Chinese Journal of Organic Chemistry >
Advances on the Radical Sulfonation of Alkynes
Received date: 2022-10-17
Revised date: 2022-12-19
Online published: 2023-01-05
Supported by
National Natural Science Foundation of Zhejiang Province(LY17B030011)
With sodium sulfinates, sulfonyl hydrazides, sulfinic acids, sulfonyl chlorides, dimethyl sulfoxide (DMSO) or 1,4- diazabicyclo[2.2.2]octane-1,4-diium-1,4-disulfinate (DABSO) as the sulfonyl source, which is easily formation of sulfone radical mediated by photocatalysis, electrocatalysis, metal catalysis and oxidant systems. Direct sulfone radical initiated difunctionalization of alkynes provides an efficient pathway for the synthesis of highly functionalized vinyl sulfones. According to the construction of C—X bond, the progress of involved sulfonation method in recent years is reviewed, and the difficulties and future development of this strategy are prospected.
Key words: sulfone radical; alkyne; difunctionalization; radical addition
Jiamin Ma , Jiaoxiong Li , Qiansen Meng , Xianghua Zeng . Advances on the Radical Sulfonation of Alkynes[J]. Chinese Journal of Organic Chemistry, 2023 , 43(6) : 2040 -2052 . DOI: 10.6023/cjoc202210015
| [1] | (a) Meadows, D. C.; Sanchez, T.; Neamati, N.; North, T. W.; Gervay-Hague, J. Bioorg. Med. Chem. 2007, 15, 1127. |
| [1] | (b) Dunny, E.; Doherty, W.; Evans, P.; Malthouse, J. P. G.; Nolan, D.; Knox, A. J. S. J. Med. Chem. 2013, 56, 6638. |
| [1] | (c) Woo, S. Y.; Kim, J. H.; Moon, M. K.; Han, S. H.; Yeon, S. K.; Choi, J. W.; Jang, B. K.; Song, H. J.; Kang, Y. G.; Kim, J. W.; Lee, J.; Kim, D. J.; Hwang, O.; Park, K. D. J. Med. Chem. 2014, 57, 1473. |
| [1] | (d) Noshi, M. N.; Elawa, A.; Torres, E.; Fuchs, P. L. J. Am. Chem. Soc. 2007, 129, 11242. |
| [1] | (e) Mulina, M. O.; Ilovaisky, I. A.; Parshin, D. V.; Terent'ev, O. A. Adv. Synth. Catal. 2020, 362, 4579. |
| [1] | (f) Lv, Y.; Cui, H.; Meng, N.; Yue, H.; Wei, W. Chin. Chem. Lett. 2022, 33, 97. |
| [1] | (g) Wang, X.; Meng, J.; Zhao, D.; Tang, S. Sun, K. Chin. Chem. Lett. 2023, 34, 107736. |
| [2] | (a) Fang, Y.; Luo, Z.; Xu, X. RSC Adv. 2016, 6, 59661. |
| [2] | (b) Hu, F.; Gao, W.; Chang, H.; Li, X.; Wei, W. Chin. J. Org. Chem. 2015, 35, 1848. (in Chinese) |
| [2] | (胡飞, 高文超, 常宏宏, 李兴, 魏文珑, 有机化学, 2015, 35, 1848.) |
| [3] | Truce, E. W.; Wolf, C. G. J. Org. Chem. 1971, 36, 1727. |
