自由基介导的硝基芳烃活化反应研究进展

doi:10.6023/cjoc202502017

摘要/Abstract

硝基芳烃是化学工业中最廉价和易得的原料之一, 通常被用作多功能构件. 含氮化合物的合成以往主要依赖于苯胺, 然而与苯胺相比, 利用硝基芳烃可以节省一步或多步步骤. 因此, 以硝基芳烃作为潜在的氨源构建含氮化合物成为近年研究热点之一. 由于自由基具有高活性、反应条件温和以及良好的官能团兼容等优点, 近年来自由基介导的硝基芳烃活化已经取得了较好的进展, 实现了多种多样的反应类型. 根据不同反应分类, 综述了近十年在不同催化条件下自由基介导的硝基芳烃活化反应研究进展, 详细讨论了反应底物普适性、机理和应用, 并对该领域的发展前景和局限性进行了总结.

关键词: 硝基芳烃, 自由基, 活化反应, 含氮化合物

Nitroarene is one of the cheapest and most readily available raw materials in the chemical industry and is often used as multifunctional building blocks. In the past, the synthesis of nitrogen-containing compounds mainly depended on aniline. However, the utilization of nitroarenes can save one or more steps as compared to anilines. Therefore, the construction of nitrogen-containing compounds using nitroarenes as potential amino sources has become one of the research hotspots in recent years. Due to the advantages of radicals, such as high activity, mild reaction conditions, and good functional group compatibility, good progress has been made on radical-mediated activation of nitroarenes in recent years, and a variety of reaction types have been implemented. In this review, the recent progress in radical-mediated activation of nitroarenes under different catalytic conditions is summarized. The reaction substrate compatibility, mechanism, applications, advantages, and limitations in this field are also discussed in detail.

Key words: nitroarenes, radical, activation reaction, nitrogen-containing compounds

引用此文

张斌斌, 刘露娜, 竺杨彬, 邹东. 自由基介导的硝基芳烃活化反应研究进展[J]. 有机化学, 2025, 45(8): 2698-2725.

Binbin Zhang, Lu'na Liu, Yangbin Zhu, Dong Zou. Recent Progress on Radical-Mediated Activation of Nitroarenes[J]. Chinese Journal of Organic Chemistry, 2025, 45(8): 2698-2725.

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图/表 39

图式1. 铁催化的烯烃与硝基芳烃氢胺化反应

Scheme 1. Fe-catalyzed hydroamination of olefins with nitro- arenes

图式2. 铁催化的卤化物与硝基芳烃还原偶联反应

Scheme 2. Fe-catalyzed reductive coupling of alkyl halides with nitroarenes

图式3. 铜催化的硝基芳烃与4-烷基-1,4-二氢吡啶的交叉偶联反应

Scheme 3. Cu-catalyzed cross-coupling of nitroarenes with 4- alkyl-1,4-dihydropyridines

图式4. 镍催化卤代芳烃与硝基芳烃的C—N偶联反应

Scheme 4. Ni-catalyzed C—N coupling of aryl halides with nitroarenes

图式5. 硝基芳烃的光诱导还原及其与卤代芳烃的串联C—N交叉偶联

Scheme 5. Photoinduced reduction of nitroarenes and tandem C—N cross-coupling with haloarenes

图式6. 铁催化羧酸与硝基芳烃的脱羧C—N偶联反应

Scheme 6. Fe-catalyzed decarboxylation C—N coupling of carboxylic acid with nitroarenes

图式7. 铁催化的硝基芳烃脱羧胺化合成仲胺

Scheme 7. Fe-catalyzed decarboxylative amination with nitroarenes to construct secondary amines

图式8. 可见光协同镍催化的三组分胺化反应

Scheme 8. Visible light-assisted nickel-catalyzed amination of three components

图式9. 双镍/光催化合成N-甲酰基N,N'-二芳基乙二胺

Scheme 9. Dual nickel/photoredox-catalyzed synthesis of N-formyl N,N'-diaryl ethylenediamines

