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化学学报
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化学学报 ›› 2011, Vol. 69 ›› Issue (06): 680-686. 上一篇    下一篇

研究论文

铁催化的苯并异吡喃鎓四氟硼酸盐的氧化自由基偶联行为研究

宋晓男1，莫磊2，胡治隆1，杨震宇1，姚祝军*,1,2   

  1. (1中国科学院上海有机化学研究所生命有机化学国家重点实验室 上海 200032)
    (2南京大学化学化工学院 南京微结构国家实验室(筹) 南京 210093)
  • 投稿日期:2010-09-02 修回日期:2010-10-23 发布日期:2010-12-15
  • 通讯作者: 姚祝军 E-mail:yaoz@sioc.ac.cn
  • 基金资助:

    基金委重点项目;基金委创新群体

Study on Iron-Catalyzed Oxidative Free Radical Dimerization of Isochromenylium Tetrafluoroborate

Song Xiaonan1 Mo Lei2 Hu Zhilong1 Yang Zhenyu1 Yao Zhujun*,1,2   

  1. (1 State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
    (2 Nanjing National Laboratory of Microstructure, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093)
  • Received:2010-09-02 Revised:2010-10-23 Published:2010-12-15
  • Contact: Zhu-Jun Yao E-mail:yaoz@sioc.ac.cn

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苯并异吡喃鎓四氟硼酸盐是新近发现的一类新型有机盐, 具有对空气和潮气的较高稳定性, 同时保持苯并异吡喃鎓盐的高反应活性. 研究了苯并异吡喃鎓四氟硼酸盐在几种铁盐和铁配合物催化剂存在下与过氧化氢之间的氧化反应行为, 发现了一类具有特色的经高价铁物种催化氧化O—H键引发的自由基双分子偶联反应. 本工作对该反应的条件进行了优化研究, 对反应产物和主要副产物的形成机理进行了探讨.

关键词: 苯并异吡喃鎓四氟硼酸盐, 铁, 催化, 氧化反应, 自由基

Isochromenylium tetrafluoroborates (ICTBs) are a novel class of air- and moisture-stable organic salts recently developed by our group. These organic salts retain high reactivity of the unique isochromenylium intermediates in many chemical reactions. The dimerization of ICTBs via O—H bond oxidation with hyper-iron species in the presence of hydrogen peroxide and catalytic amount of iron complex has been studied in this work. Under the optimized conditions, two interesting dimeric products and some minor byproducts were identified, and the corresponding mechanisms were discussed.

Key words: isochromenylium tetrafluoroborate, iron, catalysis, oxidation, free radical