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

详细信息    查看全文

• 作者：Chaoqun Ma ; Dong Xing ; Wenhao Hu
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：July 1, 2016
• 年：2016
• 卷：18
• 期：13
• 页码：3134-3137
• 全文大小：335K
• 年卷期：0
• ISSN：1523-7052

文摘

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.