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

doi:10.6023/cjoc202308024

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

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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^,^*()

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 Shen^a^,^b(), Linghui Li^a, Ge Jing^a, Yujia Liang^a, Xinhui Zhang^a, Peiwei Gong^a, Fanjun Zhang^a(), Mianran Chao^a()

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

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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.

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Fig. & Tab. 37

Figure 1. Representative natural flavins and their biomimetic photocatalysts

Scheme 1. Redox behavior and acid-base equilibrium of flavins

Scheme 2. Three typical modes of flavin photocatalytic aerobic oxidation

Scheme 3. Proposed mechanism for the one-electron oxidation of benzyl alcohol by flavin-Mg2+ complex

Figure 2. Binding mode of Sc3+ to RFT

Scheme 4. Catalytic aerobic oxidation of benzylic C—H bonds by RFT with the aid of both Sc3+ and HCl

Scheme 5. HCl-assisted photocatalytic one-electron oxidation of aromatic acetal enabled by RFT

Figure 3. Flaviniums and flavins of Cibulka?s group

Scheme 6. Visible-light-induced aerobic oxidation of toluene to carboxylic acid enabled by flavinium

Scheme 7. Redox property of a bioinspired deazaflavinium at the ground and excited states

Scheme 8. Oxidation of benzyl alcohol by deazaflavinium photocatalyst with MeCN as the electron acceptor

Scheme 9. Proposed mechanism for RFT-catalyzed aerobic oxidation of stilbene and tolane under photo irradiation by Konig et al.

Scheme 10. Reactivity of flavin N-oxide and the corresponding deoxyflavin

Scheme 11. Regioselective oxyfunctionalization of alkynes with a RFT-Sc3+ photocatalytic system

Scheme 12. Proposed mechanism of the oxyfunctionalization of alkynes enabled by a RFT-Sc3+ photocatalytic system

Scheme 13. Nitration of N-protected aromatic amine and phenol enabled by RFT photocatalyst

Scheme 14. Mechanism of nitration of N-Boc aniline enabled by RFT photocatalyst

Scheme 15. One-electron oxidation and C(3)-alkylation of indole with LF as the photocatalyst

Scheme 16. Proposed intramolecular electron transfer of a peptide-bridged flavin-amine hybrid

Scheme 17. Tertiary amide formation by aerobic oxidative coupling of aldehydes and amines via RFT photocatalysis

Scheme 18. Mechanism of tertiary amide preparation via photooxidative coupling of aldehydes and amines

Scheme 19. Photo-driven and RFT-catalyzed aerobic epoxidation of α,β-enone

Scheme 20. Possible mechanism for the photo-driven and RFT-catalyzed epoxidation of enone

Scheme 21. Site-selective decarboxylative-addition enabled by RFTB photocatalysis

Scheme 22. Intramolecular oxidative coupling of ortho-phenyl benzoic aicd with RF as the photocatalyst

Scheme 23. Decarboxylative cyanation of aliphatic carboxylic acids catalyzed by RFT under photo irradiation

Scheme 24. Mechanism of decarboxylative cyanation of aliphatic carboxylic acids catalyzed by RFT under photo irradiation

Scheme 25. Photocatalytic decarboxylative allylation of aliphatic carboxylic acids enabled by RFT

Scheme 26. FMN-catalyzed decarboxylative oxidation of fluorenyl-modified amino acids under blue light

Scheme 27. FMN-catalyzed oxidative dearomatization of orcinaldehyde under blue light irradiation

Scheme 28. Oxidation of sulfide enabled by flavin photocatalysts via single electron transfer

Scheme 29. Synthesis of 2?substituted benzothiazoles via the cyclization of thiobenzanilides enabled by RFT photocatalysis

Scheme 30. Thioacetalization of aldehyde using RFT as a Lewis acid catalyst under photo irradiation

Scheme 31. Site-selective functionalization of methionine residues enabled by LF photocatalysis

Scheme 32. Mechanism of PPh3-mediated and flavin-catalyzed esterification of acid and alcohol

Scheme 33. LF-catalyzed deborylative-alkylation of boronic acids activated by water

Scheme 34. Mechanism for the LF-catalyzed deborylative-alkylation of boronic acids activated by water

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基于单电子转移的黄素仿生光催化氧化研究进展

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

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