Cu-Mediated Tandem 2,3-Disubstituted Indole Synthesis from Simple Anilines and Internal Alkynes via C–H Annulation

A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds has been developed. The present protocol involves copper-mediated tandem hydroamination followed by C–H annulation of unprotected anilines with a wide range of internal alkynes. In the presen...

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Bibliographic Details
Published in:Journal of organic chemistry 2023-08, Vol.88 (15), p.10960-10973
Main Authors: Jagtap, Prafull A., Lokolkar, Manjunath S., Bhanage, Bhalchandra M.
Format: Article
Language:English
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Summary:A simple, cost-effective, and straightforward method for the synthesis of 2,3-disubstituted indole scaffolds has been developed. The present protocol involves copper-mediated tandem hydroamination followed by C–H annulation of unprotected anilines with a wide range of internal alkynes. In the presence of Cu­(OAc)2·H2O and trifluoroacetic acid (TFA), the reaction proceeds well to afford a variety of substituted indole derivatives in moderate to good yields. This process was found to be compatible with both primary and secondary anilines coupled with aromatic/aliphatic alkynes. High-purity copper nanoparticles can be recovered after the reaction, revealing the cost-effectiveness and environmentally benign feature of the current protocol.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c00954