芳基偶氮砜的芳基化及砜基化研究进展
收稿日期: 2021-07-07
修回日期: 2021-07-29
网络出版日期: 2021-08-10
基金资助
山东省高校青创科技计划(2019KJC021); 2018中国科学院“西部之光”人才培养引进计划资助项目
Recent Advances in Arylations and Sulfonylations of Arylazo Sulfones
Received date: 2021-07-07
Revised date: 2021-07-29
Online published: 2021-08-10
Supported by
Youth Innovation and Technology Project of Higher School in Shandong Province(2019KJC021); 2018 CAS "Light of West China" Program
孟娜 , 刘启顺 , 刘瑞生 , 吕玉芬 , 赵晓辉 , 魏伟 . 芳基偶氮砜的芳基化及砜基化研究进展[J]. 有机化学, 2021 , 41(12) : 4639 -4650 . DOI: 10.6023/cjoc202107022
Aromatic ring- and sulfone-containing compounds are widely used in the fields of synthetic chemistry, medicinal chemistry and material chemistry. Therefore, it is of great significance to develop a simple, green and efficient method to construct aryl and sulfonyl compounds. Arylazo sulfones can be used as arylation or sulfonylation reagents to access aryl and sulfonyl compounds via hemolytic cleavage of C—N and N—S bonds to generate aryl radical and sulfonyl radical. In this review, the recent research progress of arylations and sulfonylations using arylazo sulfones is summarized. The synthetic methods and the related reaction mechanisms are highlighted, and an outlook of this research field is also given.
Key words: arylazo sulfones; photocatalysis; electrocatalytic; arylations; sulfonylations
[1] | (a) Hanson, J. R. Nat. Prod. Rep. 1995, 12, 381. |
[1] | (b) Tietze, L. F.; Raschke, T. Synlett 1995, 597. |
[2] | (a) Shiotani, S.; Kometani, T.; Mitsuhashi, K.; Nozawa, T.; Kurobe, A.; Futsukaichi, O. J. Med. Chem. 1976, 19, 803. |
[2] | (b) Smethurst, P. W. R.; Forrest, W. H.; Hayden, J. Br. J. Anaesth. 1971, 43, 1129. |
[3] | (a) Roll, D. M.; Scheuer, P. J.; Matsumoto, G. K.; Clardy, J. J. Am. Chem. Soc. 1983, 105, 6177. |
[3] | (b) Yano, H.; Nakanishi, S. J. Biol. Chem. 1993, 268, 25846. |
[4] | Yuan, Z. Z.; Dai, Q.; Qiao, L.; Zhao, Y. Y.; Zhang, H. M.; Li, X. F. J. Membr. Sci. 2017, 541, 465. |
[5] | (a) Mack, D. J.; Njardarson, J. T. Angew. Chem., Int. Ed. 2013, 52, 1543. |
[5] | (b) Wang, N. Z.; Saidhareddy, P.; Jiang, X. F. Nat. Prod. Rep. 2020, 37, 246. |
[6] | Yazdanyar, S.; Boer, J.; Ingvarsson, G.; Szepietowski, J. C.; Jemec, G. B. E. Dermatology 2011, 222, 342. |
[7] | Li, P.; Hu, D. Y.; Xie, D. D.; Chen, J. X.; Jin, L. H.; Song, B. A. J. Agric. Food Chem. 2018, 66, 3093. |
[8] | (a) Williams, T. M.; Ciccarone, T. M.; MacTough, S. C.; Rooney, C. S.; Balani, S. K.; Condra, J. H.; Emini, E. A.; Goldman, M. E.; Greenlee, W. J. J. Med. Chem. 1993, 36, 1291. |
[8] | (b) Artico, M.; Silvestri, R.; Massa, S.; Loi, A. G.; Corrias, S.; Piras, G.; Colla, P. L. J. Med. Chem. 1996, 39, 522. |
[9] | Kamigta, N.; Kobayashi, M. Sulfur Rep. 1982, 2, 87. |
[10] | (a) Kice, J. L.; Gabrielsen, R. S. J. Org. Chem. 1970, 35, 1004. |
[10] | (b) Kobayashi, M.; Gotoh, M.; Minato, H. J. Org. Chem. 1975, 40, 140. |
[10] | (c) Evers, M. J.; Christiaens, L. E.; Guillaume, M. R.; Renson, M. J. J. Org. Chem. 1985, 50, 1779. |
[10] | (d) Sapountzis, I.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 897. |
