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

Zhi Shang Wang; Dong Guo Hong; Hongfang Li; Teck Peng Loh; Ming Zhu Lu

doi:10.1021/acs.joc.5c00564

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

Zhi Shang Wang, Dong Guo Hong, Hongfang Li, Teck Peng Loh^*, Ming Zhu Lu^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

Abstract

We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-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 Z-selectivity.

Original language	English
Journal	Journal of Organic Chemistry
DOIs	https://doi.org/10.1021/acs.joc.5c00564
Publication status	Accepted/In press - 2025
Externally published	Yes

Bibliographical note

Publisher Copyright:
© 2025 American Chemical Society.

ASJC Scopus Subject Areas

Organic Chemistry

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10.1021/acs.joc.5c00564

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title = "Palladium-Catalyzed Ring-Opening Defluorinative Hiyama Cross-Coupling of gem-Difluorocyclopropanes with Arylsilanes",

abstract = "We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-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 Z-selectivity.",

author = "Wang, {Zhi Shang} and Hong, {Dong Guo} and Hongfang Li and Loh, {Teck Peng} and Lu, {Ming Zhu}",

note = "Publisher Copyright: {\textcopyright} 2025 American Chemical Society.",

year = "2025",

doi = "10.1021/acs.joc.5c00564",

language = "English",

journal = "Journal of Organic Chemistry",

issn = "0022-3263",

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AU - Wang, Zhi Shang

AU - Hong, Dong Guo

AU - Li, Hongfang

AU - Loh, Teck Peng

AU - Lu, Ming Zhu

PY - 2025

Y1 - 2025

N2 - We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-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 Z-selectivity.

AB - We report an efficient palladium-catalyzed ring-opening defluorinative Hiyama cross-coupling of gem-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 Z-selectivity.

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M3 - Article

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SN - 0022-3263

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

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

Abstract

Bibliographical note

ASJC Scopus Subject Areas

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