Pd-IPent-Catalyzed Defluorinative Annulation of <i>gem</i>-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted <i>N</i>-H Pyrroles

We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of <i>gem</i>-difluorocyclopropanes with enamides, which provides a convenient and efficient strategy for the synthesis of multisubstituted <i>N</i>-H pyrrole derivatives. This transformation selectively cleaves the C<sub>1</sub>-C<sub>3</sub> bond, two C-F bonds, and the C-N bond in a one-pot procedure. Additionally, this protocol allows for the modification of several bioactive molecules.

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Publication Details

Journal
Organic Letters
Published
2025-02-21
DOI
https://doi.org/10.1021/acs.orglett.5c00241
Citations
7
Primary Topic
Fluorine in Organic Chemistry
Type
article
Field-Weighted Citation Impact
5.54

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article

Pd-IPent-Catalyzed Defluorinative Annulation of gem-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted N-H Pyrroles

Leiyang Lv, Jiping Sheng, Wenhao Liu, Zhiping Li et al.
7 citations
Organic Letters
Fluorine in Organic Chemistry
5.54
article

Pd-IPent-Catalyzed Defluorinative Annulation of gem-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted N-H Pyrroles

Leiyang Lv, Jiping Sheng, Wenhao Liu, Zhiping Li, Yahui Ma, Qiuwei Huang
article en
7 citations

Abstract

We present a Pd-IPent-catalyzed ring-opening defluorinative annulation reaction of <i>gem</i>-difluorocyclopropanes with enamides, which provides a convenient and efficient strategy for the synthesis of multisubstituted <i>N</i>-H pyrrole derivatives. This transformation selectively cleaves the C<sub>1</sub>-C<sub>3</sub> bond, two C-F bonds, and the C-N bond in a one-pot procedure. Additionally, this protocol allows for the modification of several bioactive molecules.

Organic LettersVol. 27(9)
Renmin University of China (CN)
National Natural Science Foundation of China, Renmin University of China, Beijing Municipal Natural Science Foundation, Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 5%
Fluorine in Organic Chemistry
5.54
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Pd-IPent-Catalyzed Defluorinative Annulation of <i>gem</i>-Difluorocyclopropanes with Enamides: Synthesis of Multisubstituted <i>N</i>-H Pyrroles — Leiyang Lv, Jiping Sheng, et al. · Organic Letters (2025) | TGRS Research Map | TGRS