REVIEWS

Study on the Application of Thios/Selenium Sulfonates as Radical Reagent

  • Tingting Yu ,
  • Dongxue Song ,
  • Ying Xu ,
  • Bing Liu ,
  • Ning Chen ,
  • Yingjie Liu
Expand
  • School of Pharmacy, Harbin University of Commerce, Harbin 150076

Received date: 2022-04-14

  Revised date: 2022-07-07

  Online published: 2022-09-02

Supported by

Outstanding Youth Project of Natural Science Foundation of Heilongjiang Province(YQ2019B004)

Abstract

Thios/selenium sulfonates are key structural skeletons in natural products, synthetic bioactive molecules and marketed therapeutic drugs, as well as important building material in organic synthesis, and are widely used in drug molecules and materials science. With the rapid development of transition metal-catalyzed, photocatalytic and electrocatalytic radical reactions, breakthroughs in radical chemistry have been achieved in the field of synthesis. Therefore, the applications of thios/selenium sulfonates as radical reagent have attracted extensive attention. The applications of thios/selenium sulfonates as radical reagent in metal catalysis, visible light catalysis, metal-light synergistic catalysis and other types of catalysis, which have been developed rapidly in recent years, are reviewed, and the mechanisms of some reactions are discussed in detail.

Cite this article

Tingting Yu , Dongxue Song , Ying Xu , Bing Liu , Ning Chen , Yingjie Liu . Study on the Application of Thios/Selenium Sulfonates as Radical Reagent[J]. Chinese Journal of Organic Chemistry, 2022 , 42(12) : 4202 -4219 . DOI: 10.6023/cjoc202204037

