Chinese Journal of Organic Chemistry >
Progress in Fluoroalkylation of Multicomponent
Received date: 2020-07-08
Revised date: 2020-08-09
Online published: 2020-09-16
Supported by
National Natural Science Foundation of China(21672151); National Natural Science Foundation of China(21602136)
Multi-component fluoroalkylation is a hot topic in organic fluorine chemistry. In the past few years, due to the development of new reagents and new methods, multi-component fluoroalkylation reactions have made great progress. It can not only introduce fluoroalkyl groups with other functional groups in one step economically and effectively, but also transform the starting materials into a variety of compounds with biological or pharmaceutical. The development of multi-component fluoroalkylation over the past decade is reviewed from seven parts: three-component difluoroalkylation reaction, three-component trifluoroalkylation reaction, three-component perfluoroalkylation reaction, three-component monofluoro- alkylation reaction, three-component fluorination and four-component fluoroalkylation and conclusion. At the same time, this kind of reaction is summarized and prospected.
Jun Pan , Jingjing Wu , Fanhong Wu . Progress in Fluoroalkylation of Multicomponent[J]. Chinese Journal of Organic Chemistry, 2021 , 41(3) : 983 -1001 . DOI: 10.6023/cjoc202007025
| [1] | (a) Xu, J.; Liu, X.; Fu, Y. Tetrahedron Lett. 2014, 55, 585. |
| [1] | (b) Wang, G.; He, X.; Dai, J.; Xu, H. Chin. J. Org. Chem. 2014, 34, 837. (in Chinese) |
| [1] | (王光祖, 赫侠平, 戴建军, 许华建, 有机化学, 2014, 34, 837.) |
| [1] | (c) Zhang, J.; Jin, C.; Zhang, Y. Chin. J. Org. Chem. 2014, 34, 662. (in Chinese) |
| [1] | (张霁, 金传飞, 张英俊, 有机化学, 2014, 34, 662.) |
| [1] | (d) Merino, E.; Nevado, C. Chem. Soc. Rev. 2014, 43, 6598. |
| [1] | (e) Chu, L.; Qing, F. L. Acc. Chem. Res. 2014, 47, 1513. |
| [2] | Qing, F. L. Chin. J. Org. Chem. 2012, 32, 815. (in Chinese) |
| [2] | (卿凤翎, 有机化学, 2012, 32, 815.) |
| [3] | (a) Schlosser, M. Angew. Chem.. Int. Ed. 2006, 45, 5432. |
| [3] | (b) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. |
| [3] | (c) Purse, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [3] | (d) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. |
| [3] | (e) Wang, J.; Liu, H. Chin. J. Org. Chem. 2011, 31, 1785. (in Chinese) |
| [3] | (王江, 柳红, 有机化学, 2011, 31, 1785.). |
| [4] | (a) An, L.; Tong, F. F.; Zhang, X. G. Acta Chim. Sinica 2018, 76, 977. (in Chinese) |
