Metal-Free Radical Azidoarylation of Alkenes: Rapid Access to Oxindoles by Cascade C[BOND]N and C[BOND]C Bond-Forming Reactions

Authors

  • Dr. Kiran Matcha,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
    Search for more papers by this author
  • Dr. Rishikesh Narayan,

    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
    Search for more papers by this author
  • Dr. Andrey P. Antonchick

    Corresponding author
    1. Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
    • Max-Planck-Institut für Molekulare Physiologie, Abteilung Chemische Biologie, Otto-Hahn-Strasse 11, 44227 Dortmund (Germany)
    Search for more papers by this author

  • We thank Prof. Dr. H. Waldmann for generous support.

Abstract

original image

A novel method for the oxidative radical azidation of alkenes relies on an azide in combination with a hypervalent iodine reagent. A cascade of C[BOND]N and C[BOND]C bond-forming reactions yields 2-oxindoles under metal-free conditions with high reaction rates at ambient temperature and provides access to complex products (see scheme; TMS=trimethylsilyl).

Ancillary