醋酸烯醇酯与硫氰酸钠电化学条件下α-硫氰化反应
收稿日期: 2024-10-14
修回日期: 2024-12-12
网络出版日期: 2024-12-27
基金资助
江苏省高校自然科学基础研究计划(18KJA150004); 大学生创新创业训练计划(202410320109Y); 江苏省高校品牌专业及徐州美晗生物科技有限公司资助项目
α-Thiocyanation of Enol Acetates and Sodium Thiocyanate under Electrochemical Conditions
Received date: 2024-10-14
Revised date: 2024-12-12
Online published: 2024-12-27
Supported by
Natural Science Foundation of the Jiangsu Higher Education Institutions of China(18KJA150004); Undergraduate Innovation and Entrepreneurship Training Program(202410320109Y); Brand Major of Universities in Jiangsu Province and Xuzhou Meihan Biotechnology Co., Ltd.
张金鹏 , 钱宇亮 , 宁梦妍 , 蔡童钦 , 苏张竞瑶 , 于泉 , 荣良策 . 醋酸烯醇酯与硫氰酸钠电化学条件下α-硫氰化反应[J]. 有机化学, 2025 , 45(1) : 189 -195 . DOI: 10.6023/cjoc202410007
An efficient electrochemical α-thiocyanation of enol acetates and sodium thiocyanate was reported in this research. The results showed that enol acetates derived from different types of ketones could be well used in this reaction strategy, and sodium thiocyanate was an excellent thiocyanate source reagent. This approach has the advantages of simple operation, mild reaction conditions and wide range of substrates, which provides an effective process for obtaining α-thiocyanatoones derivatives.
Key words: electrochemistry; enol acetates; α-thiocyanation; sodium thiocyanate
| [1] | Sun, C.-L., Wang, Y.; Zhou, X.; Wu, Z.-H.; Li, B.-J.; Guan, B.-T.; Shi, Z. J. Chem. Eur. J. 2010, 16, 5844. |
| [2] | Zhang, M.; Zhang, H.-J.; Han, T.; Ruan, W.; Wen, T.-B. J. Org. Chem. 2015, 80, 620. |
| [3] | (a) Chu, H.; Sun, S.; Yu, J.-T.; Cheng, J. Chem. Commun. 2015, 51, 13327. |
| [3] | (b) Zhong, M.; Sun, S.; Cheng, J.; Shao, Y. J. Org. Chem. 2016, 81, 10825. |
| [4] | (a) Vil’, V. A.; Merkulova, V. M.; IIovaisky, A. I.; Paveliev, S. A.; Nikishin, G. I.; Terent’ev, A. O. Org. Lett. 2021, 23, 5107. |
| [4] | (b) Hokamp, T.; Wirth, T. Chem. Eur. J. 2020, 26, 14047. |
| [5] | Mehta, R. G.; Liu, J.; Constantinou, A.; Thomas, C. F.; Hawthorne, M.; You, M.; Gerhäuser, C.; Pezzuto, J. M.; Moon, R. C.; Moriarty, R. M. Carcinogenesis 1995, 16, 399. |
| [6] | Yasman |
| [7] | Wei, Z.-L.; Kozikowski, A. P. J. Org. Chem. 2003, 68, 9116. |
| [8] | Lu, X.; Wang, H.; Gao, R.; Sun, D.; Bi, X. RSC Adv. 2014, 4, 28794. |
| [9] | Renard, P.-Y.; Schwebel, H.; Vayron, P.; Josien, L.; Valleix, A.; Mioskowski, C. Chem. Eur. J. 2002, 8, 2910. |
| [10] | Gonda, J.; Martinková, M.; Raschmanová, J.; Balentová, E. Tetrahedron: Asymmetry 2006, 17, 1875. |
| [11] | Bayarmagnai, B.; Matheis, C.; Jouvin, K.; Goossen, L. J. Angew. Chem., Int. Ed. 2015, 54, 5753. |
| [12] | Zhen, L.; Yuan, K. Li, X.-Y.; Zhang, C.; Yang, J.; Fan, H.; Jiang, L. Org. Lett. 2018, 20, 3109. |
| [13] | See, J. Y.; Zhao, Y. Org. Lett. 2018, 20, 7433. |
| [14] | Ye, A.-H.; Zhang, Y.; Xie, Y.-Y.; Luo, H.-Y.; Dong, J.-W.; Liu, X.-D.; Song, X.-F.; Ding, T.; Chen, Z.-M. Org. Lett. 2019, 21, 5106. |
