Selective Functionalization of C(sp3)—H Bonds via Photoredox/ Nickel Dual Catalysis

doi:10.6023/cjoc202406036

Abstract

The conversion of readily available hydrocarbons into high value-added chiral compounds via C(sp³)—H functionalization has attracted a great deal of interest from both academia and industry. This transformation is undoubtedly a revolutionary approach due to its inherent atom and step economy, as well as the abundance of starting materials. Classical transition- metal-catalyzed C—H activation usually requires noble metal catalysts, high temperatures, and coordinated directing groups. In recent years, the rapid development of the field of photocatalysis has provided new methods for the activation of inert C(sp³)—H bonds. The combination of photoinduced C(sp³)—H bond cleavage and nickel-catalyzed cross-coupling reactions has emerged as a powerful tool for the selective functionalization of C(sp³)—H bonds. Herein, the recent progress in selective C(sp³)—H functionalization via photoredox/nickel dual catalysis is summarized.

Key words: photoredox/nickel dual catalysis, C(sp³)—H bonds, hydrogen atom transfer, cross-coupling reactions

Cite this article

Xiaoqin Wang, Sheng Xu, Yuanyuan Ping, Wangqing Kong. Selective Functionalization of C(sp³)—H Bonds via Photoredox/ Nickel Dual Catalysis[J]. Chinese Journal of Organic Chemistry, 2025, 45(2): 383-422.

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Fig. & Tab. 53

Scheme 1. Classical Ni-catalyzed vs. Ni-photoredox catalyzed coupling reaction

Scheme 2. Four models of nickel-photoredox catalysis

Scheme 3. C(sp3)—H arylation of dimethyl anilines

Scheme 4. C(sp3)—H bond arylation/alkenylation of anilines

Scheme 5. C(sp3)—H bond acylation of anilines

Scheme 6. C(sp3)—H arylation/acylation of indoles

Scheme 7. 1,4-Dicarbofunctionalization of 1,3-enynes

Scheme 8. Arylation of allylic C(sp3)—H bonds

Scheme 9. Arylation of C(sp3)—H bonds using quinuclidine as HAT reagent

Scheme 10. Arylation of amide using phenols as aryl sources

Scheme 11. Alkylation of C(sp3)—H bonds using amine/sulfamate as HAT reagents

Scheme 12. Oxy-functionalization of benzylic C(sp3)—H bonds

Scheme 13. C(sp3)—H bonds functionalizations using amide/sulfamate as intramolecular HAT reagent

Scheme 14. C(sp3)—H bond arylation and alkylation of amides

Scheme 15. Cross-dehydrogenative coupling of aldehyde with benzylic C(sp3)—H bonds

Scheme 16. Dehydrogenative coupling with primary alcohols

Scheme 17. Cross coupling of benzylic C(sp3)—H with acyl chlorides

Scheme 18. Carbamoylation of benzylic C(sp3)—H bonds with isocyanates

Scheme 19. Photoredox/nickel dual-catalyzed stereoselective arylation of allylic C(sp3)—H bonds

Scheme 20. Photoredox/nickel dual-catalyzed methylation of C(sp3)—H bonds using peroxides

Scheme 21. Arylation of allylic C(sp3)—H bonds using thiophosphoric imide as HAT reagent

Scheme 22. Arylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

Scheme 23. Acylation/alkynylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

Scheme 24. Alkylation of allylic C(sp3)—H bonds using TBADT

Scheme 25. Alkylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

Scheme 26. Methylation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

Scheme 27. Amination/amidation of C(sp3)—H bonds using TBADT as photoinduced HAT reagent

Scheme 28. Dicarbofunctionalization of olefins

Scheme 29. 1,4-DCF of 1,3-enynes using TBADT as photoinduced HAT reagent

Scheme 30. Mechanism of diaryl ketones as photoinduced HAT reagent

Scheme 31. Arylation/alkylation of C(sp3)—H bonds using diaryl ketone as photoinduced HAT reagent

Scheme 32. Carbofunctionalization of benzylic C(sp3)—H bonds

Scheme 33. Three-component cross-coupling reaction of C(sp3)—H, alkene and aryl bromide

Scheme 34. Arylation/alkylation of C(sp3)—H bonds using benzaldehyde as photoinduced HAT reagent

