Palladium-Catalyzed [4+1] Cycloaddition of 3,3-Difluoropent-4-en-2-ones with Amines: A Modular Approach to 3-Fluoropyrroles

3-Fluoropyrroles are privileged scaffolds in pharmaceutical and agrochemical applications, yet their synthesis remains challenging. Herein, we report a palladium(0)-catalyzed [4+1] cycloaddition/dehydration strategy for the efficient construction of 3-fluoropyrroles from readily available 3,3-difluoropent-4-en-2-ones and primary amines. This transformation proceeds via C-F bond activation to generate a key π-allyl-Pd(II) intermediate, followed by intramolecular addition/dehydration to furnish the heterocyclic core. The method features broad substrate compatibility, mild conditions, and scalability, enabling access to diverse 3-fluoropyrroles that are otherwise difficult to synthesize. This work provides a practical and versatile platform for the discovery of fluorinated pyrrole-based bioactive molecules.

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Publication Details

Journal
Organic Letters
Published
2025-09-04
DOI
https://doi.org/10.1021/acs.orglett.5c02884
Citations
4
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
3.16

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article

Palladium-Catalyzed [4+1] Cycloaddition of 3,3-Difluoropent-4-en-2-ones with Amines: A Modular Approach to 3-Fluoropyrroles

Zhenli Luo, Zhuang Xiong, Jia‐Qiang Wu, Jinhui Hu et al.
4 citations
Organic Letters
Fluorine in Organic Chemistry
3.16
article

Palladium-Catalyzed [4+1] Cycloaddition of 3,3-Difluoropent-4-en-2-ones with Amines: A Modular Approach to 3-Fluoropyrroles

Zhenli Luo, Zhuang Xiong, Jia‐Qiang Wu, Jinhui Hu, Chunming Chen, Mei Xie
article en
4 citations

Abstract

3-Fluoropyrroles are privileged scaffolds in pharmaceutical and agrochemical applications, yet their synthesis remains challenging. Herein, we report a palladium(0)-catalyzed [4+1] cycloaddition/dehydration strategy for the efficient construction of 3-fluoropyrroles from readily available 3,3-difluoropent-4-en-2-ones and primary amines. This transformation proceeds via C-F bond activation to generate a key π-allyl-Pd(II) intermediate, followed by intramolecular addition/dehydration to furnish the heterocyclic core. The method features broad substrate compatibility, mild conditions, and scalability, enabling access to diverse 3-fluoropyrroles that are otherwise difficult to synthesize. This work provides a practical and versatile platform for the discovery of fluorinated pyrrole-based bioactive molecules.

Organic LettersVol. 27(36)
Wuyi University (CN), Wuyi University (CN)
Wuyi University, Basic and Applied Basic Research Foundation of Guangdong Province
Openalex Percentile: Top 8%
Fluorine in Organic Chemistry
3.16
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Palladium-Catalyzed [4+1] Cycloaddition of 3,3-Difluoropent-4-en-2-ones with Amines: A Modular Approach to 3-Fluoropyrroles — Zhenli Luo, Zhuang Xiong, et al. · Organic Letters (2025) | TGRS Research Map | TGRS