可见光介导的羰基α位C—H官能团化反应合成萘咪酮类衍生物
收稿日期: 2024-06-30
修回日期: 2024-08-31
网络出版日期: 2024-09-27
基金资助
浙江省科技厅重点研发计划(2024C01203)
Synthesis of Nafimidone Derivatives by Visible-Light-Induced α-C—H Functionalization of Carbonyl
Received date: 2024-06-30
Revised date: 2024-08-31
Online published: 2024-09-27
Supported by
Key Research & Development Project of Science Technology Department of Zhejiang Province(2024C01203)
沈佳斌 , 沈超 , 章鹏飞 . 可见光介导的羰基α位C—H官能团化反应合成萘咪酮类衍生物[J]. 有机化学, 2025 , 45(2) : 677 -685 . DOI: 10.6023/cjoc202406051
A universal and practical visible-light-induced α-functionalization of carbonyl compounds is demonstrated using Esoin Y as photocatalyst. This mild transformation provides an efficient and convenient approach for the synthesis of potentially bioactive nafimidone derivatives with operational simplicity, a broad substrate scope and high atom economy. The mechanistic studies reveal that a free radical pathway mechanism is responsible for this transformation.
| [1] | Acar, M. F.; Sari, S.; Dalkara, S. Drug Dev. Res. 2019, 80, 606. |
| [2] | ?zdemir, Z.; Sari, S.; Karakurt, A.; Dalkara, S. Drug Dev. Res. 2019, 80, 269. |
| [3] | Sari, S.; Karakurt, A.; Uslu, H.; Kaynak, F. B.; ?al?s, ü.; Dalkara, S. Eur. J. Med. Chem. 2016, 124, 407. |
| [4] | Yamada, K.; Yajima, O.; Yoshizawa, Y.; Oh, K. Bioorg. Med. Chem. 2013, 21, 2451. |
| [5] | Weitz, J. I.; Chan, N. C. Arterioscler., Thromb., Vasc. Biol. 2019, 39, 7. |
| [6] | Lu, X.; He, S.; Li, Q.; Yang, H.; Jiang, X.; Lin, H.; Chen, Y.; Qu, W.; Feng, F.; Bian, Y.; Zhou, Y.; Sun, H. Bioorg. Med. Chem. 2018, 26, 1665. |
| [7] | Macarini, A. F.; Sobrinho, T. U. C.; Rizzi, G. W.; Corrêa, R. Med. Chem. Res. 2019, 28, 1235. |
| [8] | Rilatt, I.; Mirabel, E.; Le Grand, B.; Perez, M. Bioorg. Med. Chem. 2010, 20, 903. |
| [9] | (a) Ouyang, W.-T.; Jiang, J.; Jiang, Y.-F.; Li, T.; Liu, Y.-Y.; Ji, H.-T.; Ou, L.-J.; He, W.-M. Chin. Chem. Lett. 2024, 35, 110038. |
| [9] | (b) Hou, J.-C.; Ji, H.-T.; Lu, Y.-H.; Wang, J.-S.; Xu, Y.-D.; Zeng, Y.-Y.; He, W.-M. Chin. Chem. Lett. 2024, 35, 109514. |
| [9] | (c) Chen, X.; Ouyang, W.-T.; Li, X.; He, W.-M. Chin. J. Org. Chem. 2023, 43, 4213 (in Chinese). |
| [9] | (陈祥, 欧阳文韬, 李潇, 何卫民, 有机化学, 2023, 43, 4213.) |
| [9] | (d) Guo, Y.; Zhu, J.; Wang, Y.; Li, Y.; Hu, H.; Zhang, P.; Xu, J.; Li, W. ACS Catal. 2024, 14, 619. |
| [9] | (e) Zhang, L.; Wang, Y.; Shen, J.; Xu, H.; Shen, C. Org. Chem. Front. 2024, 11, 2727. |
| [9] | (f) Liu, Y.; Pang, Q.; Chen, B.; Zhu, Z.; Shen, J.; Zhang, P. Mol. Catal. 2024, 569, 114592. |
| [9] | (g) Yi, R.-N.; He, W.-M. Chin. Chem. Lett. 2024, 35, 110194. |
| [10] | (a) Li, L.; Pang, Q.; Chen, B.; Liu, Y.; Zhao, Y.; Wu, J.; Ge, K.; Shen, J.; Zhang, P. Org. Lett. 2024, 26, 7060. |
| [10] | (b) Xu, J.; Zhang, Y.; Xu, R.; Wang, Y.; Shen, J.; Li, W. Org. Chem. Front. 2024, 11, 5122. |
| [10] | (c) Shen, J.; Yang, Y.; Chen, C.; Xu, H.; Shen, C.; Zhang, P. Org. Chem. Front. 2024, 11, 1758. |