References

[1]
Ilardi, E. A.; Vitaku, E.; Njardarson, J. T. J. Med. Chem. 2014, 57, 2832.
[2]
Feng, M.; Tang, B. H.; Liang, S.; Jiang, X. Curr. Top Med. Chem. 2016, 16, 1200.
[3]
(a) Luo, J.; Zuo, Z. C.; Liu, Y. N.; Zhao, X. D. Org. Lett. 2015, 17, 3620.
[3]
(b) Kumar, S.; Sharma, N.; Maurya, I. K.; Bhasin, A. K. K.; Wangoo, N.; Brandao, P.; Fleix, V.; Bhasin, K. K.; Kumar, R. K. Eur. J. Med. Chem. 2016, 123, 916.
[3]
(c) Liao, L. H.; Guo, R. Z.; Zhao, X. D. Angew. Chem., Int. Ed. 2017, 56, 3201.
[3]
(d) Wang, X.; Wang, Q. L.; Xue, Y. R.; Sun, K.; Wu, L. L.; Zhang, B. Chem. Commun. 2020, 56, 4436.
[4]
(a) Sajomsang, W.; Tantayanon, S.; Tangpasuthadol, V.; Daly, W. H. Carbohydr. Res. 2009, 344, 2502.
[4]
(b) Guan, Q.; Han, C. M.; Zuo, D. Y.; Zhai, M. A.; Li, Z. Q.; Zhang, Q.; Zhai, Y. P.; Jiang, X. W.; Bao, K.; Wu, Y. L.; Zhang, W. G. Eur. J. Med. Chem. 2014, 87, 306.
[5]
Wang, X.; Guo, S.; Zhang, Y.; Zhang, Z. G.; Zhang, G. S.; Ye, Y.; Sun, K. Adv. Synth. Catal. 2021, 363, 3290.
[6]
Maegi, E. C.; Fu, L. B.; Nguyen, H. C. Opt. Express 2007, 15, 10324.
[7]
(a) Patra, A.; Wijsboom, Y. H.; Leitus, G.; Bendikov, M. Chem. Mater. 2011, 23, 896.
[7]
(b) Brutchey, R. L. Acc. Chem. Res. 2015, 48, 2918.
[8]
(a) Liu, H.; Jiang, X. Chem.-Asian. J. 2013, 8, 2546.
[8]
(b) Qiao, Z.; Jiang, X. Org. Biomol. Chem. 2017, 15, 1942.
[8]
(c) Kaiser, D.; Klose, I.; Oost, R.; Neuhaus, J.; Maulide, N. Chem. Rev. 2019, 119, 8701.
[9]
Sun, K.; Wang, X.; Li, C.; Wang, H.; Li, L. Org. Chem. Front. 2020, 7, 3100.
[10]
Mutra, M. R.; Kudale, V. S.; Li, J.; Tsai, W. H.; Wang, J. J. Green Chem. 2020, 22, 2288.
[11]
Fan, T.; Ma, X. L.; Liu, Y.; Jiang, C.; Xu, Y. L.; Chen, Y. Y. J. Org. Chem. 2022, 87, 5846.
[12]
(a) Sun, K.; Wang, X.; Fu, F. F.; Zhang, C.; Chen, Y.; Liu, L. Green Chem. 2017, 19, 1490.
[12]
(b) Sun, K.; Shi, Z. D.; Liu, Z. H.; Luan, B. X.; Zhu, J. L.; Xue, Y. R. Org. Lett. 2018, 20, 6687.
[13]
Sun, K.; Wang, S. G.; Feng, R. R.; Zhang, Y. X.; Wang, X.; Zhang, Z. G.; Zhang, B. Org. Lett. 2019, 21, 2052.
[14]
Wang, X.; Lei, J.; Guo, S.; Zhang, Y.; Ye, Y.; Tang, S.; Sun, K. Chem. Commun. 2022, 58, 1526.
[15]
Song, T. T.; Xu, Z. H. Sci. Sin. Chim. 2021, 51, 628.
[16]
(a) Back, T. G.; Collins, S. Tetrahedron Lett. 1980, 21, 2215.
[16]
(b) Gancarz, R. A.; Kice, J. L. Tetrahedron Lett. 1980, 21, 4155.
[17]
(a) Ghiazza, C.; Khrouz, L.; Monnereau, C.; Billard, T.; Tlili, A. Chem. Commun. 2018, 54, 9909.
[17]
(b) Li, H. Y.; Cheng, Z. R.; Tung, C. H.; Xu, Z. H. ACS Catal. 2018, 8, 8237.
[18]
Peng, Z. Y.; Yin, H. L.; Zhang, H.; Jia, T. Z. Org. Lett. 2020, 22, 5885.
[19]
Zhu, D. H.; Shao, X. X.; Hong, X.; Lu, L.; Shen, Q. L. Angew. Chem., Int. Ed. 2016, 55, 15807.
[20]
Shyam, P. K.; Son, S.; Jang, H. Y. Eur. J. Org. Chem. 2017, 2017, 5025.
[21]
