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Issue 21, 2016
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Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides

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Abstract

The direct arylation of N-protected 3-haloindole derivatives with benzenesulfonyl chlorides as coupling partners using 5 mol% of bis(acetonitrile)dichloropalladium(II) catalyst and lithium carbonate as a base in 1,4-dioxane was investigated. We demonstrated that both iodo and chloro substituents at the indolyl C3 position act as temporary blocking groups allowing the formation of 2-arylindoles through a direct desulfitative arylation, followed by in situ dehalogenation. While, from 3-bromoindole derivatives, 2-aryl-3-bromoindoles were obtained without debromination, and could be converted into 2,3-diarylindoles through a second palladium coupling. This method allows one to prepare in a few steps a very wide variety of indole derivatives, which are of interest in the synthesis of bioactive molecules.

Graphical abstract: Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides

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Publication details

The article was received on 17 Mar 2016, accepted on 29 Apr 2016 and first published on 02 May 2016


Article type: Paper
DOI: 10.1039/C6OB00584E
Org. Biomol. Chem., 2016,14, 4947-4956

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    Palladium-catalyzed direct desulfitative C2 arylations of 3-halo-N-protected indoles using (hetero)arenesulfonyl chlorides

    A. Hfaiedh, H. Ben Ammar, J. Soulé and H. Doucet, Org. Biomol. Chem., 2016, 14, 4947
    DOI: 10.1039/C6OB00584E

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