电化学介导的S—N键形成: 次磺酰胺化合物的简洁合成
收稿日期: 2021-01-11
修回日期: 2021-03-04
网络出版日期: 2021-03-22
基金资助
国家自然科学基金(22061003)
Electrochemically Mediated S—N Bond Formation: Synthesis of Sulfenamides
Received date: 2021-01-11
Revised date: 2021-03-04
Online published: 2021-03-22
Supported by
National Natural Science Foundation of China(22061003)
何慕雪 , 程诗砚 , 潘永周 , 唐海涛 , 潘英明 . 电化学介导的S—N键形成: 次磺酰胺化合物的简洁合成[J]. 有机化学, 2021 , 41(6) : 2354 -2360 . DOI: 10.6023/cjoc202101017
A series of sulfenamide compounds are synthesized by electrooxidation of thiophenols and amines. The electrosynthesis reaction does not require metal catalysts and oxidizing reagents, and uses simple devices such as single- chamber electrolyzers and constant current electrolysis. This method featured broad substrate scope, ready availability of starting materials, operational simplicity and environmental friendly, which provides a new strategy for the simple and convenient synthesis of various sulfenamide derivatives.
null | (a) O'Driscoll, M.; Greenhalgh, K.; Young, A.; Turos, E.; Dickey, S.; Lim, D. V. Bioorg. Med. Chem. 2008, 16,7832. |
null | (b) Guarino, V. R.; Karunaratne, V.; Stella, V. J. Bioorg. Med. Chem. Lett. 2007, 17,4910. |
null | (c) Craine, L.; Raban, M. Chem. Rev. 1989, 89,689. |
[1] | Klioze, S. S.; Allen, R. C.; Wilker, J. C.; Woodward, D. L. J. Med. Chem. 1980, 23,677. |
[1] | (a) Davis, F. A.; Friedman, A. J.; Kluger, E. W.; Skibo, E. B.; Fretz, E. R.; Milicia, A. P.; LeMasters, W. C.; Bentley, M. D.; Lacadie, J. A.; Douglass, I. B.. J. Org. Chem. 1977, 42,967. |
[1] | (b) Heimer, N. E.; Field, L. J. Org. Chem. 1970, 35,3012. |
[1] | (a) Laudadio, G.; Barmpoutsis, E.; Schotten, C.; Struik, L.; Govaerts, S.; Browne, D. L.; Noe?l, T.. J. Am. Chem. Soc. 2019, 141,5664. |
[1] | (b) Youseflouei, N.; Alizadeh, S.; Masoudi-Khoram, M.; Nematollahi, D.; Alizadeh, H. Electrochim. Acta 2020, 353,136451. |
[1] | (c) Ryu, S. H.; Ra, J.; Ko, H. M. Asian J. Org. Chem. 2020, 9,933. |
[2] | Lee, C.; Wang, X.; Jang, H. Y. Org. Lett. 2015, 17,1130. |
[3] | Liu, S.; Qi, Z.; Zhang, Z.; Qian, B. Org. Lett. 2019, 21,7722. |
[4] | Dou, Y.; Huang, X.; Wang, H.; Yang, L.; Li, H.; Yuan, B.; Yang, G. Green Chem. 2017, 19,2491. |
[4] | (a) Wiebe, A.; Gieshoff, T.; Möhle, S.; Rodrigo, E.; Zirbes, M.; Waldvogel, S. R. Angew. Chem.,Int. Ed. 2018, 57,5594. |
[4] | (b) Wang, M.-R.; Wu, Y.-Z.; Yao, J.; Deng, L.; Pan, Y.-Y.; Huang, K.-B.; Tang, H.-T. Chin. J. Org. Chem. 2019, 39,3223(in Chinese). |
