Palladium-Catalyzed Intramolecular Hydroarylation of N-Alkynylindoles: Regioselective Synthesis of Indole-Annulated Sulfur/Phosphorus Heterocycles

As privileged structural motifs, the efficient synthesis of multifused N-heterocycles remains highly challenging. Here, we report a palladium-catalyzed intramolecular hydroarylation of N-alkynyl indoles bearing an electron-withdrawing group at the 2-position. This reaction proceeds in high yield (up to 95%) and excellent regioselectivity, producing six-membered, indole-annulated sulfur/phosphorus heterocycles. This method offers a robust and efficient protocol for constructing these valuable scaffolds.

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Publication Details

Journal
Organic Letters
Published
2025-12-02
DOI
https://doi.org/10.1021/acs.orglett.5c04356
Primary Topic
Sulfur-Based Synthesis Techniques
Type
article
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article

Palladium-Catalyzed Intramolecular Hydroarylation of N-Alkynylindoles: Regioselective Synthesis of Indole-Annulated Sulfur/Phosphorus Heterocycles

Boxin Zhang, Zhijin Fan, Shun-Han Yang, Haitao Yu et al.
Organic Letters
Sulfur-Based Synthesis Techniques
article

Palladium-Catalyzed Intramolecular Hydroarylation of N-Alkynylindoles: Regioselective Synthesis of Indole-Annulated Sulfur/Phosphorus Heterocycles

Boxin Zhang, Zhijin Fan, Shun-Han Yang, Haitao Yu, Yanmei Li, Yunlong Zhao, Xinlu Li, Ye Wang
article en

Abstract

As privileged structural motifs, the efficient synthesis of multifused N-heterocycles remains highly challenging. Here, we report a palladium-catalyzed intramolecular hydroarylation of N-alkynyl indoles bearing an electron-withdrawing group at the 2-position. This reaction proceeds in high yield (up to 95%) and excellent regioselectivity, producing six-membered, indole-annulated sulfur/phosphorus heterocycles. This method offers a robust and efficient protocol for constructing these valuable scaffolds.

Organic LettersVol. 27(49)
Laboratoire de Synthèse Organique (FR), Hebei Normal University (CN)
Openalex Percentile: Top 71%
Sulfur-Based Synthesis Techniques
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