Acta Chimica Sinica ›› 2023, Vol. 81 ›› Issue (10): 1271-1279.DOI: 10.6023/A23060268 Previous Articles     Next Articles

Special Issue: 庆祝《化学学报》创刊90周年合辑

Original article


孟庆端,a,b, 韩佳宏,a,b, 潘一骁a, 郝伟a,b,*(), 范青华a,b,*()   

  1. a 中国科学院化学研究所 中国科学院分子识别与功能重点实验室 北京分子科学国家研究中心 北京 100190
    b 中国科学院大学 北京 100049
  • 投稿日期:2023-06-02 发布日期:2023-07-06
  • 作者简介:
  • 基金资助:
    国家重点研发计划(2021YFA1500200); 国家自然科学基金(92056108); 国家自然科学基金(92256303)

Asymmetric Synthesis of C1-Symmetric Chiral N-Heterocyclic Carbene (NHC) Ligands and Their Applications in Asymmetric Catalysis

Qingduan Meng,a,b, Jiahong Han,a,b, Yixiao Pana, Wei Haoa,b(), Qing-Hua Fana,b()   

  1. a Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190
    b University of Chinese Academy of Sciences, Beijing 100049
  • Received:2023-06-02 Published:2023-07-06
  • Contact: *E-mail:;
  • About author:
    Dedicated to the 90th anniversary of Acta Chimica Sinica.
    These authors contributed equally to this work
  • Supported by:
    National Key R&D Program of China(2021YFA1500200); National Natural Science Foundation of China(92056108); National Natural Science Foundation of China(92256303)

A class of C1-symmetric chiral N-heterocyclic carbene (NHC) ligands, incorporating both chiral fused-ring and sterically hindered N-substituted groups, were designed and synthesized, with the asymmetric reductive amination of quinoline aldehyde with arylamine compounds as the key step. Subsequently, using palladium-catalyzed intramolecular α-arylation and copper-catalyzed protoboration of functionalization of alkenes as the model reactions, the relationship between the structure of these ligands and their catalytic performance was systematically investigated. It was found that the 8-substituted groups on the tetrahydroquinoline scaffold and the bulky chiral N-substituted groups played important roles in enhancing the chiral induction ability of the ligands.

Key words: chiral N-heterocyclic carbene ligand, asymmetric catalysis, Pd catalysis, Cu catalysis, reductive amination