| [10] | (d) Yi, R.; He, W. Chin. J. Org. Chem. 2024, 44, 1035 (in Chinese). |
| [10] | (易荣楠, 何卫民, 有机化学, 2024, 44, 1035.) |
| [10] | (e) Ma, C.; Luo, H.; Zhang, F.; Guo, D.; Chen, S.; Wang, F. Chin. J. Org. Chem. 2024, 44, 216 (in Chinese). |
| [10] | (马翠云, 罗海澜, 张福华, 郭丹, 陈树兴, 王飞, 有机化学, 2024, 44, 216.) |
| [10] | (f) Xu, J.; Hong, Y.; Xu, R.; Wang, Y.; Guo, Y.; Shen, J.; Zhao, Y.; Li, W. Org. Chem. Front. 2024, 11, 6166. |
| [11] | Tian, H.; Xu, W.; Liu, Y.; Wang, Q. Org. Lett. 2020, 22, 5005. |
| [12] | Wang, J.; Ye, Y.; Sang, T.; Zhou, C.; Bao, X.; Yuan, Y.; Huo, C. Org. Lett. 2022, 24, 7577. |
| [13] | Wang, Y.-L.; Zhang, T.-X.; Zhang, X.-M.; Sun, H.-Y.; Leng, J.-Y.; Li, Y.-M. Chin. J. Org. Chem. 2023, 43, 4284 (in Chinese). |
| [13] | (王永玲, 张铁欣, 张栩铭, 孙晗扬, 冷津瑶, 李亚明, 有机化学, 2023, 43, 4284.) |
| [14] | Shen, J.; Wang, Z.; Zhang, Y.; Xu, J.; Shen, C.; Zhang, P. Org. Chem. Front. 2023, 10, 605. |
| [15] | (a) Wang, Z.; Hu, L.; Zhao, M.; Dai, L.; Hrynsphan, D.; Tatsiana, S.; Chen, J. BioChar 2022, 4, 28. |
| [15] | (b) Lv, S.; Zheng, F.; Wang, Z.; Hayat, K.; Veiga, M. C.; Kennes, C.; Chen, J. Sci. Total Environ. 2024, 908, 168339. |
| [15] | (c) Guo, T.; Yue, H.; Ma, C.; Li, S.; Chen, J.; Li, W.; Zhao, J. Biorem. J. 2022, 26, 171. |
| [15] | (d) Yao, J.; Mei, Y.; Yuan, B.; Zheng, F.; Wang, Z.; Chen, J. Environ. Res. 2024, 241, 117613. |
| [15] | (e) Wang, Z.; Chen, C.; Liu, H.; Hrynshpan, D.; Savitskaya, T.; Chen, J.; Chen, J. Ecotoxicol. Environ. Saf. 2019, 183, 109507. |
| [15] | (f) Wang, Z.; Fu, W.; Hu, L.; Zhao, M.; Guo, T.; Hrynsphan, D.; Tatsiana, S.; Chen, J. Sci. Total Environ. 2021, 781, 146686. |
| [15] | (g) Wang, Z.; Chen, C.; Liu, H.; Hrynshpan, D.; Savitskaya, T.; Chen, J.; Chen, J. Sci. Total Environ. 2020, 708, 135063. |
| [15] | (h) Wang, Z.; Dai, L.; Yao, J.; Guo, T.; Hrynsphan, D.; Tatsiana, S.; Chen, J. Chemosphere 2021, 281, 130718. |
| [16] | Yuan, P.-F.; Zhang, Q.-B.; Jin, X.-L.; Lei, W.-L.; Wu, L.-Z.; Liu, Q. Green Chem. 2018, 20, 5464. |
| [17] | (a) Shen, J.; Wang, Z.; Zhang, Y.; Xu, J.; Liu, X.; Shen, C.; Zhang, P. Org. Lett. 2022, 24, 3614. |
| [17] | (b) Shen, J.; Wang, Z.; Shen, C.; Zhang, P. Mol. Catal. 2023, 537, 112950. |
| [17] | (c) Wang, Z.; Chen, B.; Pang, Q.; Xu, J.; Shen, J.; Xu, J.; Li, W. Mol. Catal. 2024, 559, 114060. |
| [17] | (d) Wang, Z.; Li, J.; Liu, Y.; Chen, Q.; Zhang, P.; Wu, J. Mol. Catal. 2023, 540, 113038. |
| [18] | (a) Shen, J.; Xu, J.; He, L.; Liang, C.; Li, W. Chin. Chem. Lett. 2022, 33, 1227. |
| [18] | (b) Shen, J.; Xu, J.; He, L.; Ouyang, Y.; Huang, L.; Li, W.; Zhu, Q. Zhang, P. Org. Lett. 2021, 23, 1204. |
| [18] | (c) Liang, C.; Wang, Z.; Chen, Q.; Wu, J.; Zhang, P.; Shen, J. Mol. Catal. 2024, 558, 114024. |
| [18] | (d) Li, L.; Liu, Y.; Li, J.; Chen, Q.; Zhang, P.; Shen, J.; Wu, J. Adv. Synth. Catal. 2023, 365, 3112. |
| [18] | (e) Zhu, J.; Hong, Y.; Wang, Y.; Guo, Y.; Zhang, Y.; Ni, Z.; Li, W.; Xu, J. ACS Catal. 2024, 14, 6247. |
/
| 〈 |
|
〉 |