University Chemistry ›› 2021, Vol. 36 ›› Issue (4): 2004042.doi: 10.3866/PKU.DXHX202004042

• Survey of Chemistry • Previous Articles     Next Articles

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


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


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