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Palladium-catalyzed regioselective C–H alkynylation of indoles with bromoalkynes in water

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Abstract

A highly regioselective alkynylation of indoles has been accomplished for the assembly of functionalized C2 alkynylindoles in moderate to good yields with a primary amine as the directing group. This protocol represents an efficient palladium-catalyzed C(sp2)–H activation/alkynylation using water/aqueous media as a sustainable solvent. Moreover, the scalability was demonstrated and further transformations of the alkynylating products were achieved, demonstrating the potential applications in synthetic and pharmaceutical chemistry. Preliminary mechanistic investigations suggest that the cleavage of the C2 C–H bond of indoles is likely to be the rate-determining step in this reaction.

Graphical abstract: Palladium-catalyzed regioselective C–H alkynylation of indoles with bromoalkynes in water

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Publication details

The article was received on 20 Nov 2018, accepted on 03 Jan 2019 and first published on 04 Jan 2019


Article type: Research Article
DOI: 10.1039/C8QO01261J
Citation: Org. Chem. Front., 2019, Advance Article

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    Palladium-catalyzed regioselective C–H alkynylation of indoles with bromoalkynes in water

    W. Wu, S. Fang, G. Jiang, M. Li and H. Jiang, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C8QO01261J

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