Huang, S.; Thirupathi, N.; Tung, C. H.; Xu, Z. H. J. Org. Chem. 2018, 83, 9449.
[22]
Liang, Q. J.; Walsh, P. J.; Jia, T. Z. ACS Catal. 2020, 10, 2633.
[23]
Wang, F.; Chen, P.; Liu, G. Acc. Chem. Res. 2018, 51, 2036.
[24]
(a) Kharasch, M. S.; Sosnovsky, G.; Yang, N. C. J. Am. Chem. Soc. 1959, 81, 5819.
[24]
(b) Xiong, Y.; Sun, Y.; Zhang, G. Org. Lett. 2018, 20, 6250.
[25]
Xiang, J.-N.; Yuan, Y.-Q.; Guo, S.-R. Synlett 2013, 24, 443.
[26]
Wang, F.; Wang, D.; Mu, X.; Chen, P.; Liu, G. J. Am. Chem. Soc. 2014, 136, 10202.
[27]
Liu, R.; Liu, Q.; Meng, H.; Ding, H.; Hao, J.; Ji, Z.; Yue, H.; Wei, W. Org. Chem. Front. 2021, 8, 1970.
[28]
Gadde, K.; Mampuys, P.; Guidetti, A.; Ching, H. Y. V.; Herrebout, W. A.; Van Doorslaer, S.; Abbaspour Tehrani, K.; Maes, B. U. W. ACS Catal. 2020, 10, 8765.
[29]
Chen, H.; Yan, Y. Y.; Zhang, N. N.; Mo, Z, Y.; Xu, Y. L.; Chen, Y. Y. Org. Lett. 2021, 23, 376.
[30]
Liu, Y.; Zhang, N. N.; Xu, Y. L.; Chen, Y. Y. J. Org. Chem. 2021, 86, 16882.
[31]
Liu, X. Y.; Tian, S. Y.; Jiang, Y. F.; Rao, W. D.; Wang, S. Y. Org. Lett. 2021, 23, 8246.
[32]
Swarnkar, S.; Ansari, M. Y.; Kumar, A. Org. Lett. 2021, 23, 1163.
[33]
Liu, J. K.; Yao, H.; Li, X. N.; Wu, H. Y.; Lin, A. J.; Yao, H. Q.; Xu, J. Y.; Xu, S. T. Org. Chem. Front. 2020, 7, 1314.
[34]
(a) Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117.
[34]
(b) Hudlicky, T.; Reed, J. W. Angew. Chem., Int. Ed. 2010, 49, 4864.
[35]
(a) Majek, M.; Wangelin, A. J. Acc. Chem. Res. 2016, 49, 2316.
[35]
(b) Zhou, C.; Li, P.; Zhu, X. Org. Lett. 2015, 17, 6198.
[35]
(c) Majek, M.; Wangelin, A. J. Angew. Chem., Int. Ed. 2015, 54, 2270.
[36]
Dong, Y.; Ji, P.; Zhang, Y. T.; Wang, C. Q.; Meng, X.; Wang, W. Org. Lett. 2020, 22, 9562.
[37]
Li, J.; Yang, X. E.; Wang, S. L.; Zhang, L. L.; Zhou, X. Z.; Wang, S. Y.; Ji, S. J. Org. Lett. 2020, 22, 4908.
[38]
Huang, C. M.; Li, J.; Ai, J. J.; Liu, X. Y.; Rao, W. D.; Wang, S. Y. Org. Lett. 2020, 22, 9128.
[39]
(a) Wang, W. G.; Zhang, S. X.; Zhao, H. Q.; Wang, S. F. Org. Biomol. Chem. 2018, 16, 8565.
[39]
(b) Li, Y. M.; Xie, W. S.; Jiang, X. F. Chem.-Eur. J. 2015, 21, 16059.
[40]
Bi, W. Z.; Zhang, W. J.; Li, Z. J.; He, Y. H.; Feng, S. X.; Geng, Y.; Chen, X. L.; Qu, L. B. Org. Biomol. Chem. 2021, 19, 8701.
[41]
Wang, F.; Wang, S. Y. Org. Chem. Front. 2021, 8, 1976.
[42]
(a) Bahrami, K.; Khodaei, M. M.; Yousefi, B. H.; Arabi, M. S. Tetrahedron Lett. 2010, 51, 6939.
[42]
(b) Fang, Y.; Rogge, T.; Ackermann, L.; Wang, S. Y.; Ji, S. J. Nat. Commun. 2018, 9, 2240.
[43]
Patel, N. R.; Kelly, C. B.; Siegenfeld, A. P.; Molander, G. A. ACS Catal. 2017, 7, 1766.
[44]
Carta, P.; Puljic, N.; Robert, C.; Dhimane, A. L.; Ollivier, C.; Fensterbank, L.; Lacote, E.; Malacria, M. Tetrahedron Lett. 2008, 64, 11865.
[45]
