Chinese Journal of Organic Chemistry ›› 2024, Vol. 44 ›› Issue (4): 1069-1093.DOI: 10.6023/cjoc202308024 Previous Articles     Next Articles

Special Issue: 有机光催化合辑

REVIEWS

基于单电子转移的黄素仿生光催化氧化研究进展

沈都益a,b,*(), 李玲慧a, 靳鸽a, 梁雨佳a, 张欣慧a, 公培伟a, 张范军a,*(), 晁绵冉a,*()   

  1. a 曲阜师范大学化学与化工学院 生命有机分析山东省重点实验室 山东曲阜 273165
    b 中国科学院兰州化学物理研究所 羰基合成与选择氧化国家重点实验室 兰州 730000
  • 收稿日期:2023-08-27 修回日期:2023-11-03 发布日期:2023-11-15
  • 基金资助:
    国家自然科学基金(21802084); 国家自然科学基金(51805295); 国家自然科学基金(51905304); 山东省自然科学基金(ZR2019BB021); 山东省青创团队(2022KJ181); 泰山学者资助项目

Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process

Duyi Shena,b(), Linghui Lia, Ge Jinga, Yujia Lianga, Xinhui Zhanga, Peiwei Gonga, Fanjun Zhanga(), Mianran Chaoa()   

  1. a Key Laboratory of Life-Organic Analysis of Shandong Province, School of Chemistry and Chemical Engineering, Qufu Normal University, Qufu, Shandong 273165
    b State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000
  • Received:2023-08-27 Revised:2023-11-03 Published:2023-11-15
  • Contact: E-mail: shendy@qfnu.edu.cn; chaomr@qfnu.edu.cn; zfjhx@qfnu.edu.cn
  • Supported by:
    National Natural Science Foundation of China(21802084); National Natural Science Foundation of China(51805295); National Natural Science Foundation of China(51905304); Natural Science Foundation of Shandong Province(ZR2019BB021); Shandong Youth Innovation Program for Colleges and Universities(2022KJ181); Funding of Taishan Scholars

Natural flavin coenzymes, featuring simple structure, non-toxicity, and the ability of absorbing and utilizing visible light, frequently act as electron carriers in biological redox reactions. Inspired by the biological function of flavins, great progress has been made in the two-electron oxidation reactions catalyzed by flavins with molecular oxygen or hydrogen peroxide as the terminal oxidant over the past two decades. Due to the versatile and tunable photochemical properties of artificial flavins, in recent years, more and more interests have been drawn to the photoinduced single electron transfer reactions with biomimetic flavins, promoting the rapid developments in the corresponding organic synthetic methodologies. Herein, the advances until July 2023 in bioinspired flavins-catalyzed one-electron oxidation of organic substrates bearing aromatic rings, nitrogen-, oxygen-, and sulfur-based groups under visible-light irradiation, delivering the corresponding radical cations which subsequently take part in the following reactions and enabling various of chemical transformations, are summarized. In addition, selected substrate scopes and possible reaction mechanisms involving single electron transfer process are discussed. Meanwhile, future challenges and opportunities of flavin photocatalysis are also prospected.

Key words: flavin, one-electron oxidation, single electron transfer, radical cation, organic photocatalysis