大学化学 >> 2021, Vol. 36 >> Issue (4): 2004042.doi: 10.3866/PKU.DXHX202004042

知识介绍 上一篇    下一篇

氮杂环卡宾催化的亲核取代反应

赵明(), 杨立庆, 许玉荣   

  • 收稿日期:2020-04-09 录用日期:2020-05-25 发布日期:2020-06-08
  • 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:
    安徽省高校自然科学基金重点项目(KJ2019A0720)

N-Heterocyclic Carbene Catalyzed Nucleophilic Substitution Reaction

Ming Zhao(), Liqing Yang, Yurong Xu   

  • Received:2020-04-09 Accepted:2020-05-25 Published:2020-06-08
  • Contact: Ming Zhao E-mail:zhaomnwu@126.com

摘要:

氮杂环卡宾作为有机催化剂催化的反应取得了巨大的研究进展;在反应中,氮杂环卡宾可以改变醛类化合物的反应极性,由亲电性转变为亲核性。本文主要对氮杂环卡宾催化的亲核取代反应进行了详细介绍,极性反转的醛可以通过SN1、SN2、SN2'、加成-消去、消去-加成过程和相应的底物发生反应。对于醛作为亲核试剂发生的取代反应,能够丰富和完善基础教学中醛酮反应知识点的内容,有利于学生了解学科的前沿发展,激发学生的探索和学习兴趣。

关键词: 氮杂环卡宾, 有机催化, 取代反应,

Abstract:

Great progress has been made in N-heterocyclic carbene (NHC) catalyzed. In the reaction, NHCs are mainly used for the umpolung of aldehydes from electrophilic to nucleophilic. In this paper, the NHC-catalyzed nucleophilic substitution is described in detail; the umpolung of aldehyde and the corresponding substrate react through SN1, SN2, SN2', addition-elimination, elimination-addition processes. The introduction of the substitution reaction of aldehyde as a nucleophile can enrich and extension the content of the knowledge of aldehyde with ketone in undergraduate curriculum. It is also helpful for the students to understand the cutting-edge development of the discipline, and stimulate students' interest in exploration and learning.

Key words: N-Heterocyclic carbene, Organocatalysis, Nucleophilic substitution, Aldehyde

MSC2000: 

  • G64