Construction of a Pentacyclic Framework Enabled by Nickel Catalysis

We present a novel nickel-catalyzed reaction of indole-tethered 2-alkynylphenol esters with various (hetero)­aryl boronic acids, resulting in the synthesis of diversely functionalized pentacyclic benzofurocyclohepta­[b]­indole derivatives. This unprecedented cascade reaction involves the arylative c...

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Bibliographic Details
Published in:Organic letters 2023-02, Vol.25 (4), p.647-652
Main Authors: Iqbal, Naeem, Ashraf, Muhammad Awais, Gul, Anam Rana, Bae, Jaehan, Iqbal, Naila, Park, Tae Jung, Cho, Eun Jin
Format: Article
Language:English
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Summary:We present a novel nickel-catalyzed reaction of indole-tethered 2-alkynylphenol esters with various (hetero)­aryl boronic acids, resulting in the synthesis of diversely functionalized pentacyclic benzofurocyclohepta­[b]­indole derivatives. This unprecedented cascade reaction involves the arylative cyclization of alkynes, nucleophilic attack of the indole moiety on the oxonium ion intermediate, 1,2-alkyl group migration, and aromatization. The synthesized molecules exhibit exceptional cytotoxicity against multiple cancer cell lines while maintaining biocompatibility toward healthy cells.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c04228