[10] | (e) Qiu, D.; Lian, C.; Mao, J.; Fagnoni, M.; Protti, S. J. Org. Chem. 2020, 85, 12813. |
[11] | (a) Gaikwad, D. S.; Pore, D. M. Synlett 2012, 23, 2631. |
[11] | (b) Wang, L.; Bao, P.; Liu, W.; Liu, S.; Hu, C.; Yue, H.; Yang, D.; Wei, W. Chin. J. Org. Chem. 2018, 38, 3189. (in Chinese) |
[11] | ( 王雷雷, 鲍鹏丽, 刘维伟, 刘思彤, 胡昌松, 岳会兰, 杨道山, 魏伟, 有机化学, 2018, 38, 3189.) |
[12] | (a) Shen, Q. L.; Ogata, T.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 6586. |
[12] | (b) Arockiam, P. B.; Fischmeister, C.; Bruneau, C.; Dixneuf, P. H. Green Chem. 2013, 15, 67. |
[12] | (c) Prades, A.; Poyatos, M.; Peris, E. Adv. Synth. Catal. 2010, 352, 1155. |
[13] | (a) Rao Volla, C. M.; Vogel, P. Angew. Chem., Int. Ed. 2008, 47, 1305. |
[13] | (b) Zeng, X. M.; Ilies, L.; Nakamura, E. J. Am. Chem. Soc. 2011, 133, 17638. |
[14] | (a) Duong, H. A.; Gilligan, R. E.; Cooke, M. L.; Phipps, R. J.; Gaunt, M. J. Angew. Chem., Int. Ed. 2011, 50, 463. |
[14] | (b) Vásquez-Céspedes, S.; Holtkamp, M.; Karst, U.; Glorius, F. Synlett 2017, 28, 2759. |
[15] | (a) Kumar, M. R.; Park, K.; Lee, S. Adv. Synth. Catal. 2010, 352, 3255. |
[15] | (b) Hodgetts, K. J.; Kershaw, M. T. Org. Lett. 2003, 5, 2911. |
[16] | (a) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 2044. |
[16] | (b) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. |
[16] | (c) He, W.-B.; Gao, L.-Q.; Chen, X.-J.; Wu, Z.-L.; Huang, Y.; Cao, Z.; Xu, X.-H.; He, W.-M. Chin. Chem. Lett. 2020, 31, 1895. |
[16] | (d) Liu, Q.; Wang, L.; Yue, H.; Li, J.-S.; Luo, Z.; Wei, W. Green Chem. 2019, 21, 1609. |
[16] | (e) Gan, Z.; Li, G.; Yang, X.; Yan, Q.; Xu, G.; Li, G.; Jiang, Y.-Y.; Yang, D. Sci. China: Chem. 2020, 63, 1652. |
[16] | (f) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148. |
[16] | (g) Liu, R.; Liu, Q.; Meng, H.; Ding, H.; Hao, J.; Ji, Z.; Yue, H.; Wei, W. Org. Chem. Front. 2021, 8, 1970. |
[16] | (h) Ye, H.; Xiao, C.; Lu, L. Chin. J. Org. Chem. 2018, 38, 1897. (in Chinese) |
[16] | ( 叶辉, 肖聪, 陆良秋, 有机化学, 2018, 38, 1897.) |
[17] | Crespi, S.; Protti, S.; Fagnoni, M. J. Org. Chem. 2016, 81, 9612. |
[18] | Dossena, A.; Sampaolesi, S.; Palmieri, A.; Protti, S.; Fagnoni, M. J. Org. Chem. 2017, 82, 10687. |
[19] | Sauer, C.; Liu, Y.; Nisi, A. D.; Protti, S.; Fagnoni, M.; Bandini, M. ChemCatChem 2017, 9, 4456. |
[20] | Malacarne, M.; Protti, S.; Fagnoni, M. Adv. Synth. Catal. 2017, 359, 3826. |
[21] | Onuigbo, L.; Raviola, C.; Fonzo, A. D.; Protti, S.; Fagnoni, M. Eur. J. Org. Chem. 2018, 2018, 5297. |
[22] | Xu, Y. L.; Yang, X. Y.; Fang, H. J. Org. Chem. 2018, 83, 12831. |
[23] | (a) Lawrence, D. S.; Copper, J. E.; Smith, C. D. J. Med. Chem. 2001, 44, 594. |
[23] | (b) Willardsen, J. A.; Dudley, D. A.; Cody, W. L.; Chi, L.; McClanahan, T. B.; Mertz, T. E.; Potoczak, R. E.; Narasimhan, L. S.; Holland, D. R.; Rapundalo, S. T.; Edmunds, J. J. J. Med. Chem. 2004, 47, 4089. |
[23] | (c) Galal, S. A.; Khairat, S. H. M.; Ragab, F. A. F.; Abdelsamie, A. S.; Ali, M. M.; Soliman, S. M.; Mortier, J.; Wolber, G.; El Diwani, H. I. Eur. J. Med. Chem. 2014, 86, 122. |
[24] | (a) Yuan, J.; Zhu, J.; Fu, J.; Yang, L.; Xiao, Y.; Mao, P.; Dua, X.; Qu, L. Org. Chem. Front. 2019, 6, 925. |
