Chinese Journal of Organic Chemistry >
Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/ Cyclization for the Synthesis of Oxindoles
Received date: 2022-08-25
Revised date: 2022-09-24
Online published: 2022-10-14
Supported by
National Natural Science Foundation of China(22071211); National Natural Science Foundation of China(21801076); Open Research Fund of School of Chemistry and Chemical Engineering of Henan Normal University(2022C02)
Oxindole derivatives are well developed in many fields, and this special heterocyclic scaffold is more and more widely used in natural products and bioactive molecules due to its unique functionality. Therefore, it is very important to explore new synthesis methods for this motif. A visible light-assisted photocatalyst-free protocol for the efficient synthesis of sulfonylated oxindoles under mild condition was reported. The present method starts from simple and readily available N-arylacrylamide and sodium sulfinates, uses cheap K2S2O8 as oxidant, and features moderate to good yields and excellent functional group tolerance.
Key words: photocatalysis; N-arylacrylamide; oxindole; cyclization; photocatalyst-free
Xiaoting Wu , Feng Zhao , Xiaochen Ji , Huawen Huang . Visible Light-Assisted Photocatalyst-Free Tandem Sulfonylation/ Cyclization for the Synthesis of Oxindoles[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4323 -4331 . DOI: 10.6023/cjoc202208036
| [1] | (a) Cao, Z. Y.; Zhou, F.; Zhou, J. Acc. Chem. Res. 2018, 51, 1443. |
| [1] | (b) Boddy, A. J.; Bull, J. A. Org. Chem. Front. 2021, 8, 1026. |
| [1] | (c) Marchese, A. D.; Larin, E. M.; Mirabi, B.; Lautens, M. Acc. Chem. Res. 2020, 53, 1605. |
| [1] | (d) Sch?nhaber, J.; Müller, T. J. J. Org. Biomol. Chem. 2011, 9, 6196. |
| [1] | (e) So, C. M.; Kwong, F. Y. Chem. Soc. Rev. 2011, 40, 4963. |
| [1] | (f) Galliford, C. V.; Scheidt, K. A. Angew. Chem. Int. Ed. 2007, 46, 8748. |
| [1] | (g) Zhou, F.; Liu, Y. L.; Zhou, J. Adv. Synth. Catal. 2010, 352, 1381. |
| [1] | (h) Deng, Z.; Jin, L.; Wu, Y.; Zhao, X.; RSC Adv. 2017, 7, 30984. |
| [2] | (a) Wang, C.; Liu, L.; Org. Chem. Front. 2021, 8, 1454. |
| [2] | (b) Li, C. C.; Yang, S. D. Org. Biomol. Chem. 2016, 14, 4365. |
| [2] | (c) Tang, S.; Zhou, D.; Deng, Y.; Li, Z.; Yang, Y.; He, J.; Wang, Y. Sci. China Chem. 2015, 58, 684. |
| [2] | (d) Tang, S.; Zhou, D.; Li, Z. H.; Fu, M. J.; Jie, L.; Sheng, R. L.; Li, S. H. Synthesis 2015, 47, 1567. |
| [2] | (e) Tang, S.; Zhou, D.; Wang, Y. C. Eur. J. Org. Chem. 2014, 3656. |
| [2] | (f) Fan, J. H.; Wei, W. T.; Zhou, M. B.; Song, R. J.; Li, J. H. Angew. Chem. Int. Ed. 2014, 126, 6768. |
| [2] | (g) Tang, S.; Zhou, D.; Deng, Y.; Li, Z.; Yang, Y.; He, J.; Wang, Y. Sci. China Chem. 2015, 58, 684. |
| [3] | (a) Xuan, J.; Studer, A. Chem. Soc. Rev. 2017, 46, 4329. |
| [3] | (b) Jiang, J.; Wang, Z.; He, W. M. Chem. Asian J. 2021, 32, 1591. |
| [3] | (c) Li, Y.; Pan, G. A.; Luo, M. J.; Li, J. H. Chem. Commun. 2020, 56, 6907. |
| [3] | (d) Li, J.; Lu, W.; Lu, Y.; Zha, Z.; Wang, Z. Chin. J. Chem. 2022, 40, 195. |
| [4] | (a) Wang, X.; Lei, J.; Liu, Y.; Ye, Y.; Li, J.; Sun, K. Org. Chem. Front. 2021, 8, 2079. |
| [4] | (b) Yuan, L.; Jiang, S. M.; Li, Z. Z.; Zhu, Y.; Yu, J.; Li, L.; Li, M. Z.; Tan, S.; Sheng, R. R. Org. Biomol. Chem. 2018, 16, 2406. |
| [4] | (c) Chen, J.; Cai, Y.; Zhao, G. Adv. Synth. Catal. 2014, 356, 359. |
| [4] | (d) He, Z. Y.; Guo, J. Y.; Tian, S. K. Adv. Synth. Catal. 2018, 360, 1544. |
| [4] | (e) Fan, J. H.; Wei, W. T.; Zhou, M. B.; Song, R. J.; Li, J. H. Angew. Chem. Int. Ed. 2014, 126, 6768. |
| [4] | (f) Yin, F.; Wang, X. S. Org. Lett. 2014, 16, 1128-1131. |
| [4] | (g) Wang, H.; Guo, L. N.; Duan, X. H. J. Org. Chem. 2016, 81, 860. |
| [5] | (a) Li, Y. M.; Sun, M.; Wang, H. L.; Tian, Q. P.; Yang, S. D. Angew. Chem. Int. Ed. 2013, 52, 3972. |
| [5] | (b) Wei, W. T.; Zhou, M. B.; Fan, J. H.; Liu, W.; Song, R. J.; Liu, Y.; Hu, M.; Xie, P.; Li, J. H. Angew. Chem. Int. Ed. 2013, 52, 3638. |
| [5] | (c) Xu, X.; Tang, Y.; Li, X.; Hong, G.; Fang, M.; Du, X. J. Org. Chem. 2014, 79, 446. |
| [5] | (d) Tang, S.; Li, Z. H.; Wang, M. W.; Li, Z. P.; Sheng, R. L. Org. Biomol. Chem. 2015, 13, 5285. |
| [5] | (e) Tang, S.; Zhou, D.; Li, Z. H.; Fu, M. J.; Jie, L.; Sheng, R. L.; Li, S. H. Synthesis. 2015, 47, 1567. |
| [6] | (a) Zheng, L.; Tao, K.; Guo, W. Adv. Synth. Catal. 2021, 363, 62. |
| [6] | (b) Li, G.; Yan, Q.; Gong, X.; Dou, X.; Yang, D. ACS Sustainable Chem. Eng. 2019, 7, 14009. |
| [6] | (c) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. Chem. Rev. 2013, 113, 5322. |
| [7] | (a) Liu, Z.; Zhong, S.; Ji, X.; Deng, G. J.; Huang, H. ACS Catal. 2021, 11, 4422. |
| [7] | (b) Yamaguchi, Y.; Seino, Y.; Suzuki, A.; Kamei, Y.; Yoshino, T.; Kojima, M.; Matsunaga, S. Org. Lett. 2022, 24, 2441. |
| [8] | (a) Cheng, H.; Lam, T. L.; Liu, Y.; Tang, Z.; Che, C. M. Angew. Chem. Int. Ed. 2021, 60, 1383. |
| [8] | (b) Liu, Z.; Zhong, S.; Ji, X.; Deng, G. J.; Huang, H. Org. Lett. 2021, 24, 349. |
| [9] | (a) Ji, W.; Tan, H.; Wang, M.; Li, P.; Wang, L. Chem. Commun. 2016, 52, 1462. |
| [9] | (b) Fan, X.; Lei, T.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2019, 21, 4153. |
| [9] | (c) Sun, Z.; Huang, H.; Wang, Q.; Huang, C.; Mao, G.; Deng, G. J. Org. Chem. Front. 2022, 9, 3506. |
| [9] | (d) Mao, L. L.; Zhou, A. X.; Zhu, X. H.; Quan, L. X.; Chen, F.; Wan, J. P.; Lai, Y. L. Org. Biomol. Chem. 2022, 20, 1196. |
| [9] | (e) Chen, L.; Ma, P.; Yang, B.; Zhao, X.; Huang, X.; Zhang, J. Chem. Commun. 2021, 57, 1030. |
| [9] | (f) Fu, W.; Xu, F.; Fu, Y.; Zhu, M.; Yu, J.; Xu, C.; Zou, D. J. Org. Chem. 2013, 78, 12202. |
| [9] | (g) Li, X.; Han, M. Y.; Wang, B.; Wang, L.; Wang, M. Org. Biomol. Chem. 2019, 17, 6612. |
| [9] | (h) Lu, M.; Zhang, T.; Tan, D.; Chen, C.; Zhang, Y.; Huang, M.; Cai, S. Adv. Synth. Catal. 2019, 361, 4237. |
| [10] | (a) Gao, F.; Yang, C.; Gao, G. L.; Zheng, L.; Xia, W. Org. Lett. 2015, 17, 3478. |
| [10] | (b) Fan, X.; Lei, T.; Chen, B.; Tung, C. H.; Wu, L. Z. Org. Lett. 2019, 21, 4153. |
| [10] | (c) Du, J.; Wang, X.; Wang, H.; Wei, J.; Huang, X.; Song, J.; Zhang, J. Org. Lett. 2021, 23, 5631. |
| [11] | (a) Xia, D.; Miao, T.; Li, P.; Wang, L. Chem. Asian J. 2015, 10, 1919. |
| [11] | (b) Jiang, Y. Q.; Li, J.; Feng, Z. W.; Xu, G. Q.; Shi, X.; Ding, Q. J.; Li, W.; Ma, C.-H.; Yu, B. Adv. Synth. Catal. 2020, 362, 2609. |
| [11] | (c) Zhang, M.; Ding, X.; Lu, A.; Kang, J.; Gao, Y.; Wang, Z.; Li, H.; Wang, Q. Org. Chem. Front. 2021, 8, 961. |
| [12] | (a) Zhong, S.; Deng, G.-J.; Dai, Z.; Huang, H. Org. Chem. Front. 2021, 8, 4419. |
| [12] | (b) Xu, Z.; Xian, N.; Chen, H.; Deng, G.-J.; Huang, H. Chin. J. Chem. 2021, 39, 1175. |
| [12] | (c) Qu, Z.; Chen, X.; Zhong, S.; Deng, G.-J.; Huang, H. Org. Lett. 2021, 23, 5349. |
| [12] | (d) Qu, Z.; Tian, T.; Tan, Y.; Ji, X.; Deng, G.-J.; Huang, H. Green Chem. 2022, 24, 7403. |
| [13] | Liu, Y.; Lin, L.; Han, Y.; Liu, Y. Chin. J. Org. Chem. 2020, 40, 4216. (in Chinese) |
| [13] | ( 刘洋, 林立青, 韩莹徽, 刘颖杰, 有机化学, 2020, 40, 4216.) |
| [14] | Shen, T.; Yuan, Y.; Song, S.; Jiao, N. Chem. Commun. 2014, 50, 4115. |
| [15] | Li, X.; Xu, X.; Hu, P.; Xiao, X.; Zhou, C. J. Org. Chem. 2013, 78, 7343-7348. |
| [16] | Liu, N. W.; Chen, Z.; Herbert, A.; Ren, H.; Manolikakes, G. Eur. J. Org. Chem. 2018, 2018, 5725. |
| [17] | Liu, J.; Zhuang, S.; Gui, Q.; Chen, X.; Yang, Z.; Tan, Z. Eur. J. Org. Chem. 2014, 2014, 3196. |
| [18] | Shi, L.; Wang, H.; Yang, H.; Fu, H. Synlett, 2015, 26, 688. |
| [19] | Zhang, M. Z.; Ji, P. Y.; Liu, Y. F.; Xu, J. W.; Guo, C. C. Adv. Synth. Catal. 2016, 358, 2976. |
| [20] | Tian, Q.; He, P.; Kuang, C. Org. Biomol. Chem. 2014, 12, 6349. |
/
| 〈 |
|
〉 |