X	E⁰(X·/X^—)^a/V	BDE (H—X)/(kJ/mol)
Cl	＋2.03	432
Br	＋1.60	369

Table 1. Redox potential of X·/X— and the BDE of H—X bond

Scheme 35. Molander group: arylation of α-alkoxy C(sp3)—H bonds

Scheme 36. Bromine radical mediate functionalization of C(sp3)—H bonds

Scheme 37. C(sp3)—H arylation of ethers

Scheme 38. C(sp3)—H arylation of amides

Scheme 39. Hydroalkylation of alkynes

Scheme 40. Acylation of C(sp3)—H bonds

Scheme 41. Other C(sp3)—H acylation reactions

Scheme 42. Photoredox/nickel dual-catalyzed asymmetric C(sp3)—H arylation

Scheme 43. Photoredox/nickel dual-catalyzed asymmetric arylation of benzylic C(sp3)—H bonds

Scheme 44. Photoredox/nickel dual-catalyzed asymmetric alkenylation of benzylic C(sp3)—H bonds

Scheme 45. Photoredox/nickel dual-catalyzed asymmetric arylation of α-amino C(sp3)—H bonds

Scheme 46. Asymmetric arylation/alkenylation of oxacycles C(sp3)—H bonds

Scheme 47. Asymmetric acylation of benzamides C(sp3)—H bonds

Scheme 48. Asymmetric acylation of benzylic C(sp3)—H bonds

Scheme 49. Asymmetric acylation of saturated N-heterocycles C(sp3)—H bonds

Scheme 50. Asymmetric carbamoylation of benzylic C(sp3)—H bonds with isocyanates

Scheme 51. Asymmetric alkylation of amide C(sp3)—H bonds

Scheme 52. Three-component asymmetric coupling of C(sp3)—H, olefin, and Ar-Br

References 123

[1]	Lovering, F. MedChemComm 2013, 4, 515.
[2]	Rudolph, A.; Lautens, M. Angew. Chem. Int. Ed. 2009, 48, 2656. doi: 10.1002/anie.200803611 pmid: 19173365
[3]	Choi, J.; Fu, G. C. Science 2017, 356, eaaf7230.
[4]	Tasker, S. Z.; Standley, E. A.; Jamison, T. F. Nature 2014, 509, 299.
[5]	Diccianni, J. B.; Diao, T. Trends Chem. 2019, 1, 830.
[6]	Chan, A. Y.; Perry, I. B.; Bissonnette, N. B.; Buksh, B. F.; Edwards, G. A.; Frye, L. I.; Garry, O. L.; Lavagnino, M. N.; Li, B. X.; Liang, Y.; Mao, E.; Millet, A.; Oakley, J. V.; Reed, N. L.; Sakai, H. A.; Seath, C. P.; MacMillan, D. W. C. Chem. Rev. 2022, 122, 1485.
[7]	Li, Z.; Li, C.; Ding, Y.; Huo, H., Coord. Chem. Rev. 2022, 460, 214479.
[8]	Zuo, Z.; Ahneman, D. T.; Chu, L.; Terrett, J. A.; Doyle, A. G.; MacMillan, D. W. C. Science 2014, 345, 437.
[9]	Tellis, J. C.; Primer, D. N.; Molander, G. A. Science 2014, 345, 433. doi: 10.1126/science.1253647 pmid: 24903560
[10]	Corcé, V.; Chamoreau, L.-M.; Derat, E.; Goddard, J.-P.; Ollivier, C.; Fensterbank, L. Angew. Chem. Int. Ed. 2015, 54, 11414.
[11]	Gutiérrez-Bonet, Á.; Tellis, J. C.; Matsui, J. K.; Vara, B. A.; Molander, G. A. ACS Catal. 2016, 6, 8004. pmid: 27990318
[12]	Zhang, X.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 13862.
[13]	Vara, B. A.; Patel, N. R.; Molander, G. A. ACS Catal. 2017, 7, 3955.