图式10. 金属光催化的三重偶联反应合成复杂的N-三氟烷基苯胺

Scheme 10. Metallaphotocatalytic triple couplings for modular synthesis of elaborate N-trifluoroalkyl anilines

图式11. 钴催化的硝基芳烃选择性还原反应

Scheme 11. Co-catalyzed chemoselective reduction of nitro- arenes

图式12. 可见光促进的硝基芳烃选择性还原为芳胺

Scheme 12. Selective reduction of nitroarenes to aryl amines promoted by visible light

图式13. 可见光介导的未活化烷烃与硝基芳烃的C—H胺化反应

Scheme 13. Visible-light-mediated C—H amination of unactivated alkanes with nitroarenes

图式14. 未活化烷烃与硝基芳烃的C—H胺化反应机制

Scheme 14. Proposed mechanism of C—H amination of unactivated alkanes with nitroarenes

图式15. 电还原羧酸和硝基芳烃偶联反应

Scheme 15. Electroreductive carboxylic acids and nitroarenes coupling reaction

图式16. 铁催化的硝基芳烃和苯甲醛合成酰胺反应

Scheme 16. Fe-catalyzed synthesis of amides from nitroarenes and benzaldehydes

图式17. 光催化硝基芳烃合成亚磺酰胺和亚砜

Scheme 17. Photocatalytic synthesis of sulfinamides and sulfoxides from nitroarenes

图式18. 无过渡金属催化的硝基芳烃合成硫代酰胺

Scheme 18. Transition metal-free synthesis of thioamides from nitroarenes

图式19. 芳基α-酮羧酸与硝基芳烃的脱羧/氧化酰胺化反应

Scheme 19. Decarboxylative/oxidative amidation of aryl α-ketocarboxylic acids with nitroarenes

图式20. 可见光诱导的邻硝基芳烃分子内还原环化合成喹唑啉酮类衍生物

Scheme 20. Visible-light-induced intramolecular reductive cyclization of o-nitroarenes for the synthesis of quinazolinone derivatives

图式21. 光催化硝基芳烃还原/环化合成喹唑啉酮衍生物

Scheme 21. Photo-driven reduction/cyclization of nitroarenes for the synthesis of quinazolinone derivatives

图式22. 可见光催化的硝基芳烃[1＋2＋2]环加成反应

Scheme 22. Visible-light catalyzed [1＋2＋2] cycloaddition of nitroarenes

图式23. 可见光诱导的哌啶α,γ-C(sp3)—H双官能化反应

Scheme 23. Visible-light-induced α,γ-C(sp3)—H difunctionalization of piperidines

图式24. 光诱导硝基芳烃和胺的氧化还原串联反应

Scheme 24. Photo-induced redox cascade reaction of nitroarenes and amines

图式25. 2-硝基芳基乙醇的可切换氧化还原环化反应

Scheme 25. Switchable redox annulation of 2-nitroarylethanols affording N-heterocycles

图式26. 硝基芳烃脱芳化扩环合成多取代氮杂烷

Scheme 26. Synthesis of polysubstituted azepanes by dearomative ring expansion of nitroarenes

图式27. 由N,N-二烷基-3-硝基苯胺合成2-芳基苯并噻唑-5-胺的方案

Scheme 27. Synthesis of 2-arylbenzothiazol-5-amines from N,N-dialkyl-3-nitroanilines

图式28. 无过渡金属催化的硝基芳烃和醛亚胺环加成反应

Scheme 28. Transition-metal-free cycloadditions of nitroarenes and aldimines

图式29. N-杂环卡宾催化硝基芳烃和肉桂醛的不对称羟基化反应研究

Scheme 29. Enantioselective N-heterocyclic carbene-catalyzed β-hydroxylation of enals using nitroarenes

