5c00564
Citations
4
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
3.16

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article

Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes

Hongfang Li, Teck‐Peng Loh, Zimin Wang, Mingzhu Lu et al.
4 citations
The Journal of Organic Chemistry
Fluorine in Organic Chemistry
3.16
article

Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes

Hongfang Li, Teck‐Peng Loh, Zimin Wang, Mingzhu Lu, Daniel C. Hong
article en
4 citations

Abstract

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of <i>gem</i>-difluorocyclopropanes with structurally diverse (hetero)arylsilanes through C-C bond activation and C-F bond cleavage. This regioselective ring-opening defluorinative Hiyama cross-coupling features a broad substrate scope with excellent functional group compatibility, affording a diverse variety of linear 2-fluoroallylic scaffolds in good yields with high <i>Z</i>-selectivity.

The Journal of Organic ChemistryVol. 90(17)
Nanyang Technological University (SG), Henan University of Technology (CN), Huaiyin Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 9%
Fluorine in Organic Chemistry
3.16
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Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of <i>gem</i>-Difluorocyclopropanes with Arylsilanes — Hongfang Li, Teck‐Peng Loh, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS