Chinese Journal of Organic Chemistry >
C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis
Received date: 2022-08-28
Revised date: 2022-10-13
Online published: 2022-11-08
Supported by
National Natural Science Foundation of China(82003585); National Natural Science Foundation of China(21971224); Technical Innovation Team of Henan Normal University(2022TD03); National College Students’ Innovation and Entrepreneurship Training Program of China(202210476076)
2H-Indazole is a privileged scaffold widely existing in drugs and bioactive molecules. The C—H functionalization of 2H-indazole is the cutting edge in medicinal chemistry and organic chemistry. Compared with traditional synthetic methods, the visible light/electrochemical-promoted synthetic method has mild conditions and is an environmentally friendly synthetic strategy. The C—H functionalization of 2-aryl-2H-indazoles at the C-3 position catalyzed by photochemical/electrochemical strategies in recent years is summarized in terms of catalytic systems, with special emphasis on the corresponding reaction mechanism, which might inspire the further development of new catalytic methods.
Key words: 2H-indazole; functionalization; photocatalysis; electrocatalysis
Danfeng Wang , Jin Wang , Chunhua Ma , Yuqin Jiang , Bing Yu . C-3 Functionalization of 2-Aryl-2H-indazoles under Photo/Electrocatalysis[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4024 -4036 . DOI: 10.6023/cjoc202208039
| [1] | Jones, P.; Altamura, S.; Boueres, J.; Ferrigno, F.; Fonsi, M.; Giomini, C.; Lamartina, S.; Monteagudo, E.; Ontoria, J. M.; Orsale, M. V.; Palumbi, M. C.; Pesci, S.; Roscilli, G.; Scarpelli, R.; Schultz-Fademrecht, C.; Toniatti, C.; Rowley, M. J. Med. Chem. 2009, 52, 7170. |
| [2] | Harris, P. A.; Boloor, A.; Cheung, M.; Kumar, R.; Crosby, R. M.; Davis-Ward, R. G.; Epperly, A. H.; Hinkle, K. W.; Hunter, R. N.; Johnson, J. H.; Knick, V. B.; Laudeman, C. P.; Luttrell, D. K.; Mook, R. A.; Nolte, R. T.; Rudolph, S. K.; Szewczyk, J. R.; Truesdale, A. T.; Veal, J. M.; Wang, L.; Stafford, J. A. J. Med. Chem. 2008, 51, 4632. |
| [3] | Clutterbuck, L. A.; Posada, C. G.; Visintin, C.; Riddall, D. R.; Lancaster, B.; Gane, P. J.; Garthwaite, J.; Selwood, D. L. J. Med. Chem. 2009, 52, 2694. |
| [4] | Knoepfel, T.; Nimsgern, P.; Jacquier, S.; Bourrel, M.; Vangrevelinghe, E.; Glatthar, R.; Behnke, D.; Alper, P. B.; Michellys, P.-Y.; Deane, J.; Junt, T.; Zipfel, G.; Limonta, S.; Hawtin, S.; Andre, C.; Boulay, T.; Loetscher, P.; Faller, M.; Blank, J.; Feifel, R.; Betschart, C. J. Med. Chem. 2020, 63, 8276. |
| [5] | Mammoliti, O.; Jansen, K.; El Bkassiny, S.; Palisse, A.; Triballeau, N.; Bucher, D.; Allart, B.; Jaunet, A.; Tricarico, G.; De Wachter, M.; Menet, C.; Blanc, J.; Letfus, V.; Rup?i?, R.; ?mehil, M.; Poljak, T.; Coornaert, B.; Sonck, K.; Duys, I.; Waeckel, L.; Lecru, L.; Marsais, F.; Jagerschmidt, C.; Auberval, M.; Pujuguet, P.; Oste, L.; Borgonovi, M.; Wakselman, E.; Christophe, T.; Houvenaghel, N.; Jans, M.; Heckmann, B.; Sanière, L.; Brys, R. J. Med. Chem. 2021, 64, 14557. |
| [6] | Harrison, J. R.; Brand, S.; Smith, V.; Robinson, D. A.; Thompson, S.; Smith, A.; Davies, K.; Mok, N.; Torrie, L. S.; Collie, I.; Hallyburton, I.; Norval, S.; Simeons, F. R. C.; Stojanovski, L.; Frearson, J. A.; Brenk, R.; Wyatt, P. G.; Gilbert, I. H.; Read, K. D. J. Med. Chem. 2018, 61, 8374. |
| [7] | Chen, N.; Lei, J.; Wang, Z.; Liu, Y.; Sun, K.; Tang, S. Chin. J. Org. Chem. 2022, 42, 1061. |
| [8] | Wang, X.; Lei, J.; Liu, Y.; Ye, Y.; Li, J.; Sun, K. Org. Chem. Front. 2021, 8, 2079. |