图式30. NHC催化氧原子不对称转移到肉桂醛的研究

Scheme 30. NHC-catalyzed enantioselective transferring of oxygen atoms to enals

图式31. 铁催化的硝基芳烃和烯烃水合反应

Scheme 31. Fe-catalyzed hydration of alkenes using nitroarenes

图式32. 硝基芳烃分子内自由基氧转移反应

Scheme 32. Intramolecular radical oxygen-transfer reactions using nitroarenes

图式33. 硝基芳烃作为光敏氧化剂的烯烃二羟基化反应

Scheme 33. Olefin dihydroxylation using nitroarenes as photoresponsive oxidants

图式34. 光激发硝基芳烃促进脂肪族体系的厌氧C—H羟基化反应

Scheme 34. Anaerobic C—H hydroxylation of aliphatic systems promoted by photoexcited nitroarenes.

图式35. 硝基芳烃用于烯烃厌氧裂解的光诱导氧转移反应

Scheme 35. Photoinduced oxygen transfer using nitroarenes for the anaerobic cleavage of alkenes

图式36. 光激发硝基芳烃对烯烃的氧化裂解

Scheme 36. Photoexcited nitroarenes for the oxidative cleavage of alkenes

图式37. 无过渡金属催化的硝基氧转移构建N-苯甲酰基苯甲酰胺产物

Scheme 37. Transition-metal-free oxygen transfer using nitroarenes for the synthesis of N-benzoylbenzamidinates

图式38. 铜催化硝基芳烃氧转移直接合成2-氨基苯酚衍生物

Scheme 38. Cu-catalyzed oxygen transfer using nitroarenes for direct synthesis of 2-aminophenol derivatives