| [4] | (安伦, 童非非, 张新刚, 化学学报, 2018, 76, 977.) |
| [4] | (b) He, X.; Gao, X.; Zhang, X. G. Chin. J. Chem. 2018, 36, 1059. |
| [4] | (c) Xie, Q. Q.; Hu, J. B. Chin. J. Chem. 2020, 38, 202. |
| [5] | (a) Ni, C. F.; Zhu, L. G.; Hu, J. B. Acta Chim. Sinica 2015, 73, 90. (in Chinese) |
| [5] | (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.) |
| [5] | (b) Lü, C. P.; Shen, Q. L.; Liu, D. Chin. J. Org. Chem. 2012, 32, 1380. (in Chinese) |
| [5] | (吕翠萍, 沈其龙, 刘丹, 有机化学, 2012, 32, 1380.). |
| [6] | (a) Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626. |
| [6] | (b) Narjes, F.; Koehler, K. F.; Koch, U.; Gerlach, B.; Colarusso, S.; Steinku?hler, C.; Brunetti, M.; Altamura, S.; De Francesco, R.; Matassa, V. G. Chem. Lett. 2002, 12, 701. |
| [6] | (c) Xu, Y.; Qian, L.; Pontsler, A. V.; McIntyre, T. M.; Prestwich, G. D. Tetrahedron Lett. 2004, 60, 43. |
| [6] | (d) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. |
| [6] | (e) Chowdhury, M. A.; Abdellatif, K. R. A.; Dong, Y.; Das, D.; Suresh, M. R.; Knaus, E. E. J. Med. Chem. 2009, 52, 1525. |
| [7] | (a) Nguyen, J. D.; Tucker, J. W.; Stephenson, C. R. J. J. Am. Chem. Soc. 2011, 133, 4160. |
| [7] | (b) Wallentin, C. J.; Nguyenand, J. D. C.; Stephenson, R. J. J. Am. Chem. Soc. 2012, 134, 8875. |
| [8] | Arai, Y.; Tomita, R.; Ando, G.; Koike, T.; Akita, M. Chem.-Eur. J. 2016, 22, 1262. |
| [9] | Lv, X. L.; Wang, C.; Wang, Q. L.; Shu, W. Org. Lett. 2019, 21, 56. |
| [10] | Xu, R.; Cai, C. Chem. Commun. 2019, 55, 4383. |
| [11] | Shu, W.; Merino, E.; Nevado, C. ACS Catal. 2018, 8, 6401. |
| [12] | Deng, X. Y.; Lin, J. H.; Zheng, J.; Xiao, J. C. Chem. Commun. 2015, 51, 8805. |
| [13] | Zhang, M.; Lin, J. H.; Xiao, J. C. Angew. Chem., Int. Ed. 2019, 58, 6079. |
| [14] | Gu, J. W.; Min, Q. Q.; Yu, L. C.; Zhang, X. Angew. Chem., Int. Ed. 2016, 55, 12270. |
| [15] | Xu, C.; Yang, Z. F.; An, L.; Zhang, X. G. ACS Catal. 2019, 9, 8224. |
| [16] | Zhang, K. F.; Bian, K. J.; Li, C.; Sheng, J.; Li, Y.; Wang, X. S. Angew. Chem., Int. Ed. 2019, 58, 5069. |
| [17] | (a) Bunescu, A.; Wang, Q.; Zhu, J. Angew. Chem.. Int. Ed. 2015, 54, 3132. |
| [17] | (b) Ha, T. M.; Chatalova-Sazepin, C.; Wang, Q.; Zhu, J. Angew. Chem.. Int. Ed. 2016, 55, 9249. |
| [17] | (c) Fan, J.-H.; Wei, W. T.; Zhou, M. B.; Song, R. J.; Li, J. H. Angew. Chem.. Int. Ed. 2014, 53, 6650. |
| [17] | (d) Ouyang, X. H.; Song, R. J.; Hu, M.; Yang, Y.; Li, J. H. Angew. Chem.. Int. Ed. 2016, 55, 3187. |
| [17] | (e) Liu, Y. Y.; Yang, X. H.; Song, R. J.; Luo, S.; Li, J. H. Nat. Commun. 2017, 8, 14720. |
| [17] | (f) Zhou, S. F.; Li, D. P.; Liu, K.; Zou, J. P.; Asekun, O. T. J. Org. Chem. 2015, 80, 1214. |
| [18] | Kong, W.; Yu, C.; An, H.; Song, Q. L. Org. Lett. 2018, 20, 4975. |
| [19] | (a) Ke, M.; Feng, Q.; Yang, K.; Song, Q. L. Org. Chem. Front. 2016, 3, 150. |
| [19] | (b) Ke, M.; Song, Q. J. Org. Chem. 2016, 81, 3654. |
| [19] | (c) Ke, M.; Song, Q. Adv. Synth. Catal. 2017, 359, 384. |
| [19] | (d) Ke, M.; Song, Q. Chem. Commun. 2017, 53, 2222. |
| [19] | (e) Fu, W.; Song, Q. Org. Lett. 2018, 20, 393. |
| [20] | Chen, Y. J.; Li, L. K.; Ma, Y. Y.; Li, Z. P. J. Org. Chem. 2019, 84, 5328. |
| [21] | He, Y. T.; Wang, Q.; Li, L. H.; Liu, X. Y.; Xu, P. F.; Liang, Y. M. Org. Lett. 2015, 17, 5188. |
| [22] | He, Y. T.; Li, L. H.; Wang, Q.; Wu, W.; Liang, Y. M. Org. Lett. 2016, 18, 5158. |
| [23] | Zhang, P. B.; Ying, J. X.; Tang, G.; Zhao, Y. F. Org. Chem. Front. 2017, 4, 2054. |
| [24] | Liang, J.Q; Huang, G. Z.; Peng, P.; Zhang, T.; Wu, J.; Wu, F. Adv. Synth. Catal. 2018, 360, 2221. |
| [25] | (a) Suginome, M.; Yamamoto, A.; Murakami, M. J. Am. Chem. Soc. 2003, 125, 6358. |
| [25] | (b) Suginome, M.; Yamamoto, A.; Murakami, M. Angew. Chem.. Int. Ed. 2005, 44, 2380. |
| [25] | (c) Suginome, M.; Shirakura, M.; Yamamoto, A. J. Am. Chem. Soc. 2006, 128, 14438. |
| [26] | (a) Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2005, 127, 15706. |
| [26] | (b) Daini, M.; Yamamoto, A.; Suginome, M. J. Am. Chem. Soc. 2008, 130, 2918. |
| [26] | (c) Zhang, L.; Cheng, J.; Carry, B.; Hou, Z. J. Am. Chem. Soc. 2012, 134, 14314. |
| [26] | (d) Alfaro, R.; Parra, A.; Alema?n, J.; Ruano, J. L. G.; Tortosa, M. J. Am. Chem. Soc. 2012, 134, 15165. |
| [26] | (e) Yoshida, H.; Kageyuki, I.; Takaki, K. Org. Lett. 2013, 15, 952. |
| [26] | (f) Zhou, Y.; You, W.; Smith, K. B.; Brown, M. K. Angew. Chem.. Int. Ed. 2014, 53, 3475. |
| [26] | (g) Bidal, Y. D.; Lazreg, F.; Cazin, C. S. J. Am. Chem. Soc. 2014, 4, 1564. |
| [26] | (h) Nakagawa, N.; Hatakeyama, T.; Nakamura, M. Chem.-Eur. J. 2015, 21, 4257. |
| [26] | (i) Bin, H. Y.; Wei, X.; Zi, J.; Zuo, Y. J.; Wang, T. C.; Zhong, C. M. ACS Catal. 2015, 5, 6670. |
| [26] | (j) Kubota, K.; Iwamoto, H.; Yamamoto, E.; Ito, H. Org. Lett. 2015, 17, 620. |
| [26] | (k) Su, W.; Gong, T. J.; Zhang, Q.; Zhang, Q.; Xiao, B.; Fu, Y. ACS Catal. 2016, 6, 6417. |
| [26] | (l) Itoh, T.; Shimizu, Y.; Kanai, M. J. Am. Chem. Soc. 2016, 138, 7528. |
| [26] | (m) Mateos, J.; Rivera-Chao, E.; Fan?ana?s-Mastral, M. ACS Catal. 2017, 7, 5340. |
| [26] | (n) Han, J. T.; Yun, J. Org. Lett. 2018, 20, 2104. |
| [27] | (a) Mannathan, S.; Jeganmohan, M.; Cheng, C. H. Angew. Chem.. Int. Ed. 2009, 48, 2192. |
| [27] | (b) Okuno, Y.; Yamashita, M.; Nozaki, K. Angew. Chem.. Int. Ed. 2011, 50, 920. |
| [27] | (c) Nagao, K.; Ohmiya, H.; Sawamura, M. J. Am. Chem. Soc. 2014, 136, 10605. |
| [27] | (d) Yamazaki, A.; Nagao, K.; Lwai, T.; Ohmiya, H.; Sawamura, M. Angew. Chem.. Int. Ed. 2018, 57, 3196. |
| [27] | (e) Roscales, S.; Csa?ky?, A. G. Org. Lett. 2015, 17, 1605. |
| [27] | (f) Nogami, M.; Hirano, K.; Kanai, M.; Wang, C.; Saito, T.; Miyamoto, K.; Muranaka, A.; Uchiyama, M. J. Am. Chem. Soc. 2017, 139, 12358. |
| [28] | Wang, S. F.; Zhang, J.; Kong, L. C.; Tan, Z.; Bai, Y. H.; Zhu, G. G. Org. Lett. 2018, 20, 5631. |
| [29] | Guo, W. H.; Zhao, H. Y.; Luo, Z. J.; Zhang, S.; Zhang, X. G. ACS Catal. 2019, 9, 38. |
| [30] | Yasu, Y.; Koike, T.; Akita, M. Angew. Chem., Int. Ed. 2012, 51, 9567. |
| [31] | Li, Y.; Studer, A. Angew. Chem., Int. Ed. 2012, 51, 8221. |
| [32] | Feng, C.; Loh, T.-P. Chem. Sci. 2012, 3, 3458. |
| [33] | Carboni, A.; Dagousset, G.; Magnier, E.; Masson, G. Org. Lett. 2014, 16, 1240. |
| [34] | (a) Sani, M.; Bruche?, L.; Chiva, G.; Fustero, S.; Piera, J.; Volonterio, A.; Zanda, M. Angew. Chem.. Int. Ed. 2003, 42, 2060. |
| [34] | (b) Ogu, K.; Matsumoto, S.; Akazome, M.; Ogura, K. Org. Lett. 2005, 7, 589. |
| [34] | (c) Jakowiecki, J.; Loska, R.; Makosza, M. J. Org. Chem. 2008, 73, 5436. |
| [34] | (d) Fustero, S.; Chiva, G.; Piera, J.; Sanz-Cervera, J. F.; Volonterio, A.; Zanda, M.; Ramirez de Arellano, C. J. Org. Chem. 2009, 74, 3122. |
| [34] | (e) Benhaim, C.; Bouchard, L.; Pelletier, G.; Sellstedt, J.; Kristofova, L.; Daigneault, S. Org. Lett. 2010, 12, 2008. |
| [35] | Huang, L.; Zheng, S. C.; Tan, B.; Liu, X. Y. Org. Lett. 2015, 17, 1589. |
| [36] | (a) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1991, 32, 7525. |
| [36] | (b) Langlois, B. R.; Laurent, E.; Roidot, N. Tetrahedron Lett. 1992, 33, 1291. |
| [37] | Yang, Y. D.; Iwamoto, K.; Tokunaga, E.; Shibata, N. Chem. Commun. 2013, 49, 5510. |
| [38] | Ji, Y.; Brueckl, T.; Baxter, R. D.; Seiple, I. B.; Su, S.; Blackmond, D. G.; Baran, P. S. Proc. Natl. Acad. Sci. U.S. A. 2011, 108, 14411. |
| [39] | Ye, Y.; Kunzi, S.; Sanford, M. S. Org. Lett. 2012, 14, 4979. |
| [40] | Jiang, X. Y.; Qing, F. L. Angew. Chem., Int. Ed. 2013, 52, 14177. |
| [41] | Wang, F.; Qi, X.; Liang, Z.; Chen, P.; Liu, G. S. Angew. Chem., Int. Ed. 2014, 53, 1881. |
| [42] | Dagousset, G.; Carboni, A.; Magnier, E.; Masson, G. Org. Lett. 2014, 16, 4340. |
| [43] | Yang, X.; Sun, Y. W.; Zhang, G. Z. Org. Lett. 2018, 20, 6250. |
| [44] | Li, Q.; Wang, W.; Berst, K. B.; Claiborne, A.; Hasvold, L.; Raye, K. M.; Nilius, T. A.; Shen, L. L.; Flamm, R.; Alder, J.; Marsh, K.; Crowell, D.; Chu, D. T. W.; Plattner, J. J. Bioorg. Med. Chem. Lett. 1998, 8, 1953. |
| [45] | Zhu, C. L.; Wang, C.; Qin, Q. X.; Yruegas, S.; Martin, C. D.; Xu, H. ACS Catal. 2018, 8, 12317. |
| [46] | Liang, Z.; Wang, F.; Chen, P.; Liu, G. Org. Lett. 2015, 17, 2438. |
| [47] | Grishchuk, B. D.; Prodanchuk, N. G.; Sinchenko, V. G.; Gorbovoi, P. M.; Kudrik, E. Y. Pharm. Chem. J. 1994, 28, 657. |
| [48] | Szajnman, S. H.; Yan, W.; Bailey, B. N.; Docampo, R.; Elhalem, E.; Rodriguez, J. B. J. Med. Chem. 2000, 43, 1826. |
| [49] | Kong, W.; An, H.; Song, Q. Chem Commun. 2017, 53, 8968. |
| [50] | (a) Murdoch, D.; Keam, S. Drugs 2005, 65, 2379. |
| [50] | (b) Ozoe, Y.; Ishikawa, S.; Tomiyama, S.; Ozoe, F.; Kozaki, T.; Scott, J. G. J. Am. Chem. Soc. 2007, 948, 39. |
| [51] | He, Y. T.; Li, L. H.; Yang, Y. F.; Zhou, Z. Z.; Hua, H. L.; Liu, X. Y.; Liang, Y. M. Org. Lett. 2014, 16, 270. |
| [52] | Ichenko, N. O.; Janson, P. G.; Szabo?, K. J. J. Org. Chem. 2013, 78, 11087. |
| [53] | Liang, Z.; Wang, F.; Chen, P.; Liu, G. J. Fluorine Chem. 2014, 167, 55. |
| [54] | Wang, F.; Wang, D.; Wan, X.; Wu, L.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2016, 138, 15547. |
| [55] | Zhang, Z. Q.; Meng, X. Y.; Sheng, J.; Lan, Q.; Wang, X. S. Org. Lett. 2019, 21, 8256. |
| [56] | Jarrige, L.; Carboni, A.; Dagousset, G.; Levitre, G.; Magnier, E.; Masson, G. Org. Lett. 2016, 18, 2906. |
| [57] | Mora?n-Ramallal, R.; Gotor-Ferna?ndez, V.; Laborda, P.; Sayago, F. J.; Cativiela, C.; Gotor, V. Org. Lett. 2012, 14, 1696. |
| [58] | Zhu, Y.; Tian, J. L.; Gu, X. F.; Wang, Y. H. J. Org. Chem. 2018, 83, 13267. |
| [59] | (a) Ghera, E.; Shoua, S. Tetrahedron Lett. 1974, 15, 3843. |
| [59] | (b) Zhao, B.; Yuan, W.; Du, H.; Shi, Y. Org. Lett. 2007, 9, 4943. |