[14]	Smith, R. T.; Zhang, X.; Rincón, J. A.; Agejas, J.; Mateos, C.; Barberis, M.; García-Cerrada, S.; de Frutos, O.; MacMillan, D. W. C. J. Am. Chem. Soc. 2018, 140, 17433
[15]	Dong, Z.; MacMillan, D. W. C. Nature 2021, 598, 451.
[16]	Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[17]	Romero, N. A.; Nicewicz, D. A. Chem. Rev. 2016, 116, 10075.
[18]	Bellotti, P.; Huang, H.-M.; Faber, T.; Glorius, F. Chem. Rev. 2023, 123, 4237.
[19]	Qin, Q.; Jiang, H.; Hu, Z.; Ren, D.; Yu, S. Chem. Rec. 2017, 17, 754.
[20]	Cao, H.; Tang, X.; Tang, H.; Yuan, Y.; Wu, J. Chem Catal. 2021, 1, 523.
[21]	Capaldo, L.; Ravelli, D.; Fagnoni, M. Chem. Rev. 2022, 122, 1875.
[22]	Zhang, J.; Rueping, M. Chem. Soc. Rev. 2023, 52, 4099.
[23]	McNally, A.; Prier, C. K.; MacMillan, D. W. C. Science 2011, 334, 1114. doi: 10.1126/science.1213920 pmid: 22116882
[24]	Ahneman, D. T.; Doyle, A. G. Chem. Sci. 2016, 7, 7002. doi: 10.1039/C6SC02815B pmid: 28058105
[25]	Gui, Y.-Y.; Wang, Z.-X.; Zhou, W.-J.; Liao, L.-L.; Song, L.; Yin, Z.-B.; Li, J.; Yu, D.-G. Asian J. Org. Chem. 2018, 7, 537.
[26]	Gui, Y.-Y.; Liao, L.-L.; Sun, L.; Zhang, Z.; Ye, J.-H.; Shen, G.; Lu, Z.-P.; Zhou, W.-J.; Yu, D.-G. Chem. Commun. 2017, 53, 1192.
[27]	Joe, C. L.; Doyle, A. G. Angew. Chem. Int. Ed. 2016, 55, 4040.
[28]	Kim, W.; Koo, J.; Lee, H. G. Chem. Sci. 2021, 12, 4119.
[29]	Cheng, C.; Lv, G.-F.; Wu, S.; Li, Y.; Li, J.-H. Org. Lett. 2023, 25, 4236.
[30]	Liu, K.; Studer, A. Angew. Chem. Int. Ed. 2022, 61, e202206533.
[31]	Cannalire, R.; Pelliccia, S.; Sancineto, L.; Novellino, E.; Tron, G. C.; Giustiniano, M. Chem. Soc. Rev. 2021, 50, 766. doi: 10.1039/d0cs00493f pmid: 33350402
[32]	Rosemann, N. W.; Eußner, J. P.; Beyer, A.; Koch, S. W.; Volz, K.; Dehnen, S.; Chatterjee, S. Science 2016, 352, 1301. doi: 10.1126/science.aaf6138 pmid: 27284190
[33]	Maity, B.; Zhu, C.; Yue, H.; Huang, L.; Harb, M.; Minenkov, Y.; Rueping, M.; Cavallo, L. J. Am. Chem. Soc. 2020, 142, 16942.
[34]	Twilton, J.; Christensen, M.; DiRocco, D. A.; Ruck, R. T.; Davies, I. W.; MacMillan, D. W. C. Angew. Chem. Int. Ed. 2018, 57, 5369. doi: 10.1002/anie.201800749 pmid: 29490112
[35]	Gui, Y.-Y.; Chen, X.-W.; Zhou, W.-J.; Yu, D.-G. Synlett 2017, 28, 2581.
[36]	Le, C.; Liang, Y.; Evans, R. W.; Li, X.; MacMillan, D. W. C. Nature 2017, 547, 79.
[37]	Ma, Z.-Y.; Li, M.; Guo, L.-N.; Liu, L.; Wang, D.; Duan, X.-H. Org. Lett. 2021, 23, 474.
[38]	Dong, M.; Jia, Y.; Zhou, W.; Gao, J.; Lv, X.; Luo, F.; Zhang, Y.; Liu, S. Org. Chem. Front. 2021, 8, 6881.
[39]	Chu, J. C. K.; Rovis, T. Nature 2016, 539, 272.
[40]	Choi, G. J.; Zhu, Q.; Miller, D. C.; Gu, C. J.; Knowles, R. R. Nature 2016, 539, 268.
[41]	Thullen, S. M.; Treacy, S. M.; Rovis, T. J. Am. Chem. Soc. 2019, 141, 14062. doi: 10.1021/jacs.9b07014 pmid: 31478370
[42]	Xu, B.; Tambar, U. K. ACS Catal. 2019, 9, 4627.
