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

References 142

[1]	Amini B.; Lowenkron S. In Kirk-Othmer Encyclopedia of Chemical Technology, Ed.: Kirk-Othmer, Wiley, New York, 2003.
[2]	Rappoport Z. The Chemistry of Anilines, 1st ed., Wiley, Chichester, 2007.
[3]	Kahl T.; Schröder K.-W.; Lawrence F. R.; Marshall W. J.; Höke H.; Jäckh R.In Ullmann's Encyclopedia of Industrial Chemistry, Eds.: Elvers, B.; Bellussi, G., Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany, 2011, p. 465-477.
[4]	Anjalin M.; Kanagathara N.; Suganthi A. R. B. Mater. Today Proc. 2020, 33, 4751.
[5]	Shuja M. H.; Shuja S. H.; Shakil F.; Ahmed I. Ann. Med. Surg. 2023, 85, 1346. doi: 10.1097/MS9.0000000000000303
[6]	Niu W.; Li L.; Liu X.; Wang N.; Liu J.; Zhou W.; Tang Z.; Chen S. J. Am. Chem. Soc. 2015, 137, 5555. doi: 10.1021/jacs.5b02027
[7]	Vervoort J.; De Jager P. A.; Steenbergen J.; Rietjens I. M. C. M. Xenobiotica 1990, 20, 657. pmid: 2238701
[8]	Duckett C. J.; Lindon J. C.; Walker H.; Abou-Shakra F.; Wilson I. D; Nicholson J. K. Xenobiotica 2006, 36, 59. pmid: 16507513
[9]	MacKetta J. J. In Encyclopedia of Chemical Processing and Design, Dekker, New York, 1990.
[10]	Béchamp Reduction, In Comprehensive Organic Name Reactions and Reagents, Wiley, Hoboken, NJ, 2010, pp. 284-287.
[11]	Porter H. K. In Organic Reactions, Ed.: Denmark, S. E., Wiley, 2011, pp. 455-481, doi: 10.1002/0471264180.or074.03.
[12]	Driessen R. T.; Kamphuis P.; Mathijssen L.; Zhang R.; Van Der Ham, L. G. J.; Van Den Berg, H.; Zeeuw, A. J. Chem. Eng. Technol. 2017, 40, 838. doi: 10.1002/ceat.v40.5
[13]	Moreno S. N.; Docampo R. Environ. Health Perspect. 1985, 64, 199. doi: 10.1289/ehp.8564199
[14]	Goldberg I. Ber. Dtsch. Chem. Ges. 1906, 39, 1691. doi: 10.1002/cber.v39:2
[15]	Allen C. F. H.; McKee G. H. W. Org. Synth. 1939, 19, 6. doi: 10.15227/orgsyn.019.0006
[16]	Paul F.; Patt J.; Hartwig J. F. J. Am. Chem. Soc. 1994, 116, 5969. doi: 10.1021/ja00092a058
[17]	Guram A. S.; Buchwald S. L. J. Am. Chem. Soc. 1994, 116, 7901. doi: 10.1021/ja00096a059
[18]	Chan D. M. T.; Monaco K. L.; Wang R.-P.; Winters M. P. Tetrahedron Lett. 1998, 39, 2933. doi: 10.1016/S0040-4039(98)00503-6
[19]	Lam P. Y. S.; Clark C. G.; Saubern S.; Adams J.; Winters M. P.; Chan D. M. T.; Combs A. Tetrahedron Lett. 1998, 39, 2941.
[20]	Burns N. Z.; Baran P. S.; Hoffmann R. W. Angew. Chem., Int. Ed. 2009, 48, 2854. doi: 10.1002/anie.v48:16
[21]	Louillat M.-L.; Patureau F. W. Chem. Soc. Rev. 2014, 43, 901. doi: 10.1039/C3CS60318K
[22]	Park Y.; Kim Y.; Chang S. Chem. Rev. 2017, 117, 9247. doi: 10.1021/acs.chemrev.6b00644
[23]	Yang Y.; Zhang D.; Vessally E. Top. Curr. Chem. 2020, 378, 37.
[24]	Beletskaya I. P.; Averin A. D. Russ. Chem. Rev. 2021, 90, 1359. doi: 10.1070/RCR4999
[25]	Feng Y.-L.; Shi B.-F. Chin. J. Org. Chem. 2021, 41, 3753. (in Chinese) doi: 10.6023/cjoc202104004
	( 冯亚岚, 史炳锋, 有机化学, 2021, 41, 3753.) doi: 10.6023/cjoc202104004
[26]	Ravindar L.; Hasbullah S. A.; Hassan N. I.; Qin H. Eur. J. Org. Chem. 2022, 31, e202200596.
