Sc(OTf)<sub>3</sub>-Catalyzed Construction of Fused Bisindolylmethanes: Unified Access to 1,2- and 1,7-Linked Indole Frameworks

We report a concise, efficient, and scalable synthetic strategy for the construction of fused bisindolylmethanes (BIMs) via Sc(OTf)<sub>3</sub>-catalyzed Friedel-Crafts cyclization of <i>N</i>-alkyl acetal indoles. This protocol enables regioselective access to both 1,2- and previously unexplored 1,7-fused BIMs under mild and operationally simple conditions. The transformation demonstrates broad substrate tolerance and excellent functional group compatibility, delivering structurally diverse fused indole architectures with potential relevance in medicinal chemistry, complex molecule synthesis, and late-stage peptide modification.

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Publication Details

Journal
Organic Letters
Published
2025-09-30
DOI
https://doi.org/10.1021/acs.orglett.5c03698
Primary Topic
Synthesis of Indole Derivatives
Type
article
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article

Sc(OTf)3-Catalyzed Construction of Fused Bisindolylmethanes: Unified Access to 1,2- and 1,7-Linked Indole Frameworks

Xiaomeng Gong, Ruipeng Li, Kang Dong, Shouchu Tang et al.
Organic Letters
Synthesis of Indole Derivatives
article

Sc(OTf)3-Catalyzed Construction of Fused Bisindolylmethanes: Unified Access to 1,2- and 1,7-Linked Indole Frameworks

Xiaomeng Gong, Ruipeng Li, Kang Dong, Shouchu Tang, Long Peng, Huiwen Yang, Weiwei Zhang
article en

Abstract

We report a concise, efficient, and scalable synthetic strategy for the construction of fused bisindolylmethanes (BIMs) via Sc(OTf)<sub>3</sub>-catalyzed Friedel-Crafts cyclization of <i>N</i>-alkyl acetal indoles. This protocol enables regioselective access to both 1,2- and previously unexplored 1,7-fused BIMs under mild and operationally simple conditions. The transformation demonstrates broad substrate tolerance and excellent functional group compatibility, delivering structurally diverse fused indole architectures with potential relevance in medicinal chemistry, complex molecule synthesis, and late-stage peptide modification.

Organic LettersVol. 27(40)
Sichuan University (CN), West China Hospital of Sichuan University (CN), Ningxia Medical University (CN), Nature Conservation Agency (LV), Lanzhou University (CN)
Openalex Percentile: Top 80%
Synthesis of Indole Derivatives
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