Chinese Journal of Organic Chemistry >
Research Progress in Free Radical Fluorosulfonylation
Received date: 2024-07-04
Revised date: 2024-09-01
Online published: 2024-10-11
Supported by
Scientific Research Foundation of Fuzhou Institute of Technology(FTKY2024035); National Natural Science Foundation of China(22071025)
As a distinctive functional group with remarkable reactivity in organic synthesis, sulfonyl fluoride has demon- strated vast application potential in numerous fields, including drug synthesis, chemical biology and materials science. Nonetheless, owing to the growing demand for environmental sustainability in modern chemical synthesis, traditional methods of sulfonyl fluoride synthesis are under reconsideration. Conversely, free radical fluorosulfonylation has emerged as a vital method of introducing the sulfonyl fluoride group, attributed to its superior efficiency, minimal energy consumption, and eco-friendliness. This article will concentrate on the recent advancements in the reaction of free radical fluorosulfonylation.
Jia Zhao , Qiuyun Gan , Yaofeng Yuan . Research Progress in Free Radical Fluorosulfonylation[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1206 -1222 . DOI: 10.6023/cjoc202407012
| [1] | Dong, J.-J.; Krasnova, L.; Finn, M. G.; Sharpless, K. B. Angew. Chem., Int. Ed. 2014, 53, 9430. |
| [2] | Akamanchi, K.; Bellale, E.; Chaudhari, M. Synthesis 2009, 2009, 3211. |
| [3] | Wray, K. L.; Feldman, E. V. J. Chem. Phys. 1971, 54, 3445. |
| [4] | Kiang, T.; Zare, R. N. J. Chem. Soc., Chem. Commun. 1980, 24, 1228. |
| [5] | Leusen, V.; Wildeman, A. M.; Oldenziel, J. O. H. J. Org. Chem. 1977, 42, 1153. |
| [6] | Frye, L. L.; Sullivan, E. L.; Cusack, K. P. J. Org. Chem. 1992, 57, 697. |
| [7] | Truce, W. E.; Madding, G. D. Tetrahedron Lett. 1966, 7, 3681. |
| [8] | Bashir, R.; Awadi, F.; N. A.; Dusouqui, O. M. E. Can. J. Chem. 2005, 83, 1543. |
| [9] | Horner, L.; G?wecke, S. Chem. Ber. 1961, 94, 1267. |
| [10] | Hyatt, J. A.; White, A. W. Synthesis 1984, 1984, 214. |
| [11] | Giel, M. C.; Smedley, C. J.; Mackie, E. R. R.; Guo, T.-J.; Dong, J.-J.; Soares da Costa, T. P.; Moses, J. E. Angew. Chem., Int. Ed. 2020, 59, 1181. |
| [12] | Liang, D.-D.; Streefkerk, D. E.; Jordaan, D.; Wagemakers, J.; Baggerman, J.; Zuilhof, H. Angew. Chem., Int. Ed. 2020, 59, 7494. |
| [13] | Jones, L. H. ACS Med. Chem. Lett. 2018, 9, 584. |
| [14] | Baggio, C.; Udompholkul, P.; Gambini, P.; Salem, F.; Jossart, J.; Perry, J. J. P.; Pellecchia, M. J. Med. Chem. 2019, 62, 9188. |
| [15] | Galvin, C. J.; Genzer, J. Prog. Polym. Sci. 2012, 37, 871. |
| [16] | Xiao, X.; Zhou, F.; Jiang, J.; Chen, H.-F.; Wang, L.-H.; Chen, D.-Y.; Xu, Q.-F.; Lu, J.-M. Polym. Chem. 2018, 9, 1040. |
| [17] | Durie, K.; Yatvin, J.; Kovaliov, M.; Crane, G. H.; Horn, J.; Averick, S.; Locklin, J. Macromolecules 2018, 51, 297. |
| [18] | Chao, Y.; Krishna, A.; Subramaniam, M.; Liang, D.-D.; Pujari, S. P.; Sue, A. C.-H.; Li, G.; Miloserdov, F. M.; Zuilhof, H. Angew. Chem., Int. Ed. 2022, 61, e202207456. |
| [19] | Wang, M.; Jin, H.-S.; Chen, X.-M.; Lin, B.-P.; Yang, H. Polym. Chem. 2019, 10, 3657. |
