Pd-IPent-CatalyzedDefluorinative Annulation of <i>gem</i>-Difluorocyclopropaneswith Enamides: Synthesis of Multisubstituted <i>N</i>‑HPyrroles

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.

Publication Details

Journal
Figshare
Published
2025-02-22
DOI
https://doi.org/10.1021/acs.orglett.5c00241.s001
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Pd-IPent-CatalyzedDefluorinative Annulation of gem-Difluorocyclopropaneswith Enamides: Synthesis of Multisubstituted N‑HPyrroles

Figshare
Fluorine in Organic Chemistry
article

Pd-IPent-CatalyzedDefluorinative Annulation of gem-Difluorocyclopropaneswith Enamides: Synthesis of Multisubstituted N‑HPyrroles

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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.

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Fluorine in Organic Chemistry
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Pd-IPent-CatalyzedDefluorinative Annulation of <i>gem</i>-Difluorocyclopropaneswith Enamides: Synthesis of Multisubstituted <i>N</i>‑HPyrroles · Figshare (2025) | TGRS Research Map | TGRS