Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (11): 3944-3952.DOI: 10.6023/cjoc202004041 Previous Articles     Next Articles

Special Issue: 有机光催化虚拟合辑 创刊四十周年专辑


陈亮a,b, 胡良建a,c, 杜宇a, 苏伟平a, 康强a   

  1. a 中国科学院福建物质结构研究所 结构化学国家重点实验室 福州 350002;
    b 中国科学院大学 北京 100049;
    c 福建农林大学材料工程学院 福州 350002
  • 收稿日期:2020-04-25 修回日期:2020-05-14 发布日期:2020-05-20
  • 通讯作者: 苏伟平, 康强,
  • 基金资助:

Asymmetric Photoinduced Giese Radical Addition Enabled by a Single Chiral-at-Metal Rhodium Complex

Chen Lianga,b, Hu Liangjiana,c, Du Yua, Su Weipinga, Kang Qianga   

  1. a State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou 350002;
    b University of Chinese Academy of Sciences, Beijing 100049;
    c College of Material Engineering, Fujian Agriculture and Forestry University, Fuzhou 350002
  • Received:2020-04-25 Revised:2020-05-14 Published:2020-05-20
  • Supported by:
    Project supported by the National Natural Science Foundation of China (No. 21871261).

A visible-light driven asymmetric Giese radical addition catalyzed by a bifunctional chiral-at-metal rhodium complex has been developed. para-Aminobenzyl radicals generated from para-aminophenylacetic acids could undergo a 1,4-addition in a highly enantioselective approach to α,β-unsaturated 2-acyl imidazoles, and a variety of corresponding adducts were obtained in moderate to high yields with excellent enantioselectivities. This reaction features high enantioselectivity, mild reaction conditions and an operationally simple procedure. A plausible reaction mechanism is proposed based on our research and literature precedents on dual functional chiral-at-metal catalysis.

Key words: visible-light photoredox catalysis, bifunctional chiral-at-metal rhodium complex, Giese radical addition, para-aminobenzyl radical