[4] | (王毛锐, 吴雨峥, 姚健, 邓黎, 潘英明, 黄克斌, 唐海涛, 有机化学, 2019, 39,3223.) |
[5] | (a) Xiong, P.; Xu, H.-C. Acc. Chem. Res. 2019, 52,3339. |
[5] | (b) Yan, M.; Kawamata, Y.; Baran, P. S. Chem. Rev. 2017, 117,13230. |
[5] | (c) Wang, X.-Y.; Zhong, Y.-F.; Mo, Z.-Y.; Wu, S.-H.; Xu, Y.-L.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2021, 363,208. |
[5] | (d) Meng, X.-J.; Zhong, P.-F.; Wang, Y.-M.; Wang, H.-S.; Tang, H.-T.; Pan, Y.-M. Adv. Synth. Catal. 2020, 362,506. |
[5] | (e) Feng, E.-Q.; Hou, Z.-W.; Xu, H.-C. Chin. J. Org. Chem. 2019, 39,1424(in Chinese). |
[5] | (冯恩祺, 侯中伟, 徐海超, 有机化学, 2019, 39,1424.) |
[5] | (f) Yu, M.-M.; Shi, W.-Y.; Lei, A.-W. Sci. Sin. Chim. 2021, 51,188(in Chinese). |
[5] | (余明明, 史文研, 雷爱文, 中国科学: 化学, 2021, 51,188.) |
[5] | (g) Zhong, P.-F.; Lin, H,-M.; Wang, L.-W.; Mo, Z.-Y.; Meng, X.-J.; Tang, H.-T.; Pan, Y.-M. Green Chem. 2020, 22,6334. |
[6] | (a) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52,3309. |
[6] | (b) Jiang, Y.; Xu, K.; Zeng, C.-C. Chem. Rev. 2017, 118,4485. |
[6] | (c) Francke, R.; Little, R. D. Chem. Soc. Rev. 2014, 43,2492. |
[6] | (d) Liu, K.; Tang, S.; Wu, T.; Wang, S.; Zou, M.; Cong, H.; Lei, A. Nat. Commun. 2019, 10,639. |
[6] | (e) He, M.-X.; Mo, Z.-Y.; Wang, Z.-Q.; Cheng, S.-Y.; Xie, R.-R.; Tang, H.-T.; Pan, Y.-M.. Org. Lett. 2020, 22,724. |
[6] | (f) Yang, Q.-L.; Wang, X.-Y.; Weng, X.-J.; Yang, X.; Xu, X.-T.; Tong, X.-F.; Fang, P.; Wu, X.-Y.; Mei, T.-S. Acta Chim. Sinica 2019, 77,866(in Chinese). |
[6] | (杨启亮, 王向阳, 翁信军, 杨祥, 徐学涛, 童晓峰, 方萍, 伍新燕, 梅天胜, 化学学报, 2019, 77,866.) |
[6] | (g) Li, M.-F.; Wang, R.; He, W.-J.; Jiang, B. Chin. J. Org. Chem. 2020, 40,1540(in Chinese). |
[6] | (李梦帆, 王榕, 郝文娟, 姜波, 有机化学, 2020, 40,1540.) |
[6] | (h) Pan, C.; Liu, P.; Wu, A.-G.; Li, M.; Wen, L.-R.; Guo, W.-S.. Chin. J. Org. Chem. 2020, 40,2855(in Chinese). |
[6] | (潘超, 刘鹏, 武安国, 李明, 文丽荣, 郭维斯, 有机化学, 2020, 40,2855.) |
[7] | Tang, S.; Liu, Y.; Li, L.; Ren, X.; Li, J.; Yang, G.; Li, H.; Yuan, B. Org. Biomol. Chem. 2019, 17,1370. |
[7] | Zhong, P.-F.; Lin, H.-M.; Wang, L.-W.; Mo, Z.-Y.; Meng, X.-J.; Tang, H.-T.; Pan. Y.-M. Green Chem. 2020, 22,6334. |
[7] | (a) Wang, P.; Tang, S.; Huang, P.; Lei, A. Angew. Chem., Int. Ed. 2017, 56,3009. |
[7] | (b) Wu, J.; Zhou, Y.; Zhou, Y.; Chiang, C. W.; Lei, A. ACS Catal. 2017, 7,8320. |
[7] | (c) Yang, Y. Z.; Song, R. J.; Li, J. H. Org. Lett. 2019, 21,3228. |
/
〈 |
|
〉 |