高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (4): 719-724.doi: 10.7503/cjcu20180610

• 有机化学 • 上一篇    下一篇

B(C6F5)3催化吲哚与苯乙炔的区域选择性加成

刘天伟, 张苏韬, 何江华, 张越涛   

  1. 吉林大学化学学院, 超分子结构与材料国家重点实验室, 长春 130012
  • 收稿日期:2018-08-30 出版日期:2019-04-10 发布日期:2019-01-15
  • 通讯作者: 何江华,女,博士,副教授,主要从事生物质降解以及有机合成方法学方面的研究.E-mail:hjh2015@jlu.edu.cn E-mail:hjh2015@jlu.edu.cn
  • 基金资助:
    国家自然科学基金(批准号:21871107,21774042)资助.

Metal-free B(C6F5)3 Catalyzed Regioselective Addition of Indole to Phenylacetylene

LIU Tianwei, ZHANG Sutao, HE Jianghua, ZHANG Yuetao   

  1. State Key Laboratory of Supramolecular Structure and Materials, College of Chemistry, Jilin University, Changchun 130012, China
  • Received:2018-08-30 Online:2019-04-10 Published:2019-01-15
  • Supported by:
    Supported by the National Natural Science Foundation of China (Nos.21871107,21774042).

摘要: 使用B(C6F53替代稀有金属催化剂,实现了绿色、无毒、温和催化吲哚与苯乙炔的加成反应.对吲哚不同位置带有取代基的底物进行拓展,在室温条件下高产率获得了一系列双吲哚烷烃.对机理的初步探究表明,反应首先从苯乙炔被B(C6F53活化开始,而后依次受到两分子吲哚进攻,经马氏加成得到相应产物.根据探究结果,给出了可能的反应机理.

关键词: B(C6F5)3, 吲哚, 选择性加成, 双吲哚烷烃

Abstract: Catalytic amounts of B (C6F5)3 was found to be able to catalyze the highly regioselective addition of various indoles to phenylacetylene,and produced different substituted bisindolylmethanes in high yields at room temperature.Contrast to the traditional catalysts such as In,Pt and Ru,B (C6F5)3 finished the reaction under green and mild catalytic conditions with high atom economical and good functional group tolerance.Under the optimization reaction conditions,near quantitative conversions and up to 92% yields of bisindolylmethanes were achieved.According to the separated byproduct 4a' and the observed intermediates Ⅰ,a possible reaction mechanism based on the mechanistic studies has been proposed.The reaction was initiated from the activation of phenylacetylene by B (C6F5)3 and ended with the addition of two molecules indoles one by one to the phenylacetylene.The further applied value research of bisindolylmethanes is in progress.

Key words: B(C6F5)3, Indole, Regioselective addition, Bisindolylalkanes

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