Research Progress on the Construction of C—S Bond Using Aryl Disulfides as Radical Sulfur Reagents

  • Fei Cheng ,
  • Qiwen Sun ,
  • Jiangrong Lu ,
  • Xinglan Wang ,
  • Jiquan Zhang
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  • a School of Pharmaceutical Sciences, Guizhou Medical University, Guiyang 550025
    b Guizhou Provincial Engineering Technology Research Center for Chemical Drug R&D,Guizhou Medical University, Guiyang 550025
* E-mail:

Received date: 2023-05-06

  Revised date: 2023-06-21

  Online published: 2023-07-13

Supported by

National Natural Science Foundation of China(22267003); Guizhou Provincial Natural Science Foundation(ZK[2023]305); Science and Technology Fund of Guizhou Provincial Health