光电联合催化的研究进展

doi:10.6023/cjoc202106051

摘要/Abstract

近年来, 温和、绿色的光化学和电化学反应在有机合成中得到了广泛的应用. 为了进一步提升光、电反应潜力, 有机化学家们致力于在单一反应体系中使用这两种策略来促进有机转化. 一系列光电联合催化策略被开发出来, 目前主要的光电联合催化策略是电化学介导的光氧化还原催化. 此外, 光激发辅助、电化学主导氧化还原的光电联合催化策略也逐渐展现出其在有机合成中的潜力. 这些策略实现了光化学与电化学优缺点的互补, 能解决光化学和电化学所不能解决的部分问题, 如去除使反应复杂化的氧化还原剂, 在温和的条件下生成活性高的中间体等. 按照现有的光电联合催化反应, 分类总结光电联合催化策略的研究进展, 并探讨了部分反应可能的机理.

关键词: 光氧化还原催化, 电催化, 光电化学

Photochemical and electrochemical reactions, which are mild and green, have been widely used in organic synthesis in recent years. To push the limits of both synthetic technologies, organic chemists have focused on using these two strategies to promote organic transformation in a single reaction system. A series of photoelectrochemical strategies have been developed, and the main one at present is electrochemically mediated photoredox catalysis. In addition, photoexcitation-assisted electroredox strategies have also gradually shown their potential in organic synthesis. These strategies realize the complementary advantages and disadvantages of photochemistry and electrochemistry, and can solve the problems that can not be solved by a single synthetic technology, such as removing oxidizing reducing agents that complicate the reaction, generating intermediates with high activity under mild conditions, and so on. In this paper, the research progress of photoelectrochemical strategies is summarized according to the existing photoelectric catalysis reactions, and the possible mechanism of some reactions is discussed.

Key words: photoredox catalysis, electrocatalysis, photoelectrochemistry

引用此文

刘颖杰, 王智传, 孟建萍, 李晨, 孙凯. 光电联合催化的研究进展[J]. 有机化学, 2022, 42(1): 100-110.

Yingjie Liu, Zhichuan Wang, Jianping Meng, Chen Li, Kai Sun. Research Progress of Photoelectric Co-catalysis[J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 100-110.

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图/表 28

图1. 电化学反应示意图

Figure 1. Schematic diagram of electrochemical reaction

图2. 光催化循环

Figure 2. Photocatalytic cycle

图3. 光电催化

Figure 3. Photoelectrocatalysis

图式1. 光电催化下芳烃C―H的三氟甲基化反应

Scheme 1. Trifluoromethylation of aromatic hydrocarbon C―H under photoelectric catalysis

图式2. 光电催化下C―H杂芳烃与有机三氟硼酸盐的烷基化反应

Scheme 2. Alkylation of C―H heteroaromatics with organic trifluoroborate under photoelectric catalysis

图式3. 4-甲基喹啉光电催化下氮邻位的烷基化反应机理

Scheme 3. Alkylation mechanism of nitrogen ortho-position under photoelectric catalysis of 4-methylquinoline

图式4. 杂环芳烃与羧酸和草酸的光电脱羧C―H烷基化和氨基甲酰化反应

Scheme 4. Photoelectric decarboxylation of heterocyclic aromatic hydrocarbons with carboxylic and oxalic acids by C―H alkylation and carbamylation

图式5. 杂环芳烃与草酸烷基的C―H烷基化反应

Scheme 5. C―H alkylation of heterocyclic aromatic hydrocarbons with alkyl oxalate

图式6. 光电催化下C(sp3)―H键叠氮化反应

Scheme 6. Photoelectrocatalytic azide reaction of C(sp3)―H bond

图式7. 光电催化下C(sp3)―H键的叠氮化反应机理

Scheme 7. Azidation mechanism of C(sp3)―H bond under photoelectric catalysis

图式8. RFT和TU共催化醇的光电反应

Scheme 8. Photoelectric reaction of alcohol co-catalyzed by RFT and TU

图式9. RFT和TU共催化醇的光电反应机理

Scheme 9. Photoelectric reaction mechanism of alcohol co- catalyzed by RFT and TU

图式10. 苯并噻唑与脂肪族供氢体的脱氢交叉偶联反应

Scheme 10. Dehydrogenation cross-coupling of benzothiazole with aliphatic hydrogen donors

图式11. 电光催化芳烃C―H唑化反应

Scheme 11. Electrophotocatalytic C―H azolation of aromatic hydrocarbons

图式12. 芳烃和氮杂芳烃的电光催化偶联

Scheme 12. Electrophotocatalytic coupling of arenes and nitrogen heteroaromatics

图式13. 光电催化下苯和1H-吡唑-4-羧酸乙酯的C―H/N―H偶联反应机理

Scheme 13. C―H/N―H coupling reaction mechanism of benzene and 1H-pyrazole-4-ethyl carboxylate under photoelectric catalysis

图式14. 未活化芳基氟化物的电光催化芳香族亲核取代反应

Scheme 14. Electrophotocatalytic SNAr of unactivated aryl fluorides

图式15. 光电催化下醚邻位的C-C和C-N偶联反应

Scheme 15. C-C and C-N coupling reactions of ether ortho sites under photoelectric catalysis

图式16. 光电催化下3,4-二氢咪唑的合成

Scheme 16. Electrophotocatalytic synthesis of 3,4-dihydro- imidazole

图式17. 光电催化下2-噁唑啉的合成

Scheme 17. Electrophotocatalytic synthesis of 2-oxazoline

图式18. 芳基卤化物的光电催化硼化反应

Scheme 18. Photoelectrocatalytic borylation of aryl halides

图式19. 芳基卤化物光电催化生成芳基自由基反应机理

Scheme 19. Reaction mechanism of aryl radical generation by photoelectric catalysis of aryl halides

图式20. 芳基氯光电催化磷酸化反应

Scheme 20. Photoelectrocatalytic phosphorylation of aryl chloride

图式21. 烯烃的光电催化氮丙啶化反应

Scheme 21. Photoelectrocatalytic aziridination of olefin

图式22. 烯烃的光电催化氮丙啶化反应机理

Scheme 22. Mechanism of photoelectrocatalytic aziridination of olefin

图式23. 碘化物介导的C―H胺化反应

Scheme 23. C―H amination mediated by iodide

图式24. 碘化物介导的C―H胺化反应机理

Scheme 24. Reaction mechanism of iodide-mediated C―H amination

图式25. 杂芳烃和C(sp3)―H供体的脱氢交叉偶联反应

Scheme 25. Dehydrogenation cross-coupling of heteroaromatics with C(sp3)―H donors

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