图式39. 光诱导下聚合物的羰基化修饰新方法

Scheme 39. A new method of photoinduced carbonylation modification of polymers

参考文献 83

[1]	(a) Martins, P.; Jesus, J.; Santos, S.; Raposo, L. R.; Roma-Ro- drigues, C.; Baptista, P. V.; Fernandes, A. R. Molecules 2015, 20, 16852. doi: 10.3390/molecules200916852 pmid: 29714475
	(b) Abdildinova, A.; Gong, Y.-D. ACS Comb. Sci. 2018, 20, 309. doi: 10.1021/acscombsci.8b00044 pmid: 29714475
[2]	(a) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450. pmid: 27689804
	(b) Wegener, G.; Brandt, M.; Duda, L.; Hofmann, J.; Klesczewski, B.; Koch, D.; Kumpf, R.-J.; Orzesek, H.; Pirkl, H.-G.; Six, C.; Steinlein, C.; Weisbeck, M. Appl. Catal. A 2001, 221, 303. pmid: 27689804
	(c) Ruiz-Castillo, P.; Buchwald, S. L. Chem. Rev. 2016, 116, 12564. pmid: 27689804
	(d) Surry, D. S.; Buchwald, S. L. Angew. Chem., nt. Ed. 2008, 47, 6338. pmid: 27689804
	(e) Surry, D. S.; Buchwald, S. L. Chem. Sci. 2011, 2, 27. pmid: 27689804
[3]	(a) Orlandi, M.; Brenna, D.; Harms, R.; Jost, S.; Benaglia, M. Org. Process Res. Dev. 2018, 22, 430. pmid: 23560824
	(b) Tomkins, P.; Gebauer-Henke, E.; Leitner, W.; Müller, T. E. ACS Catal. 2015, 5, 203. pmid: 23560824
	(c) Cantillo, D.; Moghaddam, M. M.; Kappe, C. O. J. Org. Chem. 2013, 78, 4530. doi: 10.1021/jo400556g pmid: 23560824
[4]	Gui, J.; Pan, C.-M.; Jin, Y.; Qin, T.; Lo, J. C.; Lee, B. J.; Spergel, S. H.; Mertzman, M. E.; Pitts, W. J.; La Cruz, T. E.; Schmidt, M. A.; Darvatkar, N.; Natarajan, S. R.; Baran, P. S. Science 2015, 348, 886.
[5]	Yan, G.; Yang, M. Org. Biomol. Chem. 2013, 11, 2554.
[6]	(a) Cadogan, J. I. G.; Todd, M. J. J. Chem. Soc. C 1969, 2808.
	(b) Sundberg, R. J. Tetrahedron Lett. 1966, 7, 477.
[7]	(a) Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035. pmid: 11848820
	(b) Ferretti, F.; Ramadan, D. R.; Ragaini, F. ChemCatChem 2019, 11, 4450. pmid: 11848820
[8]	(a) Rauser, M.; Eckert, R.; Gerbershagen, M.; Niggemann, M. Angew. Chem., Int. Ed. 2019, 58, 6713.
	(b) Li, C.; Wan, K.-F.; Guo, F.-Y.; Wu, Q.-H.; Yuan, M.-L.; Li, R.-X.; Fu, H.-Y.; Zheng, X.-L.; Chen, H. J. Org. Chem. 2019, 84, 2158.
	(c) Suárez-Pantiga, S.; Hernández-Ruiz, R.; Virumbrales, C.; Pedrosa, M. R.; Sanz, R. Angew. Chem., Int. Ed. 2019, 58, 2129.
[9]	(a) Cheung, C. W.; Ploeger, M. L.; Hu, X. Nat. Commun. 2017, 8, 14878. doi: 10.1038/ncomms14878 pmid: 28345585
	(b) Ploeger, M. L.; Darù, A.; Harvey, J. N.; Hu, X. ACS Catal. 2020, 10, 2845. pmid: 28345585
	(c) Cheung, C. W.; Shen, N.; Wang, S.-P.; Ullah, A.; Hu, X.; Ma, J.-A. Org. Chem. Front. 2019, 6, 756. doi: 10.1039/c8qo01405a pmid: 28345585