| [59] | (c) Taniguchi, T.; Sugiura, Y.; Zaimoku, H.; Ishibashi, H. Angew. Chem.. Int. Ed. 2010, 49, 10154. |
| [59] | (d) Taniguchi, T.; Idota, A.; Yokoyama, S.; Ishibashi, H. Tetrahedron Lett. 2011, 52, 4768. |
| [59] | (e) Taniguchi, T.; Zaimoku, H.; Ishibashi, H. Chem.-Eur. J. 2011, 17, 4307. d7eb27a5-b391-48dd-975b-08dfeeb296cf |
| [59] | (f) Zhang, H.; Song, Y.; Zhao, J.; Zhang, J.; Zhang, Q. Angew. Chem.. Int. Ed. 2014, 53, 11079. |
| [59] | (g) Lu, D. F.; Zhu, C. L.; Jia, Z. X.; Xu, H. J. Am. Chem. Soc. 2014, 136, 13186. |
| [59] | (h) Zhu, R.; Buchwald, S. L. J. Am. Chem. Soc. 2015, 137, 8069. |
| [59] | (i) Sun, X.; Li, X.; Song, S.; Zhu, Y.; Liang, Y. F.; Jiao, N. J. Am. Chem. Soc. 2015, 137, 6059. |
| [59] | (j) Miner, M. R.; Woerpel, K. A. Eur. J. Org. Chem. 2016, 2016, 1860. |
| [59] | (k) Lu, D. F.; Zhu, C. L.; Sears, J. D.; Xu, H. J. Am. Chem. Soc. 2016, 138, 11360. |
| [59] | (l) Cheng, J. K.; Loh, T. P. J. Am. Chem. Soc. 2015, 137, 42. |
| [59] | (m) Andia, A. A.; Miner, M. R.; Woerpel, K. A. Org. Lett. 2015, 17, 2704. |
| [60] | (a) Alameda-Angulo, C.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 2006, 47, 913. |
| [60] | (b) Soueni, A. E.; Tedder, J. M.; Walton, J. C. J. Fluorine Chem. 1981, 17, 51. |
| [60] | (c) Poutsma, M.; Ibarbia, P. J. Org. Chem. 1970, 35, 4038. |
| [61] | Wang, F.; Wang, D. H.; Zhou, Yu.; Liang, L.; Lu, R. H.; Chen, P. H.; Lin, Z. Y.; Liu, G. S. Angew. Chem., Int. Ed. 2018, 57, 7140. |
| [62] | Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202. |
| [63] | Wu, L.; Wang, F.; Wan, X.; Wang, D.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2017, 139, 2904. |
| [64] | Ye, J. H.; Song, L.; Zhou, W. J.; Ju, T.; Yin, Z. B.; Yan, S. S.; Zhang, Z.; Li, J.; Yu, D. G. Angew. Chem., Int. Ed. 2016, 55, 10022. |
| [65] | Zhou, S.; Song, T.; Chen, H.; Liu, Z.; Shen, H.; Li, C. Org. Lett. 2017, 19, 698. |
| [66] | Fu, L.; Zhou, S.; Wan, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2018, 140, 10965. |
| [67] | (a) Fadeyi, O. O.; Adamson, S. T.; Myles, E. L.; Okoro, C. O. Bioorg. Med. Chem. Lett. 2008, 18, 4172. |
| [67] | (b) Li, J.; Zhang, X.; Xiang, H.; Tong, L.; Feng, F.; Xie, H.; Ding, J.; Yang, C. J. Org. Chem. 2017, 82, 6795. |
| [67] | (c) Apraku, J.; Okoro, C. O. Bioorg. Med. Chem. 2019, 27, 161. |
| [68] | Li, J. L.; Liu, Y. Q.; Zou, W. L.; Zeng, R.; Zhang, X.; Liu, Y.; Han, B.; He, Y.; Leng, H. J.; Li, Q. Z. Angew. Chem., Int. Ed. 2020, 59, 1863. |