[27]	Krishna Rao M. V.; Kareem S.; Vali S. R.; Subba Reddy B. V. Org. Biomol. Chem. 2023, 21, 8426. doi: 10.1039/D3OB01160G
[28]	Boursalian G. B.; Ngai M. Y.; Hojczyk K. N.; Ritter T. J. Am. Chem. Soc. 2013, 135, 13278. doi: 10.1021/ja4064926 pmid: 23998528
[29]	Roy S.; Panja S.; Sahoo S. R.; Chatterjee S.; Maiti D. Chem. Soc. Rev. 2023, 52, 2391. doi: 10.1039/D0CS01466D
[30]	Muñiz K. Acc. Chem. Res. 2018, 51, 1507. doi: 10.1021/acs.accounts.8b00137
[31]	Kärkäs M. D. Chem. Soc. Rev. 2018, 47, 5786. doi: 10.1039/C7CS00619E
[32]	Liu C.; Liu J.; Li W.; Lu H.; Zhang Y. Org. Chem. Front. 2023, 10, 5309. doi: 10.1039/D3QO01159C
[33]	Zhang H.; Lei A. Synthesis 2019, 51, 83. doi: 10.1055/s-0037-1610380
[34]	Meng Z.; Feng C.; Xu K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese) doi: 10.6023/cjoc202012013
	( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.) doi: 10.6023/cjoc202012013
[35]	Chen N.; Xu H. Green Synth. Catal. 2021, 2, 165.
[36]	Wang H.; Gao X.; Lv Z.; Abdelilah T.; Lei A. Chem. Rev. 2019, 119, 6769. doi: 10.1021/acs.chemrev.9b00045
[37]	Lu L.; Shi R.; Lei A. Trends Chem. 2022, 4, 179. doi: 10.1016/j.trechm.2021.12.008
[38]	Cavedon C.; Seeberger P. H.; Pieber B. Eur. J. Org. Chem. 2020, 2020, 1379. doi: 10.1002/ejoc.v2020.10
[39]	Singh S.; Roy V. J.; Dagar N.; Sen P. P.; Roy S. R. Adv. Synth. Catal. 2021, 363, 937. doi: 10.1002/adsc.v363.4
[40]	Kwon K.; Simons R. T.; Nandakumar M.; Roizen J. L. Chem. Rev. 2022, 122, 2353. doi: 10.1021/acs.chemrev.1c00444
[41]	Holmberg-Douglas N.; Nicewicz D. A. Chem. Rev. 2022, 122, 1925. doi: 10.1021/acs.chemrev.1c00311
[42]	Chan C.; Chow Y.; Yu W. Synthesis 2020, 52, 2899.
[43]	Frontana-Uribe B. A.; Little R. D.; Ibanez J. G.; Palma A.; Vasquez-Medrano R. Green Chem. 2010, 12, 2099. doi: 10.1039/c0gc00382d
[44]	Luca O. R.; Gustafson J. L.; Maddox S. M.; Fenwick A. Q.; Smith D. C. Org. Chem. Front. 2015, 2, 823. doi: 10.1039/C5QO00075K
[45]	Yan M.; Kawamata Y.; Baran P. S. Chem. Rev. 2017, 117, 13230. doi: 10.1021/acs.chemrev.7b00397
[46]	Wiebe A.; Gieshoff T.; Möhle S.; Rodrigo E.; Zirbes M.; Waldvogel S. R. Angew. Chem., Int. Ed. 2018, 57, 5594. doi: 10.1002/anie.v57.20
[47]	Shida N.; Zhou Y.; Inagi S. Acc. Chem. Res. 2019, 52, 2598. doi: 10.1021/acs.accounts.9b00337
[48]	Kingston C.; Palkowitz M. D.; Takahira Y.; Vantourout J. C.; Peters B. K.; Kawamata Y.; Baran P. S. Acc. Chem. Res. 2020, 53, 72. doi: 10.1021/acs.accounts.9b00539
[49]	Novaes L. F. T.; Liu J.; Shen Y.; Lu L.; Meinhardt J. M.; Lin S. Chem. Soc. Rev. 2021, 50, 7941. doi: 10.1039/d1cs00223f pmid: 34060564
