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.
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.
Chaoqun
C
Ma
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.
Dong
D
Xing
Shanghai Engineering Research Center of Molecular Therapeutics and New Drug Development, School of Chemistry and Molecular Engineering, East China Normal University , 3663 North Zhongshan Road, Shanghai 200062, China.
Wenhao
W
Hu