[43]	Kanegusuku, A. L. G.; Castanheiro, T.; Ayer, S. K.; Roizen, J. L. Org. Lett. 2019, 21, 6089. doi: 10.1021/acs.orglett.9b02234 pmid: 31313933
[44]	Simons, R. T.; Nandakumar, M.; Kwon, K.; Ayer, S. K.; Venneti, N. M.; Roizen, J. L. J. Am. Chem. Soc. 2023, 145, 3882.
[45]	Zhang, P.; Le, C. C.; MacMillan, D. W. C. J. Am. Chem. Soc. 2016, 138, 8084.
[46]	Wang, Z.; Ji, X.; Han, T.; Deng, G.-J.; Huang, H. Adv. Synth. Catal. 2019, 361, 5643.
[47]	Rand, A. W.; Yin, H.; Xu, L.; Giacoboni, J.; Martin-Montero, R.; Romano, C.; Montgomery, J.; Martin, R. ACS Catal. 2020, 10, 4671.
[48]	Yue, W.-J.; Day, C. S.; Martin, R. J. Am. Chem. Soc. 2021, 143, 6395.
[49]	Rand, A. W.; Chen, M.; Montgomery, J. Chem. Sci. 2022, 13, 10566.
[50]	Kawasaki, T.; Ishida, N.; Murakami, M. J. Am. Chem. Soc. 2020, 142, 3366. doi: 10.1021/jacs.9b13920 pmid: 32011871
[51]	Griffiths, O. M.; Esteves, H. A.; Chen, Y.; Sowa, K.; May, O. S.; Morse, P.; Blakemore, D. C.; Ley, S. V. J. Org. Chem. 2021, 86, 13559. doi: 10.1021/acs.joc.1c01621 pmid: 34524825
[52]	Ishida, N.; Son, M.; Kawasaki, T.; Ito, M.; Murakami, M. Synlett 2021, 32, 2067.
[53]	Ishida, N.; Shinoya, H.; Kamino, Y.; Kawasaki, T.; Murakami, M. Chem. Lett. 2022, 51, 765.
[54]	Kawasaki, T.; Tosaki, T.; Ishida, N.; Murakami, M. Org. Lett. 2021, 23, 7683.
[55]	Kawasaki, T.; Tosaki, T.; Miki, S.; Takada, T.; Murakami, M.; Ishida, N. J. Am. Chem. Soc. 2024, 146, 17566.
[56]	Wang, Q.-L.; Huang, H.; Mao, G.; Deng, G.-J. Green Chem. 2022, 24, 8324.
[57]	Kawasaki, T.; Yamazaki, K.; Tomono, R.; Ishida, N.; Murakami, M. Chem. Lett. 2021, 50, 1684. doi: 10.1246/cl.210333
[58]	Huang, L.; Szewczyk, M.; Kancherla, R.; Maity, B.; Zhu, C.; Cavallo, L.; Rueping, M. Nat. Commun. 2023, 14, 548. doi: 10.1038/s41467-023-36103-0 pmid: 36725849
[59]	Yi, H.; Zhang, G.; Wang, H.; Huang, Z.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016.
[60]	Scaiano, J. C.; Wubbels, G. G. J. Am. Chem. Soc. 1981, 103, 640.
[61]	Vasilopoulos, A.; Krska, S. W.; Stahl, S. S. Science 2021, 372, 398. doi: 10.1126/science.abh2623 pmid: 33888639
[62]	Gong, Y.; Su, L.; Zhu, Z.; Ye, Y.; Gong, H. Angew. Chem. Int. Ed. 2022, 61, e202201662.
[63]	Chen, M.; Ventura, A. M.; Das, S.; Ibrahim, A. F.; Zimmerman, P. M.; Montgomery, J. J. Am. Chem. Soc. 2023, 145, 20176. doi: 10.1021/jacs.3c06532 pmid: 37672664
[64]	Kato, S.; Saga, Y.; Kojima, M.; Fuse, H.; Matsunaga, S.; Fukatsu, A.; Kondo, M.; Masaoka, S.; Kanai, M. J. Am. Chem. Soc. 2017, 139, 2204.
[65]	Huang, H.-M.; Bellotti, P.; Chen, P.-P.; Houk, K. N.; Glorius, F. Nat. Synth. 2022, 1, 59.
[66]	Ravelli, D.; Fagnoni, M.; Fukuyama, T.; Nishikawa, T.; Ryu, I. ACS Catal. 2018, 8, 701.
[67]	Perez-Prieto, J.; Galian, R.; Miranda, M. Mini-Rev. Org. Chem 2006, 3, 117.
