基于单电子转移的黄素仿生光催化氧化研究进展

doi:10.6023/cjoc202308024

有机化学 ›› 2024, Vol. 44 ›› Issue (4): 1069-1093.DOI: 10.6023/cjoc202308024 上一篇下一篇

所属专题：有机光催化合辑

综述与进展

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

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摘要/Abstract

自然界的黄素辅酶具有结构简单、无毒、能吸收和利用可见光等特点, 常常作为电子载体参与生物体内的氧化还原反应. 受黄素催化氧化功能的启发, 过去二十年里, 黄素衍生物催化以氧气或双氧水为终端氧化剂的两电子氧化反应得到了长足发展; 而近年来, 由于黄素衍生物丰富易调控的光化学性质, 更多的注意力开始转向它们所促进的单电子转移反应, 相应的有机合成方法学也正在涌现. 综述了截止到2023年7月的可见光驱动黄素衍生物催化诸如芳香环、含氮、含氧及含硫等官能团的单电子氧化, 生成相应的阳离子自由基中间体再参与后续过程来实现多样化有机转化的相关进展. 同时, 对底物范围和单电子转移机理进行了讨论, 并对该领域的未来发展进行了展望.

关键词: 黄素, 单电子氧化, 单电子转移, 自由基阳离子, 有机光催化

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

引用此文

沈都益, 李玲慧, 靳鸽, 梁雨佳, 张欣慧, 公培伟, 张范军, 晁绵冉. 基于单电子转移的黄素仿生光催化氧化研究进展[J]. 有机化学, 2024, 44(4): 1069-1093.

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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图/表 37

图1. 代表性的天然黄素及其仿生光催化剂

Figure 1. Representative natural flavins and their biomimetic photocatalysts

图式1. 黄素的氧化还原和酸碱平衡性质

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

图式2. 黄素光催化需氧氧化三种典型模式

Scheme 2. Three typical modes of flavin photocatalytic aerobic oxidation

图式3. 黄素衍生物及其镁配合物促进苄醇单电子氧化机理

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

图2. 四乙酰化核黄素与钪离子的配位模式

Figure 2. Binding mode of Sc3+ to RFT

图式4. 钪和盐酸共同促进RFT光催化苄位C—H需氧氧化

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

图式5. 盐酸辅助RFT光催化芳香缩醛单电子氧化

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

图3. Cibulka课题组报道的黄素盐和中性黄素分子

Figure 3. Flaviniums and flavins of Cibulka?s group

图式6. 光诱导黄素盐催化甲苯需氧氧化成羧酸

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

图式7. 基态和激发态下仿生脱氮黄素盐氧化还原性质

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

图式8. 以乙腈为电子受体的脱氮黄素光催化苄醇氧化

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

图式9. K?nig等提出的RFT光催化二苯乙烯和二苯乙炔需氧氧化反应机理

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

图式10. 黄素氮氧化物与脱氧黄素的反应活性

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

图式11. RFT-Sc3+光催化炔烃区域选择性氧化官能化反应

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

图式12. 光诱导RFT-Sc3+催化炔烃氧化官能化反应可能的机理

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

图式13. 光诱导RFT催化N-保护芳香胺和苯酚的硝化反应

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

图式14. 光诱导RFT催化N-Boc苯胺硝化反应机理

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

图式15. 光黄素催化吲哚单电子氧化及C(3)烷基化反应

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

图式16. 短肽桥联的黄素-胺杂化体分子内电子转移

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

图式17. RFT光催化醛和胺氧化偶联制备三级酰胺

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

图式18. RFT光催化醛和胺氧化偶联制备酰胺的机理

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

图式19. 光驱动RFT催化α,β-烯酮需氧环氧化

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

图式20. 光驱动RFT催化烯酮环氧化可能的机理

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

图式21. 核黄素四丁酸酯催化位点选择性脱羧-加成反应

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

图式22. 光驱动核黄素催化邻苯基苯甲酸氧化-分子内偶联

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

图式23. 光诱导RFT催化脂肪酸脱羧-氰化反应

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

图式24. 光诱导RFT催化脂肪酸脱羧-氰化反应可能的机理

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

图式25. 光诱导RFT催化脂肪酸脱羧-烯丙基化反应

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

图式26. 蓝光促进FMN催化Fmoc-氨基酸脱羧-氧化

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

图式27. 蓝光诱导FMN催化酚氧化去芳构化反应

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

图式28. 基于单电子转移途径的黄素光催化硫醚氧化

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

图式29. RFT光催化硫代酰胺环化合成2-取代苯并噻唑

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

图式30. 光驱动RFT作为Lewis酸催化醛合成硫缩酮

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

图式31. 黄素光催化甲硫氨酸残基选择性官能化

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

图式32. 三苯膦介导和黄素光催化酸醇酯化反应机理

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

图式33. 光黄素催化以及水活化的有机硼酸脱硼烷基化

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

图式34. 光黄素催化水活化的有机硼酸脱硼烷基化反应机理

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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