Synthesis of Indoles via Electron-Catalyzed Intramolecular C–N Bond Formation

A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C–N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number of substrates, indoles were afforded in yields...

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Bibliographic Details
Published in:Organic letters 2018-12, Vol.20 (23), p.7358-7362
Main Authors: Bugaenko, Dmitry I, Dubrovina, Anastasia A, Yurovskaya, Marina A, Karchava, Alexander V
Format: Article
Language:English
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Summary:A new protocol for the preparation of N-substituted indole-3-carboxylates has been developed. The key C–N bond formation occurs under transition-metal-free conditions employing a t-BuOK/DMF system without special initiators or additives. Across a number of substrates, indoles were afforded in yields higher or comparable to those obtained under transition-metal-catalyzed conditions. While demonstrating high functional group tolerance, new conditions are particularly attractive for manufacturing halogenated indoles that cannot be made in a pure form using other metal-based catalytic methods.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.8b02784