| [69] | (a) Park, C. M.; Jiang, Y. J. Chem. Sci. 2014, 5, 2347. |
| [69] | (b) Jana, S.; Clements, M. D.; Sharp, B. K.; Zheng, N. Org. Lett. 2010, 12, 3736. |
| [69] | (c) Qi, X. X.; Xu, X. X.; Park, C. M. Chem. Commun. 2012, 48, 3996. |
| [70] | He, Y. T.; Wang, Q.; Zhao, J. H.; Liu, X. Y.; Xua, P. F.; Liang, Y. M. Chem. Commun. 2015, 51, 13209. |
| [71] | (a) Ackermann, L.; Potukuchi, H. K. Org. Biomol. Chem. 2010, 8, 4503. |
| [71] | (b) Spiteri, C.; Moses, J. E. Angew. Chem.. Int. Ed. 2010, 49, 31. |
| [72] | Cheung, K. P. S.; Tsui, G. C. Org. Lett. 2017, 19, 2881. |
| [73] | Zhu, A.; Xing, X. F.; Wang, S. L.; Yuan, D. H.; Zhu, G. M.; Geng, M. W.; Guo, Y. Y.; Zhang, G. S.; Li, L. J. Green Chem. 2019, 21, 3407. |
| [74] | Chen, C.; Xie, Y.; Chu, L.; Wang, R. W.; Zhang, X.; Qing, F. L. Angew. Chem., Int. Ed. 2012, 51, 2492. |
| [75] | Cheng, Y.; Muck-Lichtenfeld, C.; Studer, A. J. Am. Chem. Soc. 2018, 140, 6221. |
| [76] | For reviews of radical additions to C=N bonds: (a) Miyabe, H. Synlett 2012, 23, 1709. |
| [76] | (b) Friestad, G. K. Tetrahedron 2001, 57, 5461. |
| [76] | (c) Friestad, G. K. Eur. J. Org. Chem. 2005, 2005, 3157. |
| [76] | (d) Friestad, G. K.; Mathies, A. K. Tetrahedron 2007, 63, 2541. |
| [76] | (e) Yamada, K.; Tomioka, K. Chem. Rev. 2008, 108, 2874. |
| [77] | Zheng, D. Q.; Studer, A. Org. Lett. 2019, 21, 325. |
| [78] | Zhao, X.; Tu, H. Y.; Guo, L.; Zhu, S. Q.; Qing, F. L.; Chu, L. L. Nat. Commun. 2018, 9, 3488. |
| [79] | Tu, H. Y.; W, F.; Huo, L. P.; Li, Y. B.; Zhu, S. Q.; Zhao, X.; Li, H.; Qing, F. L.; Chu, L. L. J. Am. Chem. Soc. 2020, 142, 9604. |
| [80] | Xiong, H.; Ramkumar, N.; Chiou, M. F.; Jian, W.; Li, Y.; Su, J. H.; Zhang, X.; Bao, H. Nat. Commun. 2019, 10, 1. |
| [81] | Zhu, X. T.; Deng, W. L.; Chiou, M. F.; Ye, C. Q.; Jian, W. J.; Zeng, Y. H.; Jiao, Y. H.; Ge, L.; Li, Y. J.; Zhang, X. H.; Bao, H. L. J. Am. Chem. Soc. 2019, 141, 548. |
| [82] | Chu, X. Q.; Xie, Ting.; Li, Lin.; Ge, D. H.; Shen, Z. L.; Loh, T. P. Org. Lett. 2018, 20, 2749. |
| [83] | (a) Davidson, B. S. Chem. Rev. 1993, 93, 1771. |
| [83] | (b) Jin, Z. Nat. Prod. Rep. 2006, 23, 464. |
| [83] | (c) Scott, J. D.; Williams, R. M. Chem. Rev. 2002, 102, 1669. |
| [84] | (a) Wu, Y. C.; Liron, M.; Zhu, J. J. Am. Chem. Soc. 2008, 130, 7148. |
| [84] | (b) Zhang, C.; Zink, D. L.; Ushio, M.; Burgess, B.; Onishi, R.; Masurekar, P.; Barrett, J. F.; Singh, S. B. Bioorg. Med. Chem. 2008, 16, 8818. |
