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

Chaoqun Ma, Dong Xing* and Wenhao Hu*

*School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai 200062, China, Email: dxingsat.ecnu.edu.cn, whuchem.ecnu.edu.cn

C. Ma, D. Xing, W. Hu, Org. Lett., 2016, 18, 3134-3137.

DOI: 10.1021/acs.orglett.6b01346 (free Supporting Information)


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Abstract

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

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Key Words

oxindoles, NBS


ID: J54-Y2016