[68]	Waele, V. D.; Poizat, O.; Fagnoni, M.; Bagno, A.; Ravelli, D. ACS Catal. 2016, 6, 7174.
[69]	Perry, I. B.; Brewer, T. F.; Sarver, P. J.; Schultz, D. M.; DiRocco, D. A.; MacMillan, D. W. C. Nature 2018, 560, 70.
[70]	Mazzarella, D.; Pulcinella, A.; Bovy, L.; Broersma, R.; Noël, T. Angew. Chem. Int. Ed. 2021, 60, 21277. doi: 10.1002/anie.202108987 pmid: 34329531
[71]	Liu, W.; Ke, Y.; Liu, C.; Kong, W. Chem. Commun. 2022, 58, 11937.
[72]	Jin, Y.; Ng, E. W. H.; Fan, T.; Hirao, H.; Gong, L.-Z. ACS Catal. 2022, 12, 10039.
[73]	Pilli, R.; Selvam, K.; Balamurugan, B. S. S.; Jose, V.; Rasappan, R. Org. Lett. 2024, 26, 2993.
[74]	Hu, Z.; Wang, D.; Xu, T. ACS Catal. 2024, 14, 547.
[75]	Bour, J. R.; Ferguson, D. M.; McClain, E. J.; Kampf, J. W.; Sanford, M. S. J. Am. Chem. Soc. 2019, 141, 8914.
[76]	Tsymbal, A. V.; Bizzini, L. D.; MacMillan, D. W. C. J. Am. Chem. Soc. 2022, 144, 21278. doi: 10.1021/jacs.2c08989 pmid: 36375080
[77]	Mao, E.; MacMillan, D. W. C. J. Am. Chem. Soc. 2023, 145, 2787.
[78]	Wang, Q.; Ni, S.; Yu, L.; Pan, Y.; Wang, Y. ACS Catal. 2022, 12, 11071.
[79]	Zhou, S.; Liu, T.; Bao, X. J. Catal. 2022, 415, 142.
[80]	Xu, L., F., W., Chen, F., Zhu, S., Chu, L. Chin. J. Org. Chem. 2022, 42, 1.
[81]	Xu, S.; Chen, H.; Zhou, Z.; Kong, W. Angew. Chem. Int. Ed. 2021, 60, 7405.
[82]	Wang, D.; Ackermann, L. Chem. Sci. 2022, 13, 7256.
[83]	Liu, W.; Liu, C.; Wang, M.; Kong, W. ACS Catal. 2022, 12, 10207.
[84]	Wagner, P. J.; Kemppainen, A. E.; Schott, H. N. J. Am. Chem. Soc. 1970, 92, 5280.
[85]	Péter, Á.; Agasti, S.; Knowles, O.; Pye, E.; Procter, D. J. Chem. Soc. Rev. 2021, 50, 5349. doi: 10.1039/d0cs00358a pmid: 33972956
[86]	Shen, Y.; Gu, Y.; Martin, R. J. Am. Chem. Soc. 2018, 140, 12200.
[87]	Dewanji, A.; Krach, P. E.; Rueping, M. Angew. Chem. Int. Ed. 2019, 58, 3566.
[88]	Krach, P. E.; Dewanji, A.; Yuan, T.; Rueping, M. Chem. Commun. 2020, 56, 6082.
[89]	Ren, C.-C.; Wang, T.-Q.; Zhang, Y.; Peng, D.; Liu, X.-Q.; Wu, Q.-A.; Liu, X.-F.; Luo, S.-P. ChemistrySelect 2021, 6, 2523.
[90]	Ishida, N.; Masuda, Y.; Imamura, Y.; Yamazaki, K.; Murakami, M. J. Am. Chem. Soc. 2019, 141, 19611. doi: 10.1021/jacs.9b12529 pmid: 31775498
[91]	Xu, Z.; Liu, D.; Yu, H.; Ahlquist, M. S. G.; Fu, Y. Mol. Catal. 2021, 514, 111785.
[92]	Campbell, M. W.; Yuan, M.; Polites, V. C.; Gutierrez, O.; Molander, G. A. J. Am. Chem. Soc. 2021, 143, 3901. doi: 10.1021/jacs.0c13077 pmid: 33660996
[93]	Zhang, L.; Si, X.; Yang, Y.; Zimmer, M.; Witzel, S.; Sekine, K.; Rudolph, M.; Hashmi, A. S. K. Angew. Chem. Int. Ed. 2019, 58, 1823.
[94]	Si, X.; Zhang, L.; Hashmi, A. S. K. Org. Lett. 2019, 21, 6329.
[95]	Heitz, D. R.; Tellis, J. C.; Molander, G. A. J. Am. Chem. Soc. 2016, 138, 12715. pmid: 27653500