| [84] | (c) Ii, K.; Ichikawa, S.; Al-Dabbagh, B.; Bouhss, A.; Matsuda, A. J. Med. Chem. 2010, 53, 3793. |
| [84] | (d) Andrade, S. F.; Teixeiraa, C. S.; Ramosb, J. P.; Lopesa, M. S.; Páduaa, R. M.; Oliveiraa, M. C.; Souza-Fagundes, E. M.; Alves, R. J. MedChemComm 2014, 5, 1693. |
| [84] | (e) Andrade, S. F.; Oliveira, B. G.; Pereira, L. C.; Ramos, J. P.; Joaquim, A. R.; Steppe, M. E.; SouzaFagundes, M.; Alves, R. J. Eur. J. Med. Chem. 2017, 138, 13. |
| [85] | Chu, X. Q.; Ge, D. H.; Wang, M. L.; Rao, W. D.; Loh, T. P.; Shen, Z. L. Adv. Synth. Catal. 2019, 361, 4082. |
| [86] | For leading reviews, see: (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. |
| [86] | (b) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850. |
| [87] | For reviews, see: (a) Paria, S.; Reiser, O. ChemCatChem 2014, 6, 2477. |
| [87] | (b) Reiser, O. Acc. Chem. Res. 2016, 49, 1990. |
| [88] | Guo, Q. P.; Wang, M. R.; Wang, Y. F.; Xu, Z. Q.; Wang, R. Chem. Commun. 2017, 53, 12317. |
| [89] | Liu, H.; Guo, Q. P.; Chen, C.; Wang, M. R.; Xu, Z. Q. Org. Chem. Front. 2018, 5, 1522. |
| [90] | Guo, Q. P.; Wang, M. G.; Peng, Q.; Huo, Y. M.; Liu, Q.; Wang, R.; Xu, Z. Q. ACS Catal. 2019, 9, 4470. |
| [91] | Li, Z.; Andre?s, G. D.; Nevado, C. J. Am. Chem. Soc. 2015, 137, 11610. |
| [92] | Li, Z. D.; Merino, E.; Nevado, C. Top. Catal. 2017, 60, 545. |
| [93] | Domański, S.; Cha?adaj, W. ACS Catal. 2016, 6, 3452. |
| [94] | Domanski, S.; Gatlik, B.; Chaladaj, W. Org. Lett. 2019, 21, 5021. |
| [95] | Ni, C. F.; Zhu, L. G.; Hu, J. B. Acta Chim. Sinica 2015, 73, 90. (in Chinese) |
| [95] | (倪传法, 朱林桂, 胡金波, 化学学报, 2015, 73, 90.) |
| [96] | Wu, N. Y.; Xu, X. H.; Qing, F. L. ACS Catal. 2019, 9, 5726. |
| [97] | Zhang, C. W.; Li, Z. D.; Zhu, L.; Yu, L. M.; Wang, Z. T.; Li, C. Z. J. Am. Chem. Soc. 2013, 135, 14082. |
| [98] | Peng, H. H.; Yuan, Z. L.; Wang, H. Y.; Guo, Y. L.; Liu, G. S. Chem. Sci. 2013, 4, 3172. |
| [99] | Yasu, Y.; Koike, T.; Akita, M. Org. Lett. 2013, 15, 2136. |
| [100] | Liu, C. M.; Shi, E.; Xu, F.; Luo, Q.; Wang, H. X.; Chen, J. J.; Wan, X. B. Chem. Commun. 2015, 51, 1214. |
| [101] | Wang, Q.; He, Y. T.; Zhao, J. H.; Qiu, Y. F.; Zheng, L.; Hu, J. Y.; Yang, Y. C.; Liu, X. Y.; Liang, Y. M. Org. Lett. 2016, 18, 2664. |
| [102] | Wang, Q.; Zheng, L.; He, Y. T.; Liang, Y. M. Chem. Commun. 2017, 53, 2814. |
/
| 〈 |
|
〉 |
