Catalyst-Free Halogenation of α-Diazocarbonyl Compounds with N-Halosuccinimides: Synthesis of 3-Halooxindoles or Vinyl Halides

A novel catalyst-free halogenative cyclization of N-aryl diazoamides with N-halosuccinimides (NXS) is reported for the synthesis of 3-halooxindoles through a carbene-free mechanism. N-Aryl diazoamides reacted with NXS under mild and catalyst-free conditions to afford the corresponding 3-halooxindoles in good yields. This transformation is proposed to proceed through diazonium ion formation followed by intramolecular Friedel-Crafts alkylation.