	(d) Peng, J.-B.; Geng, H.-Q.; Li, D.; Qi, X.; Ying, J.; Wu, X.-F. Org. Lett. 2018, 20, 4988. pmid: 28345585
[10]	Wang, X.; Yang, M.; Kuang, Y.; Liu, J.-B.; Fan, X.; Wu, J. Chem. Commun. 2020, 56, 3437.
[11]	(a) Yamamoto, Y.; Ohkubo, E.; Shibuya, M. Adv. Synth. Catal. 2017, 359, 1747.
	(b) Wu, Q.; Xu, G.; Li, W.; Wan, J.; Liu, T.; Huang, C. Org. Lett. 2022, 24, 3950.
	(c) Jana, N.; Zhou, F.; Driver, T. G. J. Am. Chem. Soc. 2015, 137, 6738.
[12]	Gao, Y.; Yang, S.; Huo, Y.; Hu, X.-Q. Adv. Synth. Catal. 2020, 362, 3971.
[13]	(a) Nykaza, T. V.; Cooper, J. C.; Li, G.; Mahieu, N.; Ramirez, A.; Luzung, M. R.; Radosevich, A. T. J. Am. Chem. Soc. 2018, 140, 15200.
	(b) Nykaza, T. V.; Harrison, T. S.; Ghosh, A.; Putnik, R. A.; Radosevich, A. T. J. Am. Chem. Soc. 2017, 139, 6839.
	(c) Massolo, E.; Pirola, M.; Puglisi, A.; Rossi, S.; Benaglia, M. RSC Adv. 2020, 10, 4040.
[14]	(a) Romero, K. J.; Galliher, M. S.; Pratt, D. A.; Stephenson, C. R. J. Chem. Soc. Rev. 2018, 47, 7851. doi: 10.1039/c8cs00379c pmid: 30101272
	(b) Yan, M.; Lo, J. C.; Edwards, J. T.; Baran, P. S. J. Am. Chem. Soc. 2016, 138, 12692. pmid: 30101272
	(c) Gu, Q.-S.; Li, Z.-L.; Liu, X.-Y. Acc. Chem. Res. 2020, 53, 170. pmid: 30101272
[15]	Zhao, H.; Cuomo, V. D.; Tian, W.; Romano, C.; Procter, D. J. Nat. Rev. Chem. 2024, 9, 61.
[16]	(a) Moshapo, P. T.; Simelane, S. B. ARKIVOC 2021, 2020, 190.
	(b) Zhu, H.; Driver, T. G. Synthesis 2022, 54, 3142.
	(c) Zou, D.; Wang, W.; Hu, Y.; Jia, T. Org. Biomol. Chem. 2023, 21, 2254.
[17]	(a) Teng, K.; Liu, Q.; Lv, J.; Li, T. ChemPhotoChem 2024, 8, e202300236.
	(b) Iizumi, K.; Yamaguchi, J. Org. Biomol. Chem. 2025, 23, 1746.
[18]	Aggarwal, V.; Bala, E.; Saima, S.; Pathan, S.; Guleria, S.; Sharma, S.; Selvaraj, M.; Verma, P. K. Synlett 2023, 35, 245.
[19]	(a) Abdel-Magid, A. F.; Mehrman, S. J. Org. Process Res. Dev. 2006, 10, 971.
	(b) Gomez, S.; Peters, J. A.; Maschmeyer, T. Adv. Synth. Catal. 2002, 344, 1037.
[20]	(a) Zhu, K.; Shaver, M. P.; Thomas, S. P. Chem. Sci. 2016, 7, 3031.
	(b) Zhu, K.; Shaver, M. P.; Thomas, S. P. Chem. Asian J. 2016, 11, 977.
[21]	Cheung, C. W.; Hu, X. Nat. Commun. 2016, 7, 12494. doi: 10.1038/ncomms12494 pmid: 27515391
[22]	Cheung, C. W.; Zhurkin, F. E.; Hu, X. J. Am. Chem. Soc. 2015, 137, 4932. doi: 10.1021/jacs.5b01784 pmid: 25831473
[23]	Itoh, T.; Nagata, K.; Miyazaki, M.; Ishikawa, H.; Kurihara, A.; Ohsawa, A. Tetrahedron 2004, 60, 6649.
[24]	Jiang, H.-M.; Qin, J.-H.; Sun, Q.; Zhang, D.; Jiang, J.-P.; Ouyang, X.-H.; Song, R.-J.; Li, J.-H. Org. Chem. Front. 2022, 9, 4070.