| [20] | Wan, H.-B.; Zhou, S.-Y.; Gu, P.-Y.; Zhou, F.; Lyu, D.; Xu, Q.-H.; Wang, A.-N.; Shi, H.-B.; Xu, Q.-F.; Lu, J.-M. Polym. Chem. 2020, 11, 1033. |
| [21] | Baker, B. R.; Hurlbut, J. A. J. Med. Chem. 1969, 12, 221. |
| [22] | Teng, M.-X.; Ficarro, S. B.; Yoon, H. J.; Che, J.-W.; Zhou, J.; Fischer, E. S.; Marto, J. A.; Zhang, T.-H.; Gray, N. S. ACS Med. Chem. Lett. 2020, 11, 1269. |
| [23] | Bashashati, M.; Storr, M.; Nikas, S.; Wood, J.; Godlewski, G.; Liu, J.; Ho, W.; Keenan, C.; Zhang, H.; Alapafuja, S.; Cravatt, B.; Lutz, B.; Mackie, K.; Kunos, G.; Patel, K.; Makriyannis, A.; Davison, J.; Sharkey, K. Br. J. Pharmacol. 2012, 165, 1556. |
| [24] | Kitamura, S.; Zheng, Q.-H.; Woehl, J. L.; Solania, A.; Chen, E.; Dillon, N.; Hull, M. V.; Kotaniguchi, M.; Cappiello, J. R.; Kitamura, S.; Nizet, V.; Sharpless, K. B.; Wolan, D. W. J. Am. Chem. Soc. 2020, 142, 10899. |
| [25] | Bianchi, T. A.; Cate, L. A. J. Org. Chem. 1977, 42, 2031. |
| [26] | Wang, L.; Cornella, J. Angew. Chem., Int. Ed. 2020, 59, 23510. |
| [27] | Wright, S. W.; Hallstrom, K. N. J. Org. Chem. 2006, 71, 1080. |
| [28] | Zhang, L.; Cheng, X.; Zhou, Q.-L. Chin. J. Chem. 2022, 40, 1687. |
| [29] | Laudadio, G.; Bartolomeu, A. Verwijlen, L. M. H. M.; Cao, Y.-R.; de Oliveira, K. T.; No?l, T. J. Am. Chem. Soc. 2019, 141, 11832. |
| [30] | Shavnya, A.; Coffey, S. B.; Hesp, K. D.; Ross, S. C.; Tsai, A. S. Org. Lett. 2016, 18, 5848. |
| [31] | Shavnya, A.; Hesp, K. D.; Tsai, A. S. Adv. Synth. Catal. 2018, 360, 1768. |
| [32] | Liu, Y.-A.; Yu, D.-H.; Guo, Y.; Xiao, J.-C.; Chen, Q.-Y.; Liu, C. Org. Lett. 2020, 22, 2281. |
| [33] | Zhong, T.; Yi, J.; Chen, Z.; Zhuang, Q.-L.; Lu, Y.; Weng, G. J. Chem. Sci. 2021, 7, 9359. |
| [34] | Sarver, P. J.; Bissonnette, N. B.; MacMillan, D. W. C. J. Am. Chem. Soc. 2021, 143, 9737. |
| [35] | Ma, Z.; Liu, Y.; Ma, X.; Hu, X.; Guo, Y.; Chen, Q.; Liu, Y.-C. Org. Chem. Front. 2022, 9, 1115. |
| [36] | Nguyen, V. T.; Haug, G. C.; Nguyen, V. D.; Vuong, N. T. H.; Karki, G. B.; Arman, H. D.; Larionov, O. V. Chem. Sci. 2022, 13, 4170. |
| [37] | McDowell, C. A.; Herring, F. G.; Tait, J. C. J. Chem. Phys. 1975, 63, 3278. |
| [38] | Boyd, R. J.; Gupta, A.; Langler, R. F. Can. J. Chem. 1980, 58, 331. |
| [39] | Li, Z.-J. Chem. Phys. Lett. 1997, 269, 128. |
| [40] | Zeng, X.-Q.; Beckers, H.; Willner, H. J. Am. Chem. Soc. 2013, 135, 2096. |
| [41] | Zhong, T.; Chen, Z.-D.; Yi, J.-T.; L, G.; Weng, J. Chin. Chem. Lett. 2021, 32, 2736. |
| [42] | Lee, C.; Cook, A. J.; Elisabeth, E. J.; Friede, N. C.; Sammis, G. M.; Ball, N. D. ACS Catal. 2021, 11, 6578. |
| [43] | Chelagha, A.; Louvel, D.; Taponard, A.; Berthelon, R.; Tlili, A. Catalysts 2021, 11, 830. |
| [44] | Lou, T. S. B.; Willis, M. C. Nat. Rev. Chem. 2022, 6, 146. |
| [45] | He, F.-S.; Li, Y.-Q.; Wu, J. Org. Chem. Front. 2022, 9, 5299. |
| [46] | Barata-Vallejo, S.; Yerien, D. E.; Postigo, A. Catal. Sci. Technol. 2023, 13, 2597. |
| [47] | Zheng, Y.; Lu, W.-G.; Ma, T.-T.; Huang, S.-L. Org. Chem. Front. 2024, 11, 217. |
| [48] | Lin, L.; Pei, G.-H.; Cao, Z.-Y.; Liao, S.-H. Eur. J. Org. Chem. 2024, e202400279. |