[50]	Feng T.; Wang S.; Qiu Y. Synlett 2022, 33, 1582. doi: 10.1055/a-1828-1217
[51]	Ogibin Y. N.; Elinson M. N.; Nikishin G. I. Russ. Chem. Rev. 2009, 78, 89. doi: 10.1070/RC2009v078n02ABEH003886
[52]	Francke R.; Little R. D. Chem. Soc. Rev. 2014, 43, 2492. doi: 10.1039/c3cs60464k pmid: 24500279
[53]	Tay N. E. S.; Lehnherr D.; Rovis T. Chem. Rev. 2022, 122, 2487. doi: 10.1021/acs.chemrev.1c00384
[54]	Mruthunjaya A. K. V.; Torriero A. A. J. Molecules 2023, 28, 471. doi: 10.3390/molecules28020471
[55]	Roth H.; Romero N.; Nicewicz D. Synlett 2015, 27, 714. doi: 10.1055/s-00000083
[56]	Wawzonek S.; McIntyre T. W. J. Electrochem. Soc. 1967, 114, 1025. doi: 10.1149/1.2424177
[57]	Dvořák V.; Němec I.; Zýka J. Microchem. J. 1967, 12, 99. doi: 10.1016/0026-265X(67)90012-4
[58]	Paduszek B.; Kalinowski M. K. Electrochim. Acta 1983, 28, 639. doi: 10.1016/0013-4686(83)85057-9
[59]	Loveland J. W.; Dimeler G. R. Anal. Chem. 1961, 33, 1196. doi: 10.1021/ac60177a022
[60]	O’Donnell, J. F.; Mann, C. K. J. Electroanal. Chem. Interfacial Electrochem. 1967, 13, 157. doi: 10.1016/0022-0728(67)80108-6
[61]	Merkel P. B.; Luo P.; Dinnocenzo J. P.; Farid S. J. Org. Chem. 2009, 74, 5163. doi: 10.1021/jo9011267 pmid: 19588891
[62]	Kita Y.; Tohma H.; Hatanaka K.; Takada T.; Fujita S.; Mitoh S.; Sakurai H.; Oka S. J. Am. Chem. Soc. 1994, 116, 3684. doi: 10.1021/ja00088a003
[63]	Ischay M. A.; Yoon T. P. Eur. J. Org. Chem. 2012, 2012, 3359. doi: 10.1002/ejoc.v2012.18
[64]	Yi H.; Zhang G.; Wang H.; Huang Z.; Wang J.; Singh A. K.; Lei A. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
[65]	Cui H.-L. Org. Biomol. Chem. 2020, 18, 2975. doi: 10.1039/D0OB00441C
[66]	Pistritto V. A.; Liu S.; Nicewicz D. A. J. Am. Chem. Soc. 2022, 144, 15118. doi: 10.1021/jacs.2c04577 pmid: 35944280
[67]	Michejda C. J. W.; Hoss P. J. Am. Chem. Soc. 1970, 92, 6298. doi: 10.1021/ja00724a032
[68]	Danen W. C.; Neugebauer F. A. Angew. Chem. Int. Ed. Engl. 1975, 14, 783. doi: 10.1002/anie.v14:12
[69]	Chow Y. L.; Danen W. C.; Nelsen S. F.; Rosenblatt D. H. Chem. Rev. 1978, 78, 243. doi: 10.1021/cr60313a003
[70]	Zard S. Z. Chem. Soc. Rev. 2008, 37, 1603. doi: 10.1039/b613443m
[71]	Xiong T.; Zhang Q. Chem. Soc. Rev. 2016, 45, 3069. doi: 10.1039/c5cs00852b pmid: 27116936
[72]	Boursalian G. B.; Ham W. S.; Mazzotti A. R.; Ritter T. Nat. Chem. 2016, 8, 810. doi: 10.1038/nchem.2529 pmid: 27442288
[73]	Pratley C.; Fenner S.; Murphy J. A. Chem. Rev. 2022, 122, 8181. doi: 10.1021/acs.chemrev.1c00831 pmid: 35285636
[74]	Gao W.; Li W.; Zeng C.; Tian H.; Hu L.; Little R. J. Org. Chem. 2014, 79, 9613. doi: 10.1021/jo501736w