| [4] | Kobayashi, T.; Tanaka, Y.; Ohtani, T.; Kinoshita, H.; Inomata, K.; Kotake, H. Chem. Lett. 1987, 16, 1209. |
| [5] | Nair, V.; Augustine, A.; George, T. G.; Nair, L. G. Tetrahedron Lett. 2001, 42, 6763. |
| [6] | Katrun, P.; Chiampanichayakul, S.; Korworapan, K.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C. Eur. J. Org. Chem. 2010, 5633. |
| [7] | Li, X.; Xu, X.; Shi, X. Tetrahedron Lett. 2013, 54, 3071. |
| [8] | Wei, W.; Wen, J.; Yang, D.; Jing, H.; You, J.; Wang, H. RSC Adv. 2015, 5, 4416. |
| [9] | Luo, D.; Min, L.; Zheng, W.; Shan, L.; Wang, X.; Hu, Y. Chin. Chem. Lett. 2020, 31, 1877. |
| [10] | Sun, Y.; Abdukader, A.; Lu, D.; Zhang, H.; Liu, C. Green Chem. 2017, 19, 1255. |
| [11] | Zhou, P.; Pan, Y.; Tan, H.; Liu, W. J. Org. Chem. 2019, 84, 15662. |
| [12] | Ma, Y.; Wang, K.; Zhang, D.; Sun, P. Adv. Synth. Catal. 2019, 361, 597. |
| [13] | Zhou, C.; Zeng, X. Synthesis 2021, 53, 4614. |
| [14] | Amiel, Y. J. Org. Chem. 1974, 39, 3867. |
| [15] | Li, X.; Shi, X.; Fang, M.; Xu, X. J. Org. Chem. 2013, 78, 9499. |
| [16] | Gao, Y.; Wu, W.; Huang, Y.; Huang, K.; Jiang, H. Org. Chem. Front. 2014, 1, 361. |
| [17] | Taniguchi, N. Tetrahedron 2014, 70, 1984. |
| [18] | Wan, J.-P.; Hu, D.; Bai, F.; Wei, L.; Liu, Y. RSC Adv. 2016, 6, 73132. |
| [19] | Amiel, Y. J. Org. Chem. 1971, 36, 3691. |
| [20] | Liu, X.; Duan, X.; Pan, Z.; Han, Y. Liang, Y. Synlett 2005, 1752. |
| [21] | Chen, B.; Xia, X.; Zeng, X.; Xu, B. Tetrahedron Lett. 2018, 59, 3950. |
| [22] | Zeng, X.; IIies, L.; Nakamura, E. Org. Lett. 2012, 14, 954. |
| [23] | Wang, L.; Zhu, H.; Che, J.; Yang, Y.; Zhu, G. Tetrahedron Lett. 2014, 55, 1011. |
| [24] | Chakrasali, P.; Kim, K.; Jung, Y.-S.; Kim, H.; Han, S. B. Org. Lett. 2018, 20, 7509. |
| [25] | Hossain, A.; Engl, S.; Lutsker, E.; Reiser, O. ACS Catal. 2019, 9, 1103. |
| [26] | Henriquez, A. M.; Engl, S.; Jaque, P.; Gonzalez, A. I.; Natali, M.; Reiser, O. Cabrera, R. A. Eur. J. Inorg. Chem. 2021, 4020. |
| [27] | Zeng, K.; Chen, L.; Chen, Y.; Liu, Y.; Zhou, Y.; Au, C.-T.; Yin, S.-F. Adv. Synth. Catal. 2017, 359, 841. |
| [28] | Liu, X.-T.; Ding, Z.-C.; Ju, L.-C.; Xu, S.-X.; Zhan, Z.-P. Synthesis 2017, 49, 1757. |
| [29] | Xu, Y.; Zhao, J.; Tang, X.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2014, 356, 2029. |
| [30] | Rong, G.; Mao, J.; Yan, H.; Zheng, Y.; Zhang, G. J. Org. Chem. 2015, 80, 7652. |