| [49] | Van Dyke Tiers, G. US 2846472, 1956. |
| [50] | Nie, X.-L.; Xu, T.-X.; Song, J.-S.; Devaraj, A.; Zhang, B.-L.; Chen, Y.; Liao, S.-H. Angew. Chem., Int. Ed. 2021, 60, 3956. |
| [51] | Nie, X.-L.; Xu, T.-X.; Hong, Y.-H.; Zhang, H.-H.; Mao, C.-X.; Liao, S.-H. Angew. Chem., Int. Ed. 2021, 60, 22035. |
| [52] | Zhao, X.-Y.; Chen, D.-F.; Zhu, S.-Z.; Luo, J.-Y.; Liao, S.-H.; Zheng, B.-N.; Huang, S.-L. Org. Lett. 2023, 25, 3109. |
| [53] | Shi, S.; Zhao, X.-Y.; Chen, D.-F.; Luo, J.-Y.; Liao, S.-H.; Huang, S.-L. Org. Chem. Front. 2023, 10, 3805. |
| [54] | He, T.-Y.; Liang, C.-Q.; Jiang, P.; Liang, H.; Liao, S.-H.; Huang, S.-L. Org. Lett. 2024, 26, 5577. |
| [55] | Zhang, Y.-Y.; Feng, Q.-Y.; Zheng, Y.; Lu, Y.-J.; Liao, S.-H.; Huang, S.-L. Org. Lett. 2024, 26, 1410. |
| [56] | Cheng, H.-Y.; He, T.-Y.; Chen, D.-F.; Zheng, Y.; Lu, Y.; Liang, H.; Liao, S.-H.; Huang, S.-L. Org. Lett. 2024, 26, 3581. |
| [57] | Chen, D.-F.; Nie, X.-L.; Feng, Q.-Y.; Zhang, Y.-Y.; Wang, Y.-H.; Wang, Q.-Y.; Huang, L.; Huang, S.-L.; Liao, S.-H. Angew. Chem., Int. Ed. 2021, 60, 27271. |
| [58] | Feng, Q.-Y.; Fu, Y.-Y.; Zheng, Y.; Liao, S.-H.; Huang, S.-L. Org. Lett. 2022, 24, 3702. |
| [59] | Feng, Q.-Y.; He, T.-Y.; Qian, S.-C.; Xu, P.; Liao, S.-H.; Huang, S.-L. Nat. Commun. 2023, 14, 8278. |
| [60] | Guo, T.-J.; Meng, G.-Y.; Zhan, X.-J.; Yang, Q.; Ma, T.-C.; Xu, L.; Sharpless, K. B.; Dong, J.-J. Angew. Chem., nt. Ed. 2018, 57, 2605. |
| [61] | Wang, P.; Zhang, H.-H.; Nie, X.-L.; Xu, T.-X.; Liao, S.-H. Nat. Commun. 2022, 13, 3370. |
| [62] | Zhang, W.-G.; Li, H.-Y.; Li, X.-J.; Zou, Z.-L.; Huang, M.-J.; Liu, J.-Y.; Wang, X.-C.; Ni, S.-Y.; Pan, Y.; Wang, Y. Nat. Commun. 2022, 13, 3515. |
| [63] | Wang, P.; Zhang, H.-H.; Zhao, M.-Q.; Ji, S.-S.; Lin, L.; Yang, N.; Nie, X.-L.; Song, J.-S.; Liao, S.-H. Angew. Chem., Int. Ed. 2022, 61, e202207684. |
| [64] | Zhang, H.-H.; Yang, N.; Li, J.; Wang, P.; Li, S.-J.; Xie, L.-L.; Liao, S.-H. Org. Lett. 2022, 24, 8170. |
| [65] | Lin, L.; Wang, P.; Dong, T.; Tsui, G. C.; Liao, S.-H. Org. Lett. 2023, 25, 1088. |
| [66] | Yang, N.; Mao, C.-X.; Zhang, H.-H.; Wang, P.; Li, S.-J.; Xie, L.-L.; Liao, S.-H. Org. Lett. 2023, 25, 4478. |
| [67] | Li, H.-Y.; Huang, M.-J.; Zou, Z.-L.; Wang, Z.; Li, Y.-F.; Sun, C.; Chen, W.-Z.; Pan, Y.; Zhang, W.-G.; Wang, Y. Chem. Sci. 2023, 14, 13893. |
| [68] | Fang, X.; Geng, X.-B.; Wang, P.; Zhang, H.-H.; Liao, S.-H. Synthesis 2024, 56, 1727. |
| [69] | Dong, X.-R.; Jiang, W.-H.; Hua, D.-X.; Wang, X.-H.; Xu, L.; Wu, X.-X. Chem. Sci. 2021, 12, 11762. |
| [70] | Frye, N. L.; Daniliuc, C. G.; Studer, A. Angew. Chem., Int. Ed. 2022, 61, e202115593. |
| [71] | Erchinger, J. E.; Hoogesteger, R.; Laskar, R.; Dutta, S.; Hümpel, C.; Rana, D.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2023, 145, 2364. |
| [72] | Cui, J.-C.; Ke, S.; Zhao, J.; Wu, S.-S.; Luo, W.-C.; Xu, S.-N.; Su, X.-L.; Li, Y. Org. Chem. Front. 2022, 9, 3540. |
| [73] | Xiong, T.; Chen, Q.-L.; Chen, Z.-D.; Lu, G.; Chan, A. S. C.; Weng, J. Chem. Catal. 2023, 3, 100821. |
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