有机化学 ›› 2017, Vol. 37 ›› Issue (3): 652-657.DOI: 10.6023/cjoc201610009 上一篇    下一篇

研究论文

镍催化芳基溴化物对羰基的分子内加成反应

张鸣頔, 刘人荣, 高建荣, 贾义霞   

  1. 浙江工业大学化学工程学院 杭州 310014
  • 收稿日期:2016-10-08 修回日期:2016-11-29 发布日期:2016-12-02
  • 通讯作者: 贾义霞,E-mail:yxjia@zjut.edu.cn E-mail:yxjia@zjut.edu.cn
  • 基金资助:

    国家自然科学基金(Nos.21372202,21522207)资助项目.

Nickel-Catalyzed Intramolecular Addition of Aryl Bromides to C=O Bonds

Zhang Mingdi, Liu Renrong, Gao Jianrong, Jia Yixia   

  1. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014
  • Received:2016-10-08 Revised:2016-11-29 Published:2016-12-02
  • Contact: 10.6023/cjoc201610009 E-mail:yxjia@zjut.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (Nos. 21372202, 21522207).

研究了分子内芳基溴化物对羰基的Grignard-类型反应.以Ni(dppe)Br2(10 mmol%)为催化剂,锌粉为还原剂,在乙二醇二甲醚溶剂中分子内溴苯对羰基的亲核加成反应顺利发生,获得3-羟基吲哚啉中间体,该中间体在反应中直接经脱水反应以中等到优异的收率获得一系列吲哚化合物(最高达90%).

关键词: 镍, 加成反应, 芳基溴化物, 脱水反应, 吲哚

A nickel-catalyzed intramolecular Grignard-type addition of aryl bromides to C=O was developed. By using Ni(dppe)Br2 as a catalyst and zinc powder as a reducing agent, the reactions of 2-((2-bromophenyl)amino)-1-arylethanones proceeded smoothly in 1,2-dimethoxyethane solvent to afford 3-hydroxyindolines as intermediates, which underwent dehydration reaction to furnish a range of indole derivatives in moderate to excellent yields (up to 90%).

Key words: nickel, addition reaction, aryl bromide, dehydration reaction, indole