氧化型光电催化促进的C—H键官能团化反应研究进展

doi:10.6023/cjoc202311032

摘要/Abstract

惰性C—H键直接选择性官能团化反应是有机合成领域长久以来的挑战之一. 虽然已经发展了多种策略, 但仍亟待发展无需添加过渡金属和氧化剂的新方法. 近年来, 光电催化作为一种新兴策略, 能够在温和条件下实现包括直接C—H键官能团化在内的多种挑战性转化反应, 表现出强大的潜力. 从机理的角度出发, 总结了通过阳极氧化的光电催化策略实现C—H键官能团化反应的最新研究进展, 并简单讨论了这个新兴领域所面临的挑战和机遇.

关键词: 光电催化, 电化学, C—H键官能团化, 氧化反应

Direct and selective functionalization of relatively inert C—H bonds is a long-standing challenge in synthetic chemistry. While many strategies have been developed to date, new approach that does not require the use of transition-metals and oxidants is in high demand. Recently, electrophotocatalysis has emerged as a powerful means to effect direct C—H functionalization and other types of challenging transformations under mild reaction conditions. The recent advances on electrophotocatalytic C—H functionalization via anode oxidation are highlighted with a focus on mechanistic aspects. Challenges and opportunities of this emerging field are also discussed.

Key words: electrophotocatalysis, electrochemistry, C—H functionalization, oxidation

引用此文

Hasil Aman, 常瑞, 叶俊涛. 氧化型光电催化促进的C—H键官能团化反应研究进展[J]. 有机化学, 2024, 44(3): 728-747.

Aman Hasil, Rui Chang, Juntao Ye. Recent Advances on C—H Functionalization via Oxidative Electrophotocatalysis[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 728-747.

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图/表 26

Figure 1. (a) Bond dissociation energies of different C—H bonds,[11] (b) comparisons between photocatalysis, electrocatalysis and electrophotocatalysis (EPC) using oxidation of a substrate (Sub) as an example, and (c) an overview of research on oxidative electrophotocatalytic C—H functionalization since 2019

Scheme 1. Electrophotocatalytic C—H alkylation of heteroarenes with an organotrifluoroborates

Scheme 2. Direct decarboxylative C—H functionalization of heteroarenes and proposed mechanism

Scheme 3. Electrophotochemical undirected C—H trifluoromethylation of unactivated arenes and heteroarenes

Scheme 4. Electrophotochemical trifluoromethylation of arenes using trifluoroacetic acid

Scheme 5. Electrophotocatalytic C—H silylation of heteroarenes through dehydrogenation cross-coupling

Scheme 6. Chloride-promoted electrophotochemical C—H silylation of heteroarenes

Scheme 7. Electrophotocatalytic enantioselective heteroarylcyanation of styrenes

Scheme 8. Electrophotocatalytic methods for the dehydrogenative cross-coupling of arenes with azoles

Scheme 9. Electrophotochemical C—H azolation of arenes using acridinium salt as photooxidants

Scheme 10. C—H amination reaction of arenes with carbamates by using DDQ as a photocatalyst

Scheme 11. Electrophotocatalytic diamination of vicinal C—H bonds

Scheme 12. Electrophotocatalytic Ritter-type amination of benzylic C—H bonds

Scheme 13. Electrophotocatalytic oxygenation of multiple adjacent C—H bonds

Scheme 14. Electrophotocatalytic enantioselective cyanation of benzylic C(sp3)—H bonds

Scheme 15. Electrophotochemical benzylic C(sp3)—H arylation or oxygenative arylation.

Scheme 16. Electrophotochemical manganese-catalyzed oxidative azidation of C(sp3)—H bonds

Scheme 17. Combined electrochemical/photochemical iodide-mediated process for C—H amination

Scheme 18. Accelerated electrophotocatalytic C(sp3)—H heteroarylation enabled by an efficient continuous-flow reactor

Scheme 19. Electrophotocatalytic oxidation of unactivated alcohols via flavin/thiourea co-catalysis

Scheme 20. Regioselective electrophotocatalytic C—H functionalization of ethers

Scheme 21. Electrophotochemical oxidative C(sp3)—H borylation of unactivated hydrocarbons

Scheme 22. Electrophotochemical synthesis of alkylated benzimidazo-fused isoquinolinones

Scheme 23. Electrophotocatalytic cross-coupling of heteroarenes and C(sp3)—H donors

Scheme 24. Dehydrogenative coupling of benzothiazole with strong C(sp3)—H bonds

Scheme 25. Electrophotochemical asymmetric dehydrogenative [2?＋?2] cycloaddition between C—C single and double bonds

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