[96]	Ishida, N.; Masuda, Y.; Ishikawa, N.; Murakami, M. Asian J. Org. Chem. 2017, 6, 669.
[97]	Huang, L.; Rueping, M. Angew. Chem. Int. Ed. 2018, 57, 10333. doi: 10.1002/anie.201805118 pmid: 30011106
[98]	Santos, M. S.; Corrêa, A. G.; Paixão, M. W.; König, B. Adv. Synth. Catal. 2020, 362, 2367.
[99]	Kancherla, R.; Muralirajan, K.; Maity, B.; Karuthedath, S.; Kumar, G. S.; Laquai, F.; Cavallo, L.; Rueping, M. Nat. Commun. 2022, 13, 2737. doi: 10.1038/s41467-022-30278-8 pmid: 35585041
[100]	Shields, B. J.; Doyle, A. G. J. Am. Chem. Soc. 2016, 138, 12719.
[101]	Nielsen, M. K.; Shields, B. J.; Liu, J.; Williams, M. J.; Zacuto, M. J.; Doyle, A. G. Angew. Chem. Int. Ed. 2017, 56, 7191.
[102]	Cai, Y.; Tang, Y.; Fan, L.; Lefebvre, Q.; Hou, H.; Rueping, M. ACS Catal. 2018, 8, 9471.
[103]	Das, S.; Murugesan, K.; Villegas Rodríguez, G. J.; Kaur, J.; Barham, J. P.; Savateev, A.; Antonietti, M.; König, B. ACS Catal. 2021, 11, 1593.
[104]	Deng, H.-P.; Fan, X.-Z.; Chen, Z.-H.; Xu, Q.-H.; Wu, J. J. Am. Chem. Soc. 2017, 139, 13579.
[105]	Go, S. Y.; Lee, G. S.; Hong, S. H. Org. Lett. 2018, 20, 4691.
[106]	Ackerman, L. K. G.; Martinez Alvarado, J. I.; Doyle, A. G. J. Am. Chem. Soc. 2018, 140, 14059. doi: 10.1021/jacs.8b09191 pmid: 30351143
[107]	Sun, Z.; Kumagai, N.; Shibasaki, M. Org. Lett. 2017, 19, 3727.
[108]	Lee, G. S.; Won, J.; Choi, S.; Baik, M.-H.; Hong, S. H. Angew. Chem. Int. Ed. 2020, 59, 16933.
[109]	Zhang, J.; Niu, Y.; Kong, F.; Yan, M. J. Catal. 2022, 416, 58.
[110]	Lee, G. S.; Park, B.; Hong, S. H. Nat. Commun. 2022, 13, 5200.
[111]	Xu, G.-Q.; Wang, W. D.; Xu, P.-F. J. Am. Chem. Soc. 2024, 146, 1209.
[112]	Cheng, X.; Lu, H.; Lu, Z. Nat. Commun. 2019, 10, 3549.
[113]	Zhang, W.; Shu, X.; Huan, L.; Cheng, B.; Huo, H. Org. Biomol. Chem. 2021, 19, 9407. doi: 10.1039/d1ob01774h pmid: 34708852
[114]	Cheng, X.; Li, T.; Liu, Y.; Lu, Z. ACS Catal. 2021, 11, 11059.
[115]	Xu, J.; Li, Z.; Xu, Y.; Shu, X.; Huo, H. ACS Catal. 2021, 11, 13567.
[116]	Shu, X.; Zhong, D.; Lin, Y.; Qin, X.; Huo, H. J. Am. Chem. Soc. 2022, 144, 8797.
[117]	Xu, S.; Ping, Y.; Li, W.; Guo, H.; Su, Y.; Li, Z.; Wang, M.; Kong, W. J. Am. Chem. Soc. 2023, 145, 5231.
[118]	Shu, X.; Huan, L.; Huang, Q.; Huo, H. J. Am. Chem. Soc. 2020, 142, 19058.
[119]	Huan, L.; Shu, X.; Zu, W.; Zhong, D.; Huo, H. Nat. Commun. 2021, 12, 3536.
[120]	Shu, X.; Zhong, D.; Huang, Q.; Huan, L.; Huo, H. Nat. Commun 2023, 14, 125.
[121]	Cuesta-Galisteo, S.; Schörgenhumer, J.; Hervieu, C. Nevado, C. Angew. Chem. Int. Ed. 2024, 63, e202313717.
[122]	Li, J.; Cheng, B.; Shu, X.; Xu, Z.; Li, C.; Huo, H. J. Am. Chem. Soc. 2024, 146, 19909.
[123]	Hu, X.; Cheng-Sánchez, I.; Kong, W.; Molander, G. A. Nevado, C., Nat. Catal. 2024, 7, 655.

