有机化学 ›› 2022, Vol. 42 ›› Issue (3): 796-802.DOI: 10.6023/cjoc202109026 上一篇    下一篇

研究论文

可回收铋配合物催化氮亲核试剂与对醌甲基化物1,6-加成:轻松获得N-杂环取代的不对称三芳基甲烷衍生物

刘冬兰, 许海燕*(), 杭懿, 陆鸿飞*()   

  1. 江苏科技大学环境与化学工程学院 江苏镇江 212100
  • 收稿日期:2021-09-17 修回日期:2021-11-08 发布日期:2021-11-25
  • 通讯作者: 许海燕, 陆鸿飞
  • 作者简介:
    † 共同第一作者
  • 基金资助:
    国家自然科学基金(21901087); 江苏省自然科学基金(BK20190591)

1,6-Addition of Nitrogen Nucleophile to para-Quinone Methides Catalyzed by Recyclable Bismuth Complex: Facile Access to N-Heterocyclic Substituted Unsymmetric Triarylmethane Derivatives

Donglan Liu, Haiyan Xu(), Yi Hang, Hongfei Lu()   

  1. School of Environmental and Chemical Engineering, Jiangsu University of Science and Technology, Zhenjiang, Jiangsu 212100
  • Received:2021-09-17 Revised:2021-11-08 Published:2021-11-25
  • Contact: Haiyan Xu, Hongfei Lu
  • About author:
    † These authors contributed equally to this work.
  • Supported by:
    National Natural Science Foundation of China(21901087); Natural Science Foundation of Jiangsu Province(BK20190591)

开发了一种用对醌甲基化物(p-QMs)和各种芳香族N-杂环化合物1,6-氮杂-迈克尔加成合成含氮不对称三芳基甲烷衍生物的方法. 这种合成方法具有反应条件温和、催化剂负载量可接受、原子经济性、易于放大的特点, 并且能够以中等至优异的产率形成N-杂环取代的不对称三芳基甲烷衍生物. 此外, 铋催化剂可以重复使用多次而不会损失其活性.

关键词: 可回收的铋催化剂, N-杂环取代的不对称三芳基甲烷衍生物, 对醌甲基化物, 1,6-迈克尔加成反应

A useful protocol for the synthesis of nitrogen-containing unsymmetric triarylmethane derivatives through 1,6-aza-Michael addition of para-quinone methides (p-QMs) and various aromatic N-heterocycles was developed. This established synthetic strategy features mild reaction conditions, acceptable catalyst loading, atom economy, easy scale-up and enables the formation of N-heterocyclic-substituted unsymmetric triarylmethane derivatives in moderate to excellent yields. Moreover, the bismuth catalyst can be reused several times without losing of its activity.

Key words: recyclable bismuth catalyst, N-heterocyclic-substituted unsymmetric triarylmethane derivatives, para-quinone methide, 1,6-Michael addition reaction