[25]	Li, G.; Yang, L.; Liu, J. J.; Zhang, W.; Cao, R.; Wang, C.; Zhang, Z.; Xiao, J.; Xue, D. Angew. Chem., Int. Ed. 2021, 60, 5230.
[26]	Bao, H.; Wang, L. Org. Lett. 2023, 25, 8872.
[27]	Wang, S.; Li, T.; Gu, C.; Han, J.; Zhao, C.-G.; Zhu, C.; Tan, H.; Xie, J. Nat. Commun. 2022, 13, 2432.
[28]	Ding, M.; Zhou, S.; Yao, S.; Zhu, C.; Li, W.; Xie, J. Chin. J. Chem. 2024, 42, 351.
[29]	Zhang, Z.-W.; Feng, Z.; Ma, J.-A.; Cheung, C. W. Nat. Synth. 2023, 2, 1171.
[30]	Zheng, T.; Feng, Z.; Ma, J.-A.; Cheung, C. W. Adv. Synth. Catal. 2023, 365, 2377.
[31]	Zhou, T.; Zhang, Z.-W.; Nie, J.; Kwong, F. Y.; Ma, J.-A.; Cheung, C. W. Nat. Commun. 2024, 15, 9926.
[32]	Panda, S.; Nanda, A.; Behera, R. R.; Ghosh, R.; Bagh, B. Chem. Commun. 2023, 59, 4527.
[33]	Wang, B.; Ma, J.; Ren, H.; Lu, S.; Xu, J.; Liang, Y.; Lu, C.; Yan, H. Chin. Chem. Lett. 2022, 33, 2420.
[34]	Kallitsakis, M. G.; Ioannou, D. I.; Terzidis, M. A.; Kostakis, G. E.; Lykakis, I. N. Org. Lett. 2020, 22, 4339. doi: 10.1021/acs.orglett.0c01367 pmid: 32453579
[35]	Waele, V. D.; Poizat, O.; Fagnoni, M.; Bagno, A.; Ravelli, D. ACS Catal. 2016, 6, 7174.
[36]	Wang, Q.; Ni, S.; Wang, X.; Wang, Y.; Pan, Y. Sci. China Chem. 2022, 65, 678.
[37]	(a) Zhang, W.; Lu, L.; Zhang, W.; Wang, Y.; Ware, S. D.; Mondragon, J.; Rein, J.; Strotman, N.; Lehnherr, D.; See, K. A.; Lin, S. Nature 2022, 604, 292.
	(b) Luo, J.; Davenport, M. T.; Ess, D. H.; Liu, T. L. Angew. Chem. Int. Ed. 2024, 63, e202407118.
[38]	Wang, Q.; Xu, J.; Xu, Z.; Wang, Z.; Tao, X.; Ni, S.; Pan, Y.; Wang, Y. Green Chem. 2023, 25, 7084.
[39]	Xiong, N.; Dong, Y.; Xu, B.; Li, Y.; Zeng, R. Org. Lett. 2022, 24, 4766.
[40]	Ning, Y.; Wang, S.; Li, M.; Han, J.; Zhu, C.; Xie, J. Nat. Commun. 2021, 12, 4637.
[41]	(a) Lücking, U. Org. Chem. Front. 2019, 6, 1319. pmid: 29364663
	(b) Petkowski, J. J.; Bains, W.; Seager, S. J. Nat. Prod. 2018, 81, 423. doi: 10.1021/acs.jnatprod.7b00921 pmid: 29364663
[42]	Feng, C.-W.; Wang, D.-Y.; Lu, H.-L.; Xi, Z.-W.; Shen, Y.-M.; Cao, J. Org. Lett. 2022, 24, 4485.
[43]	(a) Gannon, M. K., II; Holt, J. J.; Bennett, S. M.; Wetzel, B. R.; Loo, T. W.; Bartlett, M. C.; Clarke, D. M.; Sawada, G. A.; Higgins, J. W.; Tombline, G.; Raub, T. J.; Detty, M. R. J. Med. Chem. 2009, 52, 3328.
	(b) Chen, X.; Mietlicki-Baase, E. G.; Barrett, T. M.; McGrath, L. E.; Koch-Laskowski, K.; Ferrie, J. J.; Hayes, M. R.; Petersson, E. J. J. Am. Chem. Soc. 2017, 139, 16688.
[44]	Do, N. T.; Tran, K. M.; Phan, H. T.; To, T. A.; Nguyen, T. T.; Phan, N. T. S. Org. Biomol. Chem. 2019, 17, 8987.