[75]	Qiu Y.; Struwe J.; Meyer T. H.; Oliveira J. C. A.; Ackermann L. Chem.-Eur. J. 2018, 24, 12784. doi: 10.1002/chem.v24.49
[76]	Gao X.; Wang P.; Zeng L.; Tang S.; Lei A. J. Am. Chem. Soc. 2018, 140, 4195. doi: 10.1021/jacs.7b13049
[77]	Sauermann N.; Mei R.; Ackermann L. Angew. Chem., Int. Ed. 2018, 57, 5090. doi: 10.1002/anie.v57.18
[78]	Zhang S.; Samanta R. C.; Sauermann N.; Ackermann L. Chem.- Eur. J. 2018, 24, 19166. doi: 10.1002/chem.v24.72
[79]	Kathiravan S.; Suriyanarayanan S.; Nicholls I. A. Org. Lett. 2019, 21, 1968. doi: 10.1021/acs.orglett.9b00003 pmid: 30785289
[80]	Yang Q.; Wang X.; Lu J.; Zhang L.; Fang P.; Mei T. J. Am. Chem. Soc. 2018, 140, 11487. doi: 10.1021/jacs.8b07380
[81]	Tang S.; Wang S.; Liu Y.; Cong H.; Lei A. Angew. Chem. Int. Ed. 2018, 57, 4737. doi: 10.1002/anie.v57.17
[82]	Liu K.; Tang S.; Wu T.; Wang S.; Zou M.; Cong H.; Lei A. Nat. Commun. 2019, 10, 639. doi: 10.1038/s41467-019-08414-8
[83]	Wu Y.; Jiang S.; Song R.; Li J. Chem. Commun. 2019, 55, 4371. doi: 10.1039/C9CC01332F
[84]	Chen S.; Li Y.; Xiang S.; Li S.; Tan B. Chem. Commun. 2021, 57, 8512. doi: 10.1039/D1CC03276C
[85]	Feng C.; Liu X.; She Y.; Shen Z.; Li M. Chin. Chem. Lett. 2023, 34, 107935. doi: 10.1016/j.cclet.2022.107935
[86]	Wang Z.; Cheng Q.; Peng R.; Yan P.; Zeng R.; Tian W.; Pan B.; Gu J.; Li Y.; Ouyang Q. J. Org. Chem. 2022, 87, 4742. doi: 10.1021/acs.joc.2c00031
[87]	Zincke Th.; Heuser G.; Möller W. Justus Liebigs Ann. Chem. 1904, 333, 296. doi: 10.1002/jlac.v333:2/3
[88]	Ritter J. J.; Kalish J. J. Am. Chem. Soc. 1948, 70, 4048. doi: 10.1021/ja01192a023
[89]	Lund H.; Tegnér C.; Takman B. Acta Chem. Scand. 1957, 11, 1323. doi: 10.3891/acta.chem.scand.11-1323
[90]	Shine H. J.; Silber J. J.; Bussey R. J.; Okuyama T. J. Org. Chem. 1972, 37, 2691. doi: 10.1021/jo00982a014
[91]	Blackburn G. M.; Will J. P. J. Chem. Soc., Chem. Commun. 1974, 67.
[92]	Ruhlmann L.; Schulz A.; Giraudeau A.; Messerschmidt C.; Fuhrhop J. H. J. Am. Chem. Soc. 1999, 121, 6664. doi: 10.1021/ja984404r
[93]	Li Y.; Kamata K.; Kawai T.; Abe J.; Iyoda T. J. Chem. Soc., Perkin 1 2002, 1135.
[94]	Li Y.; Asaoka S.; Yamagishi T.; Iyoda T. Electrochemistry 2004, 72, 171. doi: 10.5796/electrochemistry.72.171
[95]	Morofuji T.; Shimizu A.; Yoshida J. Angew. Chem., Int. Ed. 2012, 51, 7259. doi: 10.1002/anie.v51.29
[96]	Morofuji T.; Shimizu A.; Yoshida J. J. Am. Chem. Soc. 2013, 135, 5000. doi: 10.1021/ja402083e pmid: 23510504
[97]	Herold S.; Möhle S.; Zirbes M.; Richter F.; Nefzger H.; Waldvogel S. R. Eur. J. Org. Chem. 2016, 2016, 1274.
