大学化学 >> 2022, Vol. 37 >> Issue (6): 2108056.doi: 10.3866/PKU.DXHX202108056

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氮杂环卡宾催化的Michael加成反应

赵明(), 许玉荣, 林静, 陈虎   

  • 收稿日期:2021-08-17 录用日期:2021-09-07 发布日期:2021-10-27
  • 通讯作者: 赵明 E-mail:zhaomnwu@126.com
  • 作者简介:赵明, Email: zhaomnwu@126.com
  • 基金资助:
    安徽省自然科学基金青年项目(1908085QE172);安徽省自然科学基金青年项目(2008085QC99)

N-Heterocyclic Carbene Catalyzed Michael Addition Reaction

Ming Zhao(), Yurong Xu, Jing Lin, Hu Chen   

  • Received:2021-08-17 Accepted:2021-09-07 Published:2021-10-27
  • Contact: Ming Zhao E-mail:zhaomnwu@126.com

摘要:

Michael加成反应是有机化学中的重要反应,作为有机催化剂的氮杂环卡宾也能够催化Michael加成反应。本文主要对氮杂环卡宾催化的Michael加成反应进行了详细介绍,氮杂环卡宾可以和醛进行结合,形成具有亲核性的Breslow中间体,醛的反应极性由亲电性转变为亲核性,极性反转的醛与αβ-不饱和酮、酯等Michael受体发生加成反应,即Stetter反应;氮杂环卡宾也可以作为Brønsted碱,活化醇等发生Michael加成反应。对于氮杂环卡宾催化的Michael加成反应的介绍,能够丰富和拓展基础教学中Michael加成反应知识点的内容,有利于学生了解学科的前沿发展,激发学生的学习兴趣。

关键词: 氮杂环卡宾, Michael加成, 有机催化, Brønsted碱

Abstract:

The Michael addition is an important reaction in organic chemistry, and N-heterocyclic carbene (NHC) can also catalyze the Michael addition as an organic catalyst. In this paper, the NHC-catalyzed Michael addition is described in detail, addition of the NHC to the aldehyde forms the Breslow intermediate with nucleophilicity, aldehydes undergo the umpolung from electrophilic to nucleophilic and react with the Michael acceptor. The NHC can also be used as Brønsted base to activate alcohols and undergo Michael addition reactions. The introduction of NHC-catalyzed Michael addition can enrich and extension the content of the Michael addition in undergraduate curriculum. It is also helpful for the students to understand the cutting-edge development of the discipline and stimulate students' interests in learning.

Key words: N-Heterocyclic carbene, Michael addition, Organocatalysis, Brønsted base

MSC2000: 

  • G64