[45]	Barak, D. S.; Dahatonde, D. J.; Dighe, S. U.; Kant, R.; Batra, S. Org. Lett. 2020, 22, 9381.
[46]	(a) Mukhopadhyay, S.; Barak, D. S.; Avasthi, I.; Batra, S. Adv. Synth. Catal. 2017, 359, 4050.
	(b) Barak, D. S.; Dahatonde, D. J.; Batra, S. Asian J. Org. Chem. 2019, 8, 2149.
[47]	Lu, C.; Su, Z.; Jing, D.; Jin, S.; Xie, L.; Li, L.; Zheng, K. Org. Lett. 2019, 21, 1438.
[48]	Sun, B.; Lv, C.; Zhuang, X.; Xu, Y.; Song, H.; Wang, J.; Zhang, Z.; Wang, J.; Jin, C. Green Chem. 2024, 26, 11531.
[49]	Guo, J.; Xie, Y.; Zeng, W.-T.; Wu, Q.-L.; Weng, J.; Lu, G. Adv. Synth. Catal. 2020, 362, 5450.
[50]	Li, M.; Zhao, M.; Zhong, X.; Wen, X.; Liu, X.; Jiang, H.; Tan, R.; Li, J. Org. Chem. Front. 2025, 12, 636.
[51]	Wang, B.; Zhou, M.-J.; Zhou, Q.-L. Org. Lett. 2022, 24, 2894.
[52]	Shao, X.-Z.; Xu, G.-Y.; Fan, W.; Zhang, S.; Li, M.-B. Org. Chem. Front. 2023, 10, 624.
[53]	Zhou, Y.; He, Y.; Huang, H.; Deng, G.-J. Org. Biomol. Chem. 2025, 23, 1338.
[54]	(a) Chang, L.; An, Q.; Duan, L.; Feng, K.; Zuo, Z. Chem. Rev. 2022, 122, 2429.
	(b) Hu, A.; Guo, J.-J.; Pan, H.; Zuo, Z. Science 2018, 361, 668.
[55]	Colgan, A. C.; Proctor, R. S. J.; Gibson, D. C.; Chuentragool, P.; Lahdenperä, A. S. K.; Ermanis, K.; Phipps, R. J. Angew. Chem. Int. Ed. 2022, 61, e202200266.
[56]	Wang, B.; Ren, H.; Cao, H.-J.; Lu, C.; Yan, H. Chem. Sci. 2022, 13, 11074. doi: 10.1039/d2sc03590a pmid: 36320483
[57]	Weintraub, P. M.; Sabol, J. S.; Kane, J. M.; Borcherding, D. R. Tetrahedron 2003, 59, 2953.
[58]	Duttwyler, S.; Chen, S.; Takase, M. K.; Wiberg, K. B.; Bergman, R. G.; Ellman, J. A. Science 2013, 339, 678. doi: 10.1126/science.1230704 pmid: 23393259
[59]	Mykura, R.; Sánchez-Bento, R.; Matador, E.; Duong, V. K.; Varela, A.; Angelini, L.; Carbajo, R. J.; Llaveria, J.; Ruffoni, A.; Leonori, D. Nat. Chem. 2024, 16, 771.
[60]	Pham, H. T.; Ho, T. H.; Do, D. Q.; Nguyen, K. L. H.; Nguyen, T. T.; Phan, N. T. S. Synlett 2020, 31, 1813.
[61]	Nguyen, T. B.; Ermolenko, L.; Al-Mourabit, A. Org. Lett. 2013, 15, 4218. doi: 10.1021/ol401944a pmid: 23924277
[62]	Zou, D.; Gan, L.; Yang, F.; Wang, H.; Pu, Y.; Li, J.; Walsh, P. J. Nat. Commun. 2021, 12, 7060.
[63]	(a) Li, M.; Berritt, S.; Matuszewski, L.; Deng, G.; Pascual-Escudero, A.; Panetti, G. B.; Poznik, M.; Yang, X.; Chruma, J. J.; Walsh, P. J. J. Am. Chem. Soc. 2017, 139, 16327.
	(b) Li, M.; Gutierrez, O.; Berritt, S.; Pascual-Escudero, A.; Yeşilçimen, A.; Yang, X.; Adrio, J.; Huang, G.; Nakamaru-Ogiso, E.; Kozlowski, M. C.; Walsh, P. J. Nat. Chem. 2017, 9, 997.
	(c) Zou, D.; Wang, W.; Ying, J. Adv. Synth. Catal. 2024, 366, 1450.
