光电化学金属催化研究进展

doi:10.6023/cjoc202409038

摘要/Abstract

光电化学金属催化融合了光化学、电化学以及金属催化的特性, 为高活性自由基的可控产生及选择性转化提供了新的研究思路. 光催化剂可以在电极表面得失电子形成相应的光敏剂, 避免传统光化学合成中等物质的量的氧化还原试剂的使用; 体系中的金属催化剂既可以作为电化学催化剂在电极表面上传递电子, 还可以和反应底物相互作用, 控制反应的路径. 这种新型的催化策略同时利用光能和电能作为反应的驱动力, 极大地降低了反应的电极电势, 从而在温和的条件下完成常规方法难以实现的电子转移活化过程. 总结了过去几年光电化学金属催化领域取得的重要研究进展, 通过选取的典型示例以及相关的反应机理解读展示该方法的合成特点及优势.

关键词: 光电化学催化, 过渡金属, 氧化还原, 自由基

Electrophotochemical transition metal catalysis integrates the characteristics of photochemistry, electrochemistry, and transition metal catalysis, providing an elegant approach for selective generation and transformation of highly reactive radical species in synthetic chemistry. Photoredox catalysts can gain or lose electrons on the electrode surface to form the corresponding photosensitizers, avoiding the use of stoichiometric redox reagents in traditional photochemical reactions. The metal catalysts in the system can both act as electrocatalysts to transfer electrons between electrodes and substrates, and interact with substrates to control the reaction pathways. This novel catalytic strategy harnesses both light and electrical energy as the driving force for the reaction, substantially reducing the electrode potential and enabling electron transfer activation processes that are commonly challenging to achieve under otherwise mild conditions. The research progress of this new field of research in the past few years is summarized, and the prospects of further developments are also discussed.

Key words: electrophotocatalysis, transition metal, redox, radical

引用此文

姚嫣, 付年凯. 光电化学金属催化研究进展[J]. 有机化学, 2025, 45(6): 1819-1837.

Yan Yao, Niankai Fu. Recent Advances in Electrophotochemical Transition Metal Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(6): 1819-1837.

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图/表 24

图式1. 早期光电化学催化的氧化反应探索

Scheme 1. Early examples of electrophotocatalysis in oxidation reactions

图1. 电化学氧化实现光催化剂的重生

Figure 1. Electrochemical oxidation enabled regeneration of photoredox catalyst

图2. 电化学氧化生成光催化剂

Figure 2. Electrochemical oxidation generated photoredox catalyst

图3. 电化学还原生成光催化剂

Figure 3. Electrochemical reduction generated photoredox catalyst

图4. 光电化学催化的C—H键三氟甲基化反应

Figure 4. Electrophotocatalytic C—H trifluoromethylation

图5. 光电化学催化的苯并噻唑与简单烷烃的氧化偶联

Figure 5. Electrophotocatalytic cross-dehydrogenative coupling of benzothiazoles with aliphatic C—H bonds

图6. 光电化学催化杂环C—H键与醛的羟烷基化反应

Figure 6. Electrophotocatalytic hydroxyalkylation of heteroaromatics with aldehydes

图7. 光电化学铈催化的脱羧烷基化反应

Figure 7. Electrophotochemical Ce-catalyzed decarboxylative alkylation of heteroarenes

图8. 光电化学铁催化的脱羧烷基化反应

Figure 8. Electrophotochemical Fe-catalyzed decarboxylative alkylation of heteroarenes

图9. 光电化学铈催化的烷烃C—H键芳基化反应

Figure 9. Electrophotochemical Ce-catalyzed Minisci alkylation of N-heteroarenes with alkanes

图10. 光电化学铈催化的环烷醇的开环官能化反应

Figure 10. Electrophotochemical Ce-catalyzed ring-opening functionalization of cycloalkanols

图11. 光电化学铁催化的烷烃C—H键硼化反应

Figure 11. Electrophotochemical Fe-catalyzed C(sp3)-H borylation of alkanes

图12. 光电化学催化的烷烃C(sp3)—H键叠氮化反应

Figure 12. Electrophotocatalytic azidation of C(sp3)—H bonds

图13. 光电化学双金属铈/锰催化的脂肪酸脱羧叠氮化反应

Figure 13. Ce/Mn dual electrophotocatalytic decarboxylative azidation of aliphatic acids

图14. 光电化学双金属铈/铜催化的不对称脱羧氰基化反应

Figure 14. Ce/Cu dual electrophotocatalytic asymmetric decarboxylative cyanation

图15. 光电化学铜催化的不对称C—H键氰基化反应

Figure 15. Electrophotochemical Cu-catalyzed asymmetric cyanation of benzylic C—H bonds

图16. 光电化学铜催化的芳基烯烃的不对称芳基氰化反应

Figure 16. Electrophotochemical Cu-catalyzed asymmetric heteroarylcyanation of aryl alkenes

图17. 光电化学双金属铈/镍催化的烷基酸脱羧芳基化反应

Figure 17. Ce/Ni dual electrophotocatalytic decarboxylative arylation of aliphatic acids

图18. 光电化学双金属铈/镍催化的脂肪酸脱羧烯基化反应

Figure 18. Ce/Ni dual electrophotocatalytic decarboxylative alkenylation of aliphatic acids

图19. 光电化学双金属铁/镍催化的C(sp3)−H键烯基化反应

Figure 19. Fe/Ni dual electrophotocatalytic C(sp3)−H alkenylation

图20. 光电化学双金属铁/镍催化的烯烃烷基芳基化反应

Figure 20. Fe/Ni dual electrophotocatalytic alkylarylation of alkenes with alkanes

图21. 光电化学双金属铁/镍催化的烯烃烷基酰基化反应

Figure 21. Fe/Ni dual electrophotocatalytic carboacylation of alkenes with alkanes

图22. 光电化学双金属铈/镍催化的醇β-C-C键活化芳基化

Figure 22. Ce/Ni dual electrophotocatalytic deconstructive arylation of alcohols

图23. 光电化学催化的去饱和不对称[2＋2]环化反应

Figure 23. Electrophotocatalytic asymmetric dehydrogenative [2＋2] cycloaddition

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