Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (7): 2676-2683.DOI: 10.6023/cjoc202102039 Previous Articles     Next Articles

Special Issue: 有机光催化虚拟合辑



邵子宴, 周庆丽, 王建成, 汤芮, 沈悦海*()   

  1. 昆明理工大学生命科学与技术学院 药学与制药工程中心 昆明 650500
  • 收稿日期:2021-02-22 修回日期:2021-04-02 发布日期:2021-04-29
  • 通讯作者: 沈悦海
  • 基金资助:
    国家自然科学基金(21662022); Ronald J. Quinn AM院士工作站和云南省教育厅高校创新团队(2019IC003)

Sodium Iodide-Triphenylphosphine-Mediated Photoredox Alkylation of Aldimines

Ziyan Shao, Qingli Zhou, Jiancheng Wang, Rui Tang, Yuehai Shen()   

  1. Center for Pharmaceutical Sciences and Engineering, Faculty of Life Science and Technology, Kunming University of Science and Technology, Kunming 650500
  • Received:2021-02-22 Revised:2021-04-02 Published:2021-04-29
  • Contact: Yuehai Shen
  • Supported by:
    National Natural Science Foundation of China(21662022); Ronald J Quinn AM Academician Workstation and the Program for Innovative Research Team (in Science and Technology) in Universities of Yunnan Province(2019IC003)

The photoredox reactions involving electron donor-acceptor (EDA) complexes have attracted significant attentions in the last decade. Very recently, the sodium iodide-triphenylphosphine-N-acyloxyphthalimide EDA complex has been discovered and employed in developing several net redox-neutral photoreactions. Herein, the EDA complex has been applied in a net reductive setup for the first time to establish a photoredox alkylation of aldimines without photosensitizer. The reaction affords not only high yields for secondary, tertiary andα-heterosubstituted alkyl radicals, but also high yields for primary alkyl radicals, and moderate to high yields for electron-rich or secondary benzylic radicals, two difficult groups of radicals in previous studies. This work provides an efficient and reliable approach for the synthesis of unnatural amino acids and amines.

Key words: photoredox, aldimine, electron donor-acceptor complex