[64]	Stateman, L. M.; Nakafuku, K. M.; Nagib, D. A. Synthesis 2018, 50, 1569.
[65]	Chen, Z.-M.; Zhang, X.-M.; Tu, Y.-Q. Chem. Soc. Rev. 2015, 44, 5220.
[66]	White, N. A.; Rovis, T. J. Am. Chem. Soc. 2014, 136, 14674.
[67]	(a) Zięba-Mizgała, A.; Puszko, A.; Regiec, A.; Kuduk-Jaworska, J. Bioelectrochemistry 2005, 65, 113. pmid: 22548244
	(b) DiRocco, D. A.; Rovis, T. J. Am. Chem. Soc. 2012, 134, 8094. doi: 10.1021/ja3030164 pmid: 22548244
[68]	Zhang, Y.; Du, Y.; Huang, Z.; Xu, J.; Wu, X.; Wang, Y.; Wang, M.; Yang, S.; Webster, R. D.; Chi, Y. R. J. Am. Chem. Soc. 2015, 137, 2416.
[69]	Wang, H.; Wang, Y.; Chen, X.; Mou, C.; Yu, S.; Chai, H.; Jin, Z.; Chi, Y. R. Org. Lett. 2019, 21, 7440.
[70]	Bhunia, A.; Bergander, K.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2021, 60, 8313.
[71]	Elfert, J.; Bhunia, A.; Daniliuc, C. G.; Studer, A. ACS Catal. 2023, 13, 6704.
[72]	Stefanow, V.; Grandane, A.; Eh, M.; Panten, J.; Spannenberg, A.; Werner, T. Org. Process Res. Dev. 2021, 25, 89.
[73]	Hampton, C.; Simonetti, M.; Leonori, D. Angew. Chem., Int. Ed. 2023, 62, e202214508.
[74]	Paolillo, J. M.; Duke, A. D.; Gogarnoiu, E. S.; Wise, D. E.; Parasram, M. J. Am. Chem. Soc. 2023, 145, 2794.
[75]	Wise, D. E.; Gogarnoiu, E. S.; Duke, A. D.; Paolillo, J. M.; Vacala, T. L.; Hussain, W. A.; Parasram, M. J. Am. Chem. Soc. 2022, 144, 15437. doi: 10.1021/jacs.2c05648 pmid: 35930615
[76]	Buchi, G.; Ayer, D. E. J. Am. Chem. Soc. 1956, 78, 689.
[77]	Ruffoni, A.; Hampton, C.; Simonetti, M.; Leonori, D. Nature 2022, 610, 81.
[78]	Göttemann, L. T.; Wiesler, S.; Sarpong, R. Chem. Sci. 2024, 15, 213.
[79]	Shah, J. A.; Banerjee, A.; Mukherjee, U.; Ngai, M.-Y. Chem 2024, 10, 686.
[80]	Liu, X.; Hu, Z.; Portela, B. S.; Rettner, E. M.; Pineda, A.; Miscall, J.; Rorrer, N. A.; Krummel, A. T.; Paton, R. S.; Miyake, G. M. Angew. Chem., Int. Ed. 2025, 64, e202418411.
[81]	(a) Iwasaki, M.; Ikemoto, Y.; Nishihara, Y. Org. Lett. 2020, 22, 7577.
	(b) Tsuchiya, Y.; Onai, R.; Uraguchi, D.; Ooi, T. Chem. Commun. 2020, 56, 11014.
[82]	(a) Zhang, Z.; Yue, S.; Jin, B.; Yang, R.; Wang, S.; Zhang, T.; Sun, L.; Lei, A.; Cai, H. Nat. Commun. 2024, 15, 4186. doi: 10.1038/s41467-024-48540-6 pmid: 38760336
	(b) Li, J.; Zou, D.; Wang, B.; İşcan, A.; Jin, H.; Chen, L.; Zhou, F.; Walsh, P. J.; Liang, G. Org. Chem. Front. 2022, 9, 3854. pmid: 38760336
[83]	(a) Mo, K.; Zhou, X.; Wu, J.; Zhao, Y. Chem. Commun. 2022, 58, 1306.
	(b) Duff, L.; Meakin, H.; Richardson, A.; Greener, A. J.; Smith, G. W. A.; Ocaña, I.; Chechik, V.; James, M. J. Chem.-Eur. J. 2023, 29, e202203807.