[98]	Möhle S.; Herold S.; Richter F.; Nefzger H.; Waldvogel S. R. ChemElectroChem 2017, 4, 2196. doi: 10.1002/celc.v4.9
[99]	Wesenberg L. J.; Herold S.; Shimizu A.; Yoshida J.; Waldvogel S. R. Chem.-Eur. J. 2017, 23, 12096. doi: 10.1002/chem.201701979 pmid: 28605084
[100]	Strekalova S.; Kononov A.; Rizvanov I.; Budnikova Y. RSC Adv. 2021, 11, 37540. doi: 10.1039/d1ra07650g pmid: 35496383
[101]	Taily I. M.; Saha D.; Banerjee P. Org. Lett. 2022, 24, 2310. doi: 10.1021/acs.orglett.2c00439
[102]	Fu Y.; Zhang L.; Sun M.; Cao L.; Yang L.; Cheng R.; Ma Y.; Ye J. Eur. J. Org. Chem. 2023, 26, e202300553. doi: 10.1002/ejoc.v26.35
[103]	Morofuji T.; Shimizu A.; Yoshida J. J. Am. Chem. Soc. 2014, 136, 4496. doi: 10.1021/ja501093m pmid: 24625055
[104]	Morofuji T.; Shimizu A.; Yoshida J. J. Am. Chem. Soc. 2015, 137, 9816. doi: 10.1021/jacs.5b06526 pmid: 26225441
[105]	De Robillard G.; Makni O.; Cattey H.; Andrieu J.; Devillers C. H. Green Chem. 2015, 17, 4669. doi: 10.1039/C5GC01142F
[106]	Yu Y.; Yuan Y.; Liu H.; He M.; Yang M.; Liu P.; Yu B.; Dong X.; Lei A. Chem. Commun. 2019, 55, 1809. doi: 10.1039/C8CC09899A
[107]	Wang J.-H.; Lei T.; Nan X.-L.; Wu H.-L.; Li X.-B.; Chen B.; Tung C.-H.; Wu L.-Z. Org. Lett. 2019, 21, 5581. doi: 10.1021/acs.orglett.9b01910
[108]	Sun M.; Zhou Y.; Li L.; Wang L.; Ma Y.; Li P. Org. Chem. Front. 2021, 8, 754. doi: 10.1039/D0QO01088J
[109]	Buglioni L.; Beslać M.; Noël T. J. Org. Chem. 2021, 86, 16195. doi: 10.1021/acs.joc.1c01409
[110]	Zhou N.; Zhao J.; Sun C.; Lai Y.; Ruan Z.; Feng P. J. Org. Chem. 2021, 86, 16059. doi: 10.1021/acs.joc.1c01271
[111]	Xu H.-C.; Campbell J. M.; Moeller K. D. J. Org. Chem. 2014, 79, 379. doi: 10.1021/jo402623r
[112]	Hu X.; Zhang G.; Nie L.; Kong T.; Lei A. Nat. Commun. 2019, 10, 5467. doi: 10.1038/s41467-019-13524-4
[113]	Zhang Y.; Lin Z.; Ackermann L. Chem.-Eur. J. 2021, 27, 242. doi: 10.1002/chem.202004229 pmid: 33085807
[114]	Peng X.; Zhao J.; Ma G.; Wu Y.; Hu S.; Ruan Z.; Feng P. Green Chem. 2021, 23, 8853. doi: 10.1039/D1GC02821A
[115]	Puthanveedu M.; Khamraev V.; Brieger L.: Strohmann C.; Antonchick A. P. Chem.-Eur. J. 2021, 27, 8008. doi: 10.1002/chem.202100960 pmid: 33931904
[116]	Zhang Y.-Z.; Mo Z.-Y.; Wang H.-S.; Wen X.-A.; Tang H.-T.; Pan Y.-M. Green Chem. 2019, 21, 3807. doi: 10.1039/C9GC01201J
[117]	Luo M.-J.; Ouyang X.-H.; Zhu Y.-P.; Li Y.; Li J.-H. Green Chem. 2021, 23, 9024. doi: 10.1039/D1GC02922C
[118]	Wang H.; Zheng Y.; Xu H.; Zou J.; Jin C. Front. Chem. 2022, 10, 950635. doi: 10.3389/fchem.2022.950635
[119]	Morofuji T.; Shimizu A.; Yoshida J. Chem.-Eur. J. 2015, 21, 3211. doi: 10.1002/chem.201406398 pmid: 25641711
[120]	Ohno Y.; Ando S.; Furusho D.; Hifumi R.; Nagata Y.; Tomita I.; Inagi S. Org. Lett. 2023, 25, 3951. doi: 10.1021/acs.orglett.3c01341