| [31] | Meesin, J.; Katrun, P.; Reutrakul, V.; Pohmakotr, M.; Soorukram, D.; Kuhakarn, C. Tetrahedron 2016, 72, 1440. |
| [32] | Wei, W.; Li, J.; Yang, D.; Wen, J.; Jiao, Y.; You, J. Wang, H. Org. Biomol. Chem. 2014, 12, 1861. |
| [33] | Li, S.; Li, X.; Yang, F.; Wu, Y. Org. Chem. Front. 2015, 2, 1076. |
| [34] | Rong, G.; Mao, J.; Yan, H.; Zheng, Y.; Zhang, G. J. Org. Chem. 2015, 80, 4697. |
| [35] | Liu, T.; Ding, Y.; Fan, X.; Wu, J. Org. Chem. Front. 2018, 5, 3153. |
| [36] | Lu, Q.; Zhang, J.; Zhao, G.; Qi, Y.; Wang, H.; Lei, A. J. Am. Chem. Soc. 2013, 135, 11481. |
| [37] | Handa, S.; Fennewald, C. J.; Lipshutz, H. B. Angew. Chem., Int. Ed. 2014, 53, 3432. |
| [38] | Singh, K. A.; Chawla, R.; Yadav, S. L. D. Tetrahedron Lett. 2014, 55, 2845. |
| [39] | Xiong, Y.-S.; Weng, J.; Lu, G. Adv. Synth. Catal. 2018, 360, 1611. |
| [40] | Kumar, N.; Kumar, A. ACS Sustainable Chem. Eng. 2019, 7, 9182. |
| [41] | Cai, S.; Chen, D.; Xu, Y.; Weng, W.; Li, L.; Zhang, R.; Huang, M. Org. Biomol. Chem. 2016, 14, 4205. |
| [42] | Dam, B.; Sahoo, K. A.; Patel, K. B. Green Chem. 2022, 24, 7122. |
| [43] | Yavari, I.; Shaabanzadeh, S. Org. Lett. 2020, 22, 464. |
| [44] | Ansari, Y. M.; Kumar, N.; Kumar, A. Org. Lett. 2019, 21, 3931. |
| [45] | Du, W.-B.; Wang, N.-N.; Pan, C.; Ni, S.-F.; Wen, L.-R.; Li, M.; Zhang, L.-B. Green Chem. 2021, 23, 2420. |
| [46] | Sahoo, A. K.; Dahiya, A.; Das, B.; Behera, A.; Patel, B. K. J. Org. Chem. 2021, 86, 11968. |
| [47] | Xie, W.; Ma, P.; Zhang, Y.; Xi, L.; Qiu, S.; Huang, X.; Yang, B.; Gao, Y.; Zhang, J. Org. Lett. 2022, 24, 6099. |
| [48] | Kataoka, T.; Banno, Y.; Watanabe, S.-I.; Iwamura, T.; Shimizu, H. Tetrahedron Lett. 1997, 38, 1809. |
| [49] | Dai, C.; Wang, J.; Deng, S.; Zhou, C.; Zhang, W.; Zhu, Q.; Tang, X. RSC Adv. 2017, 7, 36112. |
| [50] | Fu, H.; Shang, J.-Q.; Yang, T.; Shen, Y.; Gao, C.-Z.; Li, Y.-M. Org. Lett. 2018, 20, 489. |
| [51] | Liu, Z.; Yang, L.; Zhang, K.; Chen, W.; Yu, T.; Wang, L.; Gao, W.; Tang, B. Org. Lett. 2020, 22, 2081. |
| [52] | Wang, Y.; Tang, K.; Liu, Z.; Ning, Y. Chem. Commun. 2020, 56, 13141. |
| [53] | Li, H.; Cheng, Z.; Tung, C.-H.; Xu, Z. ACS Catal. 2018, 8, 8237. |
| [54] | Song, T.; Li, H.; Wei, F.; Tung, C.-H.; Xu, Tetrahedron Lett. 2019, 60, 916. |
| [55] | Peng, Z.; Yin, H.; Zhang, H.; Jia, T. Org. Lett. 2020, 22, 5885. |