| [15] | Wang, Z.-L.; Chen, J.; He, Y.-H.; Guan, Z. J. Org. Chem. 2021, 86, 3741. |
| [16] | Chen, W.; Li, T.; Peng, X. New J. Chem. 2021, 45, 14058. |
| [17] | (a) Qian, P.; Jiang, S.; Zhang, W.; Zhang, H.; Ma, Y.; Li, N.; Sheng, L. Adv. Synth. Catal. 2023, 365, 1782. |
| [17] | (b) Zhang, P.; Ma, J.; Liu, X.; Xue, F.; Zhang, Y.; Wang, B.; Jin, W.; Xia, Y.; Liu, C. J. Org. Chem. 2023, 88, 16122. |
| [17] | (c) Taniguchi, N. Synlett 2023, 34, 73. |
| [17] | (d) Wang, Y.; Liu, J.; Wang, Y.; Du, X.; Song, H.; Fang, L.; Wu, L.; Zhang, T. J. Org. Chem. 2024, 89, 3453. |
| [18] | (a) Zhang, Z.; Guo, Y.; Yang, J.; Wu, D.; Wang, J.; Hong, X.; Cai, P.; Rong, L. C. Chin. J. Org. Chem. 2023, 43, 2104 (in Chinese). |
| [18] | (张周, 郭钰, 羊静, 吴丹, 王佳昕, 洪欣玥, 菜佩君, 荣良策, 有机化学, 2023, 43, 2104.) |
| [18] | (b) Wu, Y.; Chen, J.-Y.; Ning, J.; Jiang, X.; Deng, J.; Deng, Y.; Xu, R.; He, W.-M. Green Chem. 2021, 23, 3950. |
| [18] | (c) He, W.-B.; Zhao, S.-J.; Chen, J.-Y.; Jiang, J.; Chen, X.; Xu, X.; He, W.-M. Chin. Chem. Lett. 2023, 34, 107640. |
| [19] | (a) Yuan, Y.; Lei, A. Acc. Chem. Res. 2019, 52, 3309. |
| [19] | (b) Liu, K.; Lei, A. Org. Biomol. Chem. 2018, 16, 2375. |
| [19] | (c) Tang, S.; Zeng, L.; Lei, A. J. Am. Chem. Soc. 2018, 140, 13128. |
| [19] | (d) Yang, Z.; Shi, W.; Alhumade, H.; Yi, H.; Lei, A. Nat. Synth. 2023, 2, 217. |
| [20] | (a) Wang, Y.-Z.; Sun, B.; Zhu, X.-Y.; Gu, Y.-C.; Mei, T.-S. J. Am. Chem. Soc. 2023, 145, 23910. |
| [20] | (b) Liu, Z.-R.; Zhu, X.-Y.; Guo, J.-F.; Ma, C.; Zuo, Z.-W.; Mei, T.-S. Sci. Bull. 2024, 69, 1866. |
| [20] | (c) He, Z.; Liu, H.-L.; Wang, Z.-H.; Jiao, K.-J.; Li, Z.-M.; Li, Z.-J.; Fang, P.; Mei, T.-S. J. Org. Chem. 2023, 88, 6203. |
| [21] | (a) Li, M.; Cheng, X. Nat. Commun. 2024, 15, 7540. |
| [21] | (b) Liu, F.; Ding, W.; Lin, J.; Cheng, X. Org. Lett. 2023, 25, 7617. |
| [21] | (c) Sheng, J.; Cheng, X. CCS Chem. 2024, 6, 230. |
| [22] | (a) Guo, Q.; Jiang, Y.; Zhu, R.; Yang, W.; Hu, P. Angew. Chem., nt. Ed. 2024, 63, e202402878. |
| [22] | (b) Ji, H.-T.; Jiang, J.; He, W.-B.; Lu, Y.-H.; Liu, Y.-Y.; Li, X.; He, W.-M. J. Org. Chem. 2024, 89, 4113. |
| [22] | (c) Zhang, Q.; Liang, K.; Guo, C. Angew. Chem., nt. Ed. 2022, 61, e202210632. |
| [22] | (d) Xiong, P.; Xu, H.-H.; Song, J.; Xu, H.-C. J. Am. Chem. Soc. 2018, 140, 72460. |
| [23] | (a) Dai, L.; Yu, Q.; Zhang, J.; Wu, F.; Wang, C.; Zhang, J. P.; Rong, L. C. J. Org. Chem. 2021, 86, 10568. |
| [23] | (b) Liu, J. Y.; Qian, Y. L.; Zhao, H. C.; Liu, Y.; Qin, Z. L.; Zhang, Z. F.; Rong, L. C. J. Org. Chem. 2024, 89, 15914. |
| [23] | (c) Wu, F.; Guo, Y.; Ren, Z.; Chen, Z.; Liu, X. Q.; Wang, C.; Rong, L. C. J. Org. Chem. 2023, 88, 8825. |
| [23] | (d) Wu, F.; Liu, S. J.; Lv, X. Q.; Pan, M.; Liu, X. Q.; Zhang, J. P.; Rong, L. C. J. Org. Chem. 2023, 88, 13749. |
| [24] | Gong, K.; Ma, Y.; Yu, P.; Gao, S.; Li, Y.; Liang, D.; Sun, S.; Wang, B. Adv. Synth. Catal. 2024, 366, 2352. |
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