[24] | (b) Wei, W.; Wang, L.; Bao, P.; Shao, Y.; Yue, H.; Yang, D.; Yang, X.; Zhao, X.; Wang, H. Org. Lett. 2018, 20, 7125. |
[24] | (d) Meng, N.; Lü, Y.; Liu, Q.; Liu, R.; Zhao, X.; Wei, W. Chin. Chem. Lett. 2021, 32, 258. |
[24] | (e) Bao, P.; Liu, F.; Lü, Y.; Yue, H.; Li, J.-S.; Wei, W. Org. Chem. Front. 2020, 7, 492. |
[24] | (h) Shi, J.; Wei, W. Chin. J. Org. Chem. 2020, 40, 2170. (in Chinese) |
[24] | ( 时建伟, 魏伟, 有机化学, 2020, 40, 2170.) |
[25] | Jung, H. I.; Lee, J. H.; Kim, D. Y. Bull. Korean Chem. Soc. 2018, 39, 1003. |
[26] | Lian, C.; Yue, G. L.; Mao, J. S.; Liu, D. Y.; Ding, Y.; Liu, Z. R.; Qiu, D.; Zhao, X.; Lu, K.; Fagnoni, M.; Protti, S. Org. Lett. 2019, 21, 5187. |
[27] | Qiu, D.; Lian, C.; Mao, J. S.; Ding, Y.; Liu, Z. R.; Wei, L. Y.; Fagnoni, M.; Protti, S. Adv. Synth. Catal. 2019, 361, 5239. |
[28] | Liu, Q. S.; Wang, L. L.; Yue, H. L.; Li, J. S.; Luo, Z. D.; Wei, W. Green Chem. 2019, 21, 1609. |
[29] | (a) Zhang, L.; Niu, C.; Yang, X.; Qin, H.; Yang, J.; Wen, J.; Wang, H. Chin. J. Org. Chem. 2020, 40, 1117. (in Chinese) |
[29] | ( 张龙菲, 牛聪, 杨晓婷, 秦宏云, 杨建静, 文江伟, 王桦, 有机化学, 2020, 40, 1117.) |
[29] | (b) Feng, E.; Hou, Z.; Xu, H. Chin. J. Org. Chem. 2019, 39, 1424. (in Chinese) |
[29] | ( 冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39, 1424.) |
[29] | (c) Li, M.; Wang, R.; Hao, W.; Jiang, B. Chin. J. Org. Chem. 2020, 40, 1540. (in Chinese) |
[29] | ( 李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2019, 39, 1540.) |
[29] | (d) Meng, W.; Xu, K.; Guo, B.; Zeng, C. Chin. J. Org. Chem. 2021, 41, 2621. (in Chinese) |
[29] | ( 孟薇, 徐坤, 郭兵兵, 曾程初, 有机化学, 2021, 41, 2621.) |
[29] | (e) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. |
[29] | (f) Chen, J.-Y.; Zhong, C.-T.; Gui, Q.-W.; Zhou, Y.-M.; Fang, Y.-Y.; Liu, K.-J.; Lin, Y.-W.; Cao, Z.; He, W.-M. Chin. Chem. Lett. 2021, 32, 475. |
[30] | Wang, R. K.; Chen, F. M.; Jiang, L. Q.; Yi, W. B. Adv. Synth. Catal. 2020, 363, 1904. |
[31] | (a) Li, Y.; Wan, J.-P. Chin. J. Org. Chem. 2020, 40, 3889. (in Chinese) |
[31] | ( 李毅, 万结平, 有机化学, 2020, 40, 3889.) |
[31] | (b) Liu, Q.; Lü, Y.; Liu, R.; Zhao, X.; Wang, J.; Wei, W. Chin. Chem. Lett. 2021, 32, 136. |
[31] | (c) Bao, W.-H.; Wang, Z.; Tang, X.; Zhang, Y.-F.; Tan, J.-X.; Zhu, Q.; Cao, Z.; Lin, Y.-W.; He, W.-M. Chin. Chem. Lett. 2019, 30, 2259. |
[31] | (d) Lia, G.-H.; Han, Q.-Q.; Sun, Y.-Y.; Chen, D.-M.; Wang, Z.-L.; Xu, X.-M.; Yu, X.-Y. Chin. Chem. Lett. 2020, 31, 3255. |
[31] | (e) Wang, L.; Zhang, M.; Zhang, Y.; Liu, Q.; Zhao, X.; Li, J.-S.; Luo, Z.; Wei, W. Chin. Chem. Lett. 2020, 31, 67. |
[32] | Wei, W.; Liu, C.; Yang, D.; Wen, J.; You, J.; Suo, Y.; Wang, H. Chem. Commun. 2013, 49, 10239. |
[33] | Liu, Q. S.; Liu, F.; Yue, H. L.; Zhao, X. H.; Li, J. S.; Wei, W. Adv. Synth. Catal. 2019, 361, 5277. |
[34] | Lü, Y. F.; Liu, Q. S.; Liu, F.; Yue, H. L.; Li, J. S.; Wei, W. Tetrahedron Lett. 2020, 61, 151335. |
[35] | Chawla, R.; Jaiswal, S.; Dutta, P. K.; Yadav, L. D. S. Tetrahedron Lett. 2020, 61, 151898. |
[36] | Liu, Q. S.; Lü, Y. F.; Liu, R. S.; Zhao, X. H.; Wang, J. W.; Wei, W. Chin. Chem. Lett. 2021, 32, 136. |
/
〈 |
|
〉 |