| [56] | Zhang, M.; Zeng, X. Org. Lett. 2021, 23, 3326. |
| [57] | Wang, Z.; Zhang, Z.; Zhao, W.; Sivaguru, P.; Zanoni, G.; Wang, Y.; Anderson, A. E.; Bi, X. Nat. Commun. 2021, 12, 5244. |
| [58] | Zhang, Z.; Song, Q.; Feng, C.; Wang, Z.; Zhao, W.; Ning, Y.; Wu, Y. Chem. Asian J. 2022, 17, e202200299. |
| [59] | Qian, H.; Huang, X. Tetrahedron Lett. 2002, 43, 1059. |
| [60] | Liu, Y.; Zheng, G.; Li, Y.; Zhang, Q. J. Org. Chem. 2017, 82, 2269. |
| [61] | Sun, K. Wang, X.; Fu, F.; Zhang, C.; Chen, Y.; Liu, L. Green Chem. 2017, 19, 1490. |
| [62] | Sun, K.; Shi, Z, Liu, Z.; Luan, B,; Zhu, J.; Xue, Y. Org. Lett. 2018, 20, 6687. |
| [63] | Zhang, R.; Xu, P.; Wang, S.-Y.; Ji, S.-J. J. Org. Chem. 2019, 84, 12324. |
| [64] | Ning, Y.; Ji, Q.; Liao, P.; Anderson, A. E.; Bi, X. Angew. Chem., Int. Ed. 2017, 56, 13805. |
| [65] | Ansari, Y. M.; Swarnkar, S.; Kumar, A. Chem. Commun. 2020, 56, 9561. |
| [66] | Rohokale, S. R.; Tambeb, D. S.; Kshirsagar, A. U. Org. Biomol. Chem. 2018, 16, 536. |
| [67] | He, X.; Yue, X.; Zhang, L.; Wu, S.; Hu, M.; Li, J.-H. Chem. Commun. 2019, 55, 3517. |
| [68] | Qi, Z.; Jiang, Y.; Wang, Y.; Yan, R. J. Org. Chem. 2018, 83, 8636. |
| [69] | Wang, B.; Yan, Z.; Liu, L.; Wang, J.; Zha, Z.; Wang, Z. Green Chem. 2019, 21, 205. |
| [70] | Zheng, L.; Wang, Z.; Li, C.; Wu, Y.; Liu, Z.; Ning, Y. Chem. Commun. 2020, 56, 9874. |
| [71] | Li, Y.; Xiang, Y.; Li, Z.; Wu, J. Org. Chem. Front. 2016, 3, 1493. |
| [72] | Xiang, Y.; Li, Y.; Kuang, Y.; Wu, J. Adv. Synth. Catal. 2017, 359, 2605. |
| [73] | Xiang, Y.; Li, Y.; Kuang, Y.; Wu, J. Chem.-Eur. J. 2017, 23, 1032. |
| [74] | García-Domínguez, A.; Müller, S.; Nevado, C. Angew. Chem., Int. Ed. 2017, 56, 9949. |
| [75] | Dong, X.; Jiang, W.; Hua, D.; Wang, X.; Xu, L.; Wu, X. Chem. Sci. 2021, 12, 11762. |
| [76] | Liu, L.; Sun, K.; Su, L.; Dong, J.; Cheng, L.; Zhu, X.; Au, C.-T.; Zhou, Y.; Yin, S.-F. Org. Lett. 2018, 20, 4023. |
| [77] | Sun, Q.; Li, L.; Liu, L.; Guan, Q.; Yang, Y.; Zha, Z.; Wang, Z. Org. Lett. 2018, 20, 5592. |
| [78] | Sun, Q.; Li, L.; Liu. L.; Yang, Y.; Zha, Z.; Wang, Z. Sci. China Chem. 2019, 62, 904. |
| [79] | Xie, S.; Li, Y.; Liu, P.; Sun, P. Org. Lett. 2020, 22, 8774. |
| [80] | Yao, Y.; Yin, Z.; He, F.-S.; Qin, X.; Xie, W.; Wu, J. Chem. Commun. 2021, 57, 2883. |
| [81] | Liang, Y.-Q.; Xu, Y.-X.; Cai, Z.-J.; Ji, S.-J. Chem. Commun. 2022, 58, 10206. |
/
| 〈 |
|
〉 |