光电协同催化有机合成研究进展

doi:10.6023/cjoc202105054

摘要/Abstract

随着有机电化学和光化学的复兴, 将两者结合的新型光电协同催化有机化学成为了研究热点之一. 光电协同催化广泛应用于氧化还原及偶联反应等众多反应体系. 本综述总结了近5年来光电催化的最新研究进展, 对反应的机理及催化剂进行了系统性的分类, 总结了该类反应体系的优势和特点, 并且对该研究方向的发展进行了展望.

关键词: 有机电化学, 光化学, 光电化学, 协同催化

Following the renaissances of organic electrochemistry and photochemistry, photoelectrochemical approach was arising as one of hot research areas by combination advantages of photocatalysis and electrocatalysis. The photoeletrocatalysis was widely applied in redox reactions, coupling reactions and beyond. The development of photoelectrochemical transformations during past five years is summarized and the related reactions are classified according to mechanism and catalyst. The current progresses and future outlooks of such method are also discussed.

Key words: organic electrochemistry, photochemistry, photoelectrochemistry, synergistic catalysis

引用此文

杨光, 王衍伟, 仇友爱. 光电协同催化有机合成研究进展[J]. 有机化学, 2021, 41(10): 3935-3947.

Guang Yang, Yanwei Wang, Youai Qiu. Advances in Organic Photoelectrochemical Synergistic Catalysis[J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 3935-3947.

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图/表 20

图1. 早期光电催化反应

Figure 1. Original electrophotocatalyzed transformations

图2. 常见光电催化剂示例

Figure 2. Selected examples of electrophotocatalysts

图3. 三氨基环丙烯离子催化的芳烃与氮杂芳烃氧化偶联反应

Figure 3. Trisaminocyclopropenium catalyzed oxidative coupling of arenes with nitrogen heteroaromatics

图4. TAC催化的醚α位的C—H官能团化反应

Figure 4. TAC catalyzed C—H functionalization of ethers at α-position

图5. 光电催化邻位烷基芳烃双氨化

Figure 5. Electrophotocatalytic diamination of vicinal C—H bonds

图6. 双氰基蒽自由基阳离子催化的芳基卤化物还原偶联反应

Figure 6. Dicyanoanthracene radical cation catalyzed reduction coupling of aryl halides

图7. 光电催化杂芳烃与三氟硼酸酯的C—H烷基化反应

Figure 7. Electrophotocatalyzed C—H alkylation of heteroarenes with organotrifluoroborates

图8. 光电催化杂芳烃与脂肪烃C—H交叉偶联反应

Figure 8. Electrophotocatalyzed cross-coupling of heteroarenes with aliphatic C—H bonds

图9. 光电催化C(sp2)—H三氟甲基化反应

Figure 9. Electrophotocatalyzed trifluoromethylations of C(sp2)—H bond

图10. 光电催化芳烃与唑类的交叉偶联反应

Figure 10. Electrophotocatalyzed cross-coupling of arenes and azoles

图11. 光电催化芳基氟化物的SNAr反应

Figure 11. Electrophotocatalyzed SNAr reactions of aryl fluorides

图12. 电化学调控的黄素催化光化学醇氧化

Figure 12. Electromediated flavin catalyzed photochemical oxidation of alcohols

图13. 光电催化的分子内C(sp3)—H键HLF反应

Figure 13. Electrophotocatalyzed intramolecular C(sp3)—H HLF reaction

图14. 光电参与的锰催化C(sp3)—H氧化叠氮化

Figure 14. Electrophoto- and Mn-catalyzed C(sp3)—H oxidative azidation

图15. 光电催化杂环芳烃与草酸烷基酯的C—H烷基化反应

Figure 15. Electrophotocatalyzed C—H alkylation of heteroarenes with alkyl oxalates

图16. BiVO4光电阳极上的C(sp3)—H键氧化反应

Figure 16. Oxidation of C(sp3)—H bond on BiVO4 photoanode

图17. WO3/BiVO4光电阳极上的呋喃氧化二甲氧基化

Figure 17. Oxidative dimethoxylation of furans on WO3/BiVO4 photoanode

图18. 赤铁矿光电阳极上的芳烃C—H键的胺化反应

Figure 18. C—H bond amination of arenes on hematite photoanode

图19. 流动光电催化芳烃三氟甲基化反应

Figure 19. Continuous-flow electrophotochemical trifluoromethylations of arenes

图20. 流动光电化学C—H烷基化合成吖啶光催化剂

Figure 20. Continuous-flow electrophotochemical C—H alkylation for the synthesis of acridinium photocatalysts

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