Recent Advances in Organic Electrophotocatalytic Synthesis

doi:10.6023/cjoc202310034

Abstract

Organic electrophotocatalysis synthesis is recognized as a powerful and scalable methodology for organic synthesis combining photocatalysis and electrolysis synthesis. However, the research in organic electrophotocatalytic synthesis is still in an early stage. In recent years, with the emergence of this strategy, an increasing number of reports have demonstrated the viability and potential of this new methodology to achieve unprecedented transformations. By harnessing light energy and electric energy as driving forces for the reaction, without relying on stoichiometric oxidants or reductants, it enables effective and highly selective redox reactions under relatively mild conditions. Consequently, it finds wide applications in various reaction systems including redox and cross coupling reactions. A comprehensive overview of the latest advancements in organic electrophotocatalysis synthesis in recent years while categorizing the reactions based on their bonding types is provided. The reaction mechanism, advantages and characteristics are also introduced. Finally, the future development direction of organic electrophotocatalytic synthesis is prospected.

Key words: organic electrophotocatalysis, electrochemical synthesis, photochemical synthesis, synergistic catalysis

Cite this article

Zenghui Ye, Huaqing Liu, Fengzhi Zhang. Recent Advances in Organic Electrophotocatalytic Synthesis[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 840-870.

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Fig. & Tab. 41

Figure 1. Trends of organic electrophotocatalytic synthesis publication by years

Scheme 1. Original electrophotocatalytic transformations reported by Moutet and Reverdy

Scheme 2. Electrophotocatalytic vitamin B12-catalyzed conjugate addition of acyl radicals

Scheme 3. Electrophotocatalytic Minisci alkylation of heteroaromatics

Scheme 4. Electrophotocatalytic trifluoromethylation of aromatics

Scheme 5. Electrophotocatalytic Minisci reaction of ether

Scheme 6. Electrophotocatalytic C(sp3)—H arylation

Scheme 7. Electrophotocatalytic decarboxylative Minisci reaction

Scheme 8. Electrophotocatalytic alkylation of benzothiazoles

Scheme 9. Electrophotocatalytic defluorinative arylation of polyfluoroarenes

Scheme 10. Electrophotocatalytic deaminoalkylation Minisci reaction

Scheme 11. Electrophotocatalytic ring-opening functionalization of cyclic alcohols

Scheme 12. Electrophotocatalytic synthesis of nitrogen containing fused compounds

Scheme 13. Electrophotocatalytic decarboxylative coupling of aliphatic carboxylic acids with aryl bromides

Scheme 14. Electrophotocatalytic enantioselective decarboxylative cyanidation

Scheme 15. Electrophotocatalytic enantioselective cyanidation and heteroarylation of olefins

Scheme 16. Electrophotocatalytic enantioselective cyanidation of benzyl C(sp3)—H bond

Scheme 17. Photoelectrochemical Ce-catalyzed for the synthesis of alkylbenzimidazole fused rings

Scheme 18. Electrophotocatalytic TAC-mediated aromatic-azole C—H/N—H coupling reaction

Scheme 19. Electrophotocatalytic TPA-mediated olefin-azole C—H/N—H coupling reaction

Scheme 20. Electrophotocatalytic SNAr reaction of unactivated aryl fluorides

Scheme 21. Electrophotocatalytic HLF reaction

Scheme 22. Electrophotocatalytic azidation of C(sp3)—H bonds

Scheme 23. Electrophotocatalytic aromatic functionalization reaction

Scheme 24. Electrophotocatalytic Ritter-type C—H amination reaction.

Scheme 25. Electrophotocatalytic diamination of vicinal C—H bonds

Scheme 26. Electrophotocatalytic aminooxygenation of aryl olefins

Scheme 27. Electrophotocatalytic decarboxylative azidation of aliphatic carboxylic acids

Scheme 28. Electrophotocatalytic C—H amination of aromatics

Scheme 29. Electrophotocatalytic alcohol oxidation with riboflavin/thioureas

Scheme 30. Electrophotocatalytic acetoxyhydroxylation of aromatics

Scheme 31. Electrophotocatalytic oxidation of multiple adjacent C—H bonds

Scheme 32. Electrophotocatalytic hydroxylation of heteroaromatics with aldehyde

Scheme 33. Electrophotocatalytic epoxidation of olefins

Scheme 34. Electrophotocatalytic epoxidation of olefins

Scheme 35. Electrophotocatalytic reductive functionalization of aryl halide

Scheme 36. Electrophotocatalytic NpMI-catalyzed reductive functionalization of aryl halides

Scheme 37. Photoelectrochemical PDI-catalyzed reductive functionalization of aryl halides

Scheme 38. Electrophotocatalytic 4DPAIPN-catalyzed reductive functionalization of aryl ammonium salt and aryl phosphonates

Scheme 39. Electrophotocatalytic reduction of alkyl phosphates

Scheme 40. Electrophotocatalytic C(sp3)—H boronation

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