Recent Advance in Electrochemical C(sp2)—H Amination of Arenes

doi:10.6023/cjoc202310033

Abstract

Aniline and its derivatives are widely used and consumed in human life and industrial production, which inspires the direct aromatic C(sp²)—N construction from the corresponding C(sp²)—H bond. In recent years, as a controllable, sustainable, ambient, and highly scalable methodology, organic electrochemistry has received greater attention and also combined aromatic C(sp²)—N amination, presenting novel reactions. In this review, the common mechanism manifolds of electrochemical aromatic C(sp²)—H amination reactions are summarized, and the reactions examples are classified according to the type of amine sources. The prospects and challenges in this field are provided.

Key words: electrochemistry, amination, arene, aniline, C—H amination

Cite this article

Zile Zhu, Pengfei Li, Youai Qiu. Recent Advance in Electrochemical C(sp²)—H Amination of Arenes[J]. Chinese Journal of Organic Chemistry, 2024, 44(3): 871-891.

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Fig. & Tab. 28

Figure 1. Some molecules containing aromatic C(sp2)—N bond

Scheme 1. (a) Conventional nitration-hydrogenation methods and (b) transition-metal catalyzed methods to construct the aromatic C(sp2)—N bond

Scheme 2. (a) Contemporary routes to implement the amination of aromatic C(sp2)—H, and (b) the advantages of electrochemical methods

Scheme 3. (a) Schematic diagram of direct and indirect electrolysis; (b)~(f) common mechanism manifolds in electrochemical aromatic C(sp2)—H animation

Figure 2. Common amine sources applied in electrochemical aromatic C(sp2)—H amination

Scheme 4. Electrochemical amination reactions with aliphatic secondary amines as the amine sources

Scheme 5. Cobalt-catalyzed electrochemical amination reactions with aliphatic secondary amines as the amine sources

Scheme 6. Copper-catalyzed electrochemical amination reactions with aliphatic secondary amines as the amine sources

Scheme 7. Electrochemical amination reactions with aromatic secondary amines as the amine sources

Scheme 8. Electrochemical amination reactions with aromatic secondary amines as the amine sources

Scheme 9. (a) ACR mechanism with pyridine and nitrile as the amine sources, and (b) electrochemical pyridination and amination reaction

Scheme 10. Electrochemical pyridination and amination reactions

Scheme 11. An electrochemical amination reaction with nitriles as the amine sources

Scheme 12. Electrochemical amination reactions with nitriles as the amine sources

Scheme 13. Electrochemical imidazolation reactions

Scheme 14. Electrochemical pyrazolation reactions

Scheme 15. An electrochemical amination reaction with amides as the amine sources

Scheme 16. Electrochemical amination reactions with amides as the amine sources

Scheme 17. An electrochemical intermolecular annulation reaction

Scheme 18. Electrochemical intramolecular amination reactions constructing (a) benzoxazole and (b) condensed pyridine ring

Scheme 19. Electrochemical intramolecular amination reactions constructing condensed pyridine ring

Scheme 20. An electrochemical intramolecular amination reaction constructing the lactam

Scheme 21. Electrochemical intramolecular amination reactions constructing carbazoles

Scheme 22. Electrochemical intramolecular amination reactions constructing condensed pyrazole and imidazole rings

Scheme 23. (a) Photoelectrochemical reaction where excited photocatalyst oxidizes the substrate and anodic oxidation regenerates the photocatalyst; (b) With the use of photoanode, light excites the VB electrons generating holes (h＋) to oxidize substrates, and the electricity enhances the separation of excited electrons and photo-generated holes

Scheme 24. Photoelectrochemical aromatic amination reactions

Scheme 25. Photoelectrochemical aromatic amination reactions

Scheme 26. Photoelectrochemical aromatic amination reactions applying a photoanode

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电化学芳烃C(sp²)—H胺化反应的研究进展

Recent Advance in Electrochemical C(sp²)—H Amination of Arenes

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电化学芳烃C(sp2)—H胺化反应的研究进展