| [9] | Zhang, M.-M.; Qu, B.-L.; Shi, B.; Xiao, W.-J.; Lu, L.-Q. Chem. Soc. Rev. 2022, 51, 4146. |
| [10] | Chen, X. Y.; Zhang, X.; Wan, J.-P. Org. Biomol. Chem. 2022, 20, 2356. |
| [11] | Shen, J.; Zhang, L.; Meng, X. Org. Chem. Front. 2021, 8, 6433. |
| [12] | Liu, Z.-K.; Zhao, Q.-Q.; Gao, Y.; Hou, Y.-X.; Hu, X.-Q. Adv. Synth. Catal. 2021, 363, 411. |
| [13] | Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100. |
| [14] | Yang, G.; Xie, X.; Cheng, M.; Gao, X.; Lin, X.; Li, K.; Cheng, Y.; Liu, Y. Chin. Chem. Lett. 2022, 33, 1483. |
| [15] | Qi, Y.; Gu, X.; Huang, X.; Shen, G.; Yang, B.; He, Q.; Xue, Z.; Du, M.; Shi, L.; Yu, B. Chin. Chem. Lett. 2021, 32, 3544. |
| [16] | Wu, Y.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2020, 31, 2999. |
| [17] | Ma, C.-H.; Ji, Y.; Zhao, J.; He, X.; Zhang, S.-T.; Jiang, Y.-Q.; Yu, B. Chin. J. Catal. 2022, 43, 571. |
| [18] | Ghosh, S.; Mondal, S.; Hajra, A. Adv. Synth. Catal. 2020, 362, 3768. |
| [19] | Ghosh, D.; Ghosh, S.; Ghosh, A.; Pyne, P.; Majumder, S.; Hajra, A. Chem. Commun. 2022, 58, 4435. |
| [20] | Chen, Z.; Xuan, J. Chin. J. Org. Chem. 2022, 42, 923. (in Chinese) |
| [20] | ( 陈泽乐, 宣俊, 有机化学, 2022, 42, 923.) |
| [21] | Jiang, Y.-Q.; Li, J.; Feng, Z.-W.; Xu, G.-Q.; Shi, X.; Ding, Q.-J.; Li, W.; Ma, C.-H.; Yu, B. Adv. Synth. Catal. 2020, 362, 2609. |
| [22] | Wang, P.; Zhao, Q.; Xiao, W.; Chen, J. Green Synth. Catal. 2020, 1, 42. |
| [23] | Qu, C.; Liu, R.; Wang, Z.; Lv, Y.; Yue, H.; Wei, W. Green Chem. 2022, 24, 4915. |
| [24] | Lv, Y.; Bao, P.; Yue, H.; Li, J.-S.; Wei, W. Green Chem. 2019, 21, 6051. |
| [25] | Meng, N.; Lv, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. |
| [26] | Meng, Z.; Feng, C.; Xu, K. Chin. J. Org. Chem. 2021, 41, 2535. (in Chinese) |
| [26] | ( 蒙泽银, 冯承涛, 徐坤, 有机化学, 2021, 41, 2535.) |
| [27] | Li, J.; Zhang, S.; Xu, K. Chin. Chem. Lett. 2021, 32, 2729. |
| [28] | Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. |
| [29] | Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52, 3339. |
| [30] | Singsardar, M.; Dey, A.; Sarkar, R.; Hajra, A. J. Org. Chem. 2018, 83, 12694. |
| [31] | Singsardar, M.; Laru, S.; Mondal, S.; Hajra, A. J. Org. Chem. 2019, 84, 4543. |
| [32] | Murugan, A.; Babu, V. N.; Polu, A.; Sabarinathan, N.; Bakthadoss, M.; Sharada, D. S. J. Org. Chem. 2019, 84, 7796. |
| [33] | Neogi, S.; Ghosh, A. K.; Majhi, K.; Samanta, S.; Kibriya, G.; Hajra, A. Org. Lett. 2020, 22, 5605. |
| [34] | Sun, M.; Li, L.; Wang, L.; Huo, J.; Sun, M.; Li, P. Org. Chem. Front. 2021, 8, 4230. |
| [35] | Vidyacharan, S.; Ramanjaneyulu, B. T.; Jang, S.; Kim, D.-P. ChemSusChem 2019, 12, 2581. |
| [36] | Saritha, R.; Annes, S. B.; Ramesh, S. RSC Adv. 2021, 11, 14079. |
| [37] | Ma, C.; Feng, Z.; Li, J.; Zhang, D.; Li, W.; Jiang, Y.; Yu, B. Org. Chem. Front. 2021, 8, 3286. |
| [38] | Saritha, R.; Annes, S. B.; Perumal, K.; Veerappan, A.; Ramesh, S. ChemistrySelect 2021, 6, 12440. |
| [39] | Ma, C.-H.; Zhao, L.; He, X.; Jiang, Y.-Q.; Yu, B. Org. Chem. Front. 2022, 9, 1445. |
| [40] | Aganda, K. C. C.; Kim, J.; Lee, A. Org. Biomol. Chem. 2019, 17, 9698. |
| [41] | Kim, W.; Kim, H. Y.; Oh, K. Org. Lett. 2020, 22, 6319. |
| [42] | Mahanty, K.; Maiti, D.; De Sarkar, S. J. Org. Chem. 2020, 85, 3699. |
| [43] | Sun, M.; Zhou, Y.; Li, L.; Wang, L.; Ma, Y.; Li, P. Org. Chem. Front. 2021, 8, 754. |
| [44] | Wei, T.; Wang, K.; Yu, Z.; Hou, J.; Xie, Y. Tetrahedron Lett. 2021, 86, 153313. |
| [45] | Lin, S.; Cheng, X.; Hasimujiang, B.; Xu, Z.; Li, F.; Ruan, Z. Org. Biomol. Chem. 2022, 20, 117. |
/
| 〈 |
|
〉 |