Chinese Journal of Organic Chemistry >
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.
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
Jinpeng Zhang , Yuliang Qian , Mengyan Ning , Tongqin Cai , Jingyao Su-Zhang , Quan Yu , Liangce Rong . α-Thiocyanation of Enol Acetates and Sodium Thiocyanate under Electrochemical Conditions[J]. Chinese Journal of Organic Chemistry, 2025 , 45(1) : 189 -195 . DOI: 10.6023/cjoc202410007
| [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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