(a) Xie, P. Z.; Wang, J. Y.; Liu, Y. N.; Fan, J.; Wo, X. Y.; Fu, W. S.; Sun, Z. L.; Loh, T. P. Nat. Commun. 2018, 9, 1321.
[45]
(b) Li, J.; Yang, X. E.; Wang, S. L.; Zhang, L. L.; Zhou, X. Z.; Wang, S. Y.; Ji, S. Y. Org. Lett. 2020, 22, 4908.
[46]
Li, W. Y.; Zhou, L. Green Chem. 2021, 23, 6652.
[47]
Li, F.; Pei, C.; Koenigs, R. M. Chem. Sci. 2021, 12, 6362.
[48]
Zhou, X. J.; Zhang, N. N.; Li, Y. Z.; Mo, Z. Y.; Ma, X. L.; Chen, Y. Y.; Xu, Y. L. Green Synth. Catal. 2021, 2, 397.
[49]
Li, H. Y.; Shan, C. C.; Tung, C. H.; Xu, Z. H. Chem. Sci. 2017, 8, 2610.
[50]
Zhou, X.; Peng, Z. Y.; Wang, P. G.; Liu, Q. C.; Jia, T. Z. Org. Lett. 2021, 23, 1054.
[51]
Song, T. T.; Li, H. Y.; Wei, F.; Tung, C. H.; Xu, Z. H. Tetrahedron Lett. 2019, 60, 916.
[52]
Zhang, R.; Xu, P.; Wang, S. Y.; Ji, S. J. J. Org. Chem. 2019, 84, 12324.
[53]
Back, G. T.; Collins, S.; Kerr, G. R. J. Org. Chem. 1983, 48, 3077.
[54]
Cao, L. D.; Jimeno, C.; Renaud, P. Adv. Synth. Catal. 2020, 362, 3644.
[55]
Mao, K. M.; Bian, M. W.; Dai, L.; Zhang, J. H.; Yu, Q. Y.; Wang, C.; Rong, L. C. Org. Lett. 2021, 23, 218.
[56]
Mampuys, P.; Zhu, Y. P.; Sergeyev, S.; Ruijter, E.; Orru, R. V. A.; Van Doorslaer, S.; Maes, B. U. W. Org. Lett. 2016, 18, 2808.
[57]
Zheng, Y.; He, Y.; Rong, G.; Zhang, X.; Weng, Y.; Dong, K.; Xu, X.; Mao, J. Org. Lett. 2015, 17, 5444.
[58]
Wang, X.; Stanbury, D. M. Inorg. Chem. 2006, 45, 3415.
[59]
Hwang, S. J.; Shyam, K. P.; Jang, H. Y. Bull. Korean Chem. Soc. 2018, 39, 535.
[60]
Zhang, N.; Yang, D.; Wei, W.; Yuan, L.; Cao, Y.; Wang, H. RSC Adv. 2015, 5, 37013.
[61]
Gao, J.; Lai, J.; Yuan, G. RSC Adv. 2015, 5, 66723.
[62]
Son, S.; Shyam, P. K.; Park, H.; Jeong, I.; Jang, H. Y. Eur. J. Org. Chem. 2018, 2018, 3365.
[63]
Hwang, P. K.; Shyam, P. K.; Jang, H. Y. Bull. Korean Chem. Soc. 2018, 39, 535.
[64]
Choudhuri, K.; Achar, T. K.; Mal, P. Adv. Synth. Catal. 2017, 359, 3566.
[65]
Keshari, T.; Yadav, V. K.; Srivastava, V. P.; Yadav, L. D. S. Green Chem. 2014, 16, 3986.
[66]
Murthy, S. N.; Madhav, B.; Reddy, V. P.; Rao, K. R.; Nageswar, Y. V. D. Tetrahedron Lett. 2009, 50, 5009.
[67]
Shankar, A.; Waheed, M.; Reddy, R. J. SynOpen 2021, 5, 91.
[68]
Taniguchi, N. Tetrahedron Lett. 2017, 73, 2030.
[69]
Fang, Y.; Liu, C.; Wang, F.; Ding, R.; Wang, S. Y.; Ji, S. J. Org. Chem. Front. 2019, 6, 660.
[70]
(a) Schaffner, A. P.; Montermini, F.; Pozzi, D.; Darmency, V.; Scanlan, E. M.; Renaud, P. Adv. Synth. Catal. 2008, 350, 1163.
[70]
(b) Gorokhovik, I.; Rieder, S.; Povie, G.; Renaud, P. ARKIVOC 2014, 3, 274.
[70]
(c) Wang, X.; Lei, J.; Guo, S.; Zhang, Y.; Ye, Y.; Tang, S.; Sun, K. Chem. Commun. 2022, 58, 1526.
[71]
Fang, Y.; Liu, C.; Rao, W. D.; Wang, S. Y.; Ji, S. J. Org. Lett. 2019, 21, 7687.
[72]
Wang, F.; Liu, B. X.; Rao, W. D.; Wang, S. Y. Org. Lett. 2020, 22, 6600.
Outlines

/