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Issue 29, 2016
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Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives

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Abstract

An abnormal regioselective substitution of 2-indolylmethanols with nucleophiles such as cyclic enaminone and cyclic anhydride has been established in the presence of Brønsted acid, which efficiently afforded C3-functionalized indole derivatives with structural diversity in high yield and regiospecificity (40 examples, up to 99% yield). Using this approach, the reactivity of the C3-position of the indole was switched from nucleophilic to electrophilic, which could serve as an “umpolung” strategy in organic synthesis.

Graphical abstract: Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives

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Publication details

The article was received on 15 Apr 2016, accepted on 16 Jun 2016 and first published on 16 Jun 2016


Article type: Communication
DOI: 10.1039/C6OB01282E
Org. Biomol. Chem., 2016,14, 6932-6936

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    Brønsted acid-catalyzed regioselective reactions of 2-indolylmethanols with cyclic enaminone and anhydride leading to C3-functionalized indole derivatives

    C. Li, H. Zhang, T. Fan, Y. Shen, Q. Wu and F. Shi, Org. Biomol. Chem., 2016, 14, 6932
    DOI: 10.1039/C6OB01282E

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