Synthesis of Oxa- and Azapalladacycles from Organostannanes

Authors

  • Diego J. Cárdenas,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid Cantoblanco, E-28049 Madrid (Spain) Telefax: Int. code + (1)397-3966
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  • Cristina Mateo,

    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid Cantoblanco, E-28049 Madrid (Spain) Telefax: Int. code + (1)397-3966
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  • Prof. Antonio M. Echavarren

    Corresponding author
    1. Departamento de Química Orgánica, Universidad Autónoma de Madrid Cantoblanco, E-28049 Madrid (Spain) Telefax: Int. code + (1)397-3966
    • Departamento de Química Orgánica, Universidad Autónoma de Madrid Cantoblanco, E-28049 Madrid (Spain) Telefax: Int. code + (1)397-3966
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  • This work was supported by the DGICYT (project PB91-0612-C03-02). D. J. C. and C. M. acknowledge the receipt of predoctoral fellowships from the Ministerio de Educatión y Ciencia.

Abstract

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An intramolecular Pd–C coupling reaction yields the oxapalladacycle 1. This is the first time that the transmetalation intermediate in the Stille coupling reaction has been isolated. Complexes of type 1 react readily with alkyl, allyl, benzyl, and acyl halides to form aryl-carbon bonds. This reaction can be extended to the preparation of substituted derivatives of 1 and the aza analogue 2.

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