光/镍协同催化实现C(sp³)—H键选择性官能团化

Selective Functionalization of C(sp³)—H Bonds via Photoredox/ Nickel Dual Catalysis

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[7]	Panpan Lei, Qinlin Chen, Hang Chen, Yang Zhou, Linhai Jin, Wei Wang, Fener Chen. Synthesis of Bibenzyl Derivatives via Visible-Light-Promoted 1,5-Hydrogen Atom Transfer/Radical Coupling Reactions of N-Fluorocarboxamides [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 254-264.
[8]	Peng Pan, Qiyang Yuan, Shihui Liu, Jianhong Zhao, Yongqiang Zhang. Research of Quinuclidine-Promoted C—H Silylation of Electron- Deficient Nitrogen Heteroarenes [J]. Chinese Journal of Organic Chemistry, 2022, 42(4): 1136-1145.
[9]	Baitong Yue, Xinxin Wu, Chen Zhu. Recent Advances in Vinyl Radical-Mediated Hydrogen Atom Transfer [J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 458-470.
[10]	Liang Wu, Hanlin Wei, Jianzhong Chen, Wanbin Zhang. Development of Nickel-Catalyzed Cross-Coupling of Alcohol Derivatives to Construct Carbon-Carbon Bonds [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4208-4239.
[11]	Yuan Xiaoya, Yang Guoping, Yu Bing. Photoinduced Decatungstate-Catalyzed C-H Functionalization [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3620-3632.
[12]	Kong Lichun, Zhou Yulu, Luo Fang, Zhu Gangguo. Recent Advances on Oxidative Radical Addition to Aldehydes [J]. Chin. J. Org. Chem., 2018, 38(11): 2858-2865.
[13]	Sokolov Viacheslav I.. Synthesis and Application of N-Cyclopalladated Ferrocene Derivatives [J]. Chin. J. Org. Chem., 2018, 38(1): 75-85.
[14]	Qu Renyu, Chen Nian, Liu Yuchao, Chen Qiong, Yang Guangfu. An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation [J]. Chin. J. Org. Chem., 2017, 37(5): 1266-1272.
[15]	Jia Wan, Zhao Lizhi, Wei Hengxu, Zhu Lindong, Fu Lei, Chen Weichun. Iron-Catalyzed Cross-Coupling of Secondary Alkyl Chloride and the Alkynes Grignard Reagent [J]. Chin. J. Org. Chem., 2016, 36(5): 1060-1064.

光/镍协同催化实现C(sp3)—H键选择性官能团化