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PdII-Catalyzed C[BOND]H Olefination of N-(2-Pyridyl)sulfonyl Anilines and Arylalkylamines

Authors

  • Alfonso García-Rubia,

    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
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  • Beatriz Urones,

    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
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  • Dr. Ramón Gómez Arrayás,

    Corresponding author
    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
    • Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
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  • Prof. Dr. Juan C. Carretero

    Corresponding author
    1. Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
    • Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid (UAM), Cantoblanco 28049 Madrid (Spain)
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  • This work was supported by the Ministerio de Ciencia e Innovación (MICINN; projects CTQ2006-01121 and CTQ2009-07791) and the Consejería de Educación de la Comunidad de Madrid (programme AVANCAT; S2009/PPQ-1634). A.G.-R. and B.U. thank the MICINN for a predoctoral fellowship. We also thank Johnson Matthey PLC for a generous supply of Pd(OAc)2.

Abstract

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Flexible friend: The N-(2-pyridyl)sulfonyl group acts as a removable directing group in the PdII-catalyzed aryl C[BOND]H ortho alkenylation of N-alkyl aniline, benzylamine, and phenethylamine derivatives with electron-poor alkenes. The products were obtained in high yields (70–90 %) and with complete regiocontrol. The mild reductive N-sulfonyl removal enables the construction of a variety of nitrogen heterocycles. EWG=electron-withdrawing group.

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