[121]	Zhao H.; Liu Z.; Song J.; Xu H. Angew. Chem., Int. Ed. 2017, 56, 12732. doi: 10.1002/anie.v56.41
[122]	Zhao H.; Xu P.; Song J.; Xu H. Angew. Chem., Int. Ed. 2018, 57, 15153. doi: 10.1002/anie.v57.46
[123]	Zhang S.; Li L.; Xue M.; Zhang R.; Xu K.; Zeng C. Org. Lett. 2018, 20, 3443. doi: 10.1021/acs.orglett.8b00981
[124]	Zhang P.; Li B.; Niu L.; Wang L.; Zhang G.; Jia X.; Zhang G.; Liu S.; Ma L.; Gao W.; Qin D.; Chen J. Adv. Synth. Catal. 2020, 362, 2342. doi: 10.1002/adsc.v362.12
[125]	Wang Q.; Zhang X.; Wang P.; Gao X.; Zhang H.; Lei A. Chin. J. Chem. 2021, 39, 143. doi: 10.1002/cjoc.v39.1
[126]	Zhang H.; Ye Z.; Chen N.; Chen Z.; Zhang F. Green Chem. 2022, 24, 1463. doi: 10.1039/D1GC04534B
[127]	Wan H.; Li D.; Xia H.; Yang L.; Alhumade H.; Yi H.; Lei A. Chem. Commun. 2022, 58, 665. doi: 10.1039/D1CC04656J
[128]	Zhao H.; Hou Z.; Liu Z.; Zhou Z.; Song J.; Xu H. Angew. Chem., Int. Ed. 2017, 56, 587. doi: 10.1002/anie.v56.2
[129]	Zhao H.; Zhuang J.; Xu H. ChemSusChem 2021, 14, 1692. doi: 10.1002/cssc.v14.7
[130]	Duan Z.; Zhang L.; Zhang W.; Lu L.; Zeng L.; Shi R.; Lei A. ACS Catal. 2020, 10, 3828. doi: 10.1021/acscatal.0c00103
[131]	Yang G.; Wang Y.; Qiu Y. Chin. J. Org. Chem. 2021, 41, 3935. (in Chinese) doi: 10.6023/cjoc202105054
	( 杨光, 王衍伟, 仇友爱, 有机化学, 2021, 41, 3935.) doi: 10.6023/cjoc202105054
[132]	Li P.; Zhang T.; Mushtaq M. A.; Wu S.; Xiang X.; Yan D. Chem. Rec. 2021, 21, 841. doi: 10.1002/tcr.v21.4
[133]	Huang H.; Steiniger K. A.; Lambert T. H. J. Am. Chem. Soc. 2022, 144, 12567. doi: 10.1021/jacs.2c01914 pmid: 35816101
[134]	Qian L.; Shi M. Chem. Commun. 2023, 59, 3487. doi: 10.1039/D3CC00437F
[135]	Decker F.; Cattarin S. In Encyclopedia of Electrochemical Power Sources, Elsevier, Amsterdam, 2009, pp. 1-9.
[136]	Huang H.; Strater Z. M.; Rauch M.; Shee J.; Sisto T. J.; Nuckolls C.; Lambert T. H. Angew. Chem., Int. Ed. 2019, 58, 13318. doi: 10.1002/anie.v58.38
[137]	Hou Z.; Xu H. ChemElectroChem 2021, 8, 1571. doi: 10.1002/celc.v8.9
[138]	Wu S.; Žurauskas J.; Domański M.; Hitzfeld P. S.; Butera V.; Scott D. J.; Rehbein J.; Kumar A.; Thyrhaug E.; Hauer J.; Barham J. P. Org. Chem. Front. 2021, 8, 1132. doi: 10.1039/D0QO01609H
[139]	Huang H.; Lambert T. H. Angew. Chem., Int. Ed. 2021, 60, 11163. doi: 10.1002/anie.v60.20
[140]	Hou Z.-W.; Yan H.; Song J.; Xu H.-C. Green Chem. 2023, 25, 7959. doi: 10.1039/D3GC02126B
[141]	Zhang L.; Liardet L.; Luo J.; Ren D.; Grätzel M.; Hu X. Nat. Catal. 2019, 2, 366. doi: 10.1038/s41929-019-0231-9
[142]	Carey F. A.; Sundberg R. J. Advanced Organic Chemistry, Springer US, Boston, MA, 2007.

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