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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 4: 1069 - 1093

DOI: https://doi.org/10.6023/cjoc202308024

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

  • Duyi Shen ,
  • Linghui Li ,
  • Ge Jing ,
  • Yujia Liang ,
  • Xinhui Zhang ,
  • Peiwei Gong ,
  • Fanjun Zhang ,
  • Mianran Chao
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  • 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
* E-mail: ;
;

Received date: 2023-08-27

  Revised date: 2023-11-03

  Online published: 2023-11-15

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

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Abstract

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

Cite this article

Duyi Shen , Linghui Li , Ge Jing , Yujia Liang , Xinhui Zhang , Peiwei Gong , Fanjun Zhang , Mianran Chao . Advances in Flavin-Inspired Photocatalytic Oxidations Involving Single Electron Transfer Process[J]. Chinese Journal of Organic Chemistry, 2024 , 44(4) : 1069 -1093 . DOI: 10.6023/cjoc202308024

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