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Issue 51, 2017
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Metal-free formal carbon–halogen bond insertion: facile syntheses of 3-halo 3,3′-disubstituted oxindoles and spirooxindole-γ-butyrolactones

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Abstract

A novel P(NMe2)3-mediated formal carbon–halogen bond insertion of isatins into allylic and benzylic bromides/chlorides has been realized, leading to a facile synthesis of 3-halo 3,3′-disubstituted oxindoles. This reaction relies on the unique dual nucleophilic–electrophilic reactivity pattern of the Kukhtin–Ramirez adduct via a cascade SN2–SN2 process. It also represents a rare metal-free approach for carbon–halogen bond insertion. Upon treatment with trifluoroacetic acid, spirooxindole-γ-butyrolactones have been efficiently prepared from the corresponding insertion products.

Graphical abstract: Metal-free formal carbon–halogen bond insertion: facile syntheses of 3-halo 3,3′-disubstituted oxindoles and spirooxindole-γ-butyrolactones

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Publication details

The article was received on 15 May 2017, accepted on 29 May 2017 and first published on 31 May 2017


Article type: Communication
DOI: 10.1039/C7CC03765A
Citation: Chem. Commun., 2017,53, 6860-6863
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    Metal-free formal carbon–halogen bond insertion: facile syntheses of 3-halo 3,3′-disubstituted oxindoles and spirooxindole-γ-butyrolactones

    R. Zhou, R. Liu, K. Zhang, L. Han, H. Zhang, W. Gao and R. Li, Chem. Commun., 2017, 53, 6860
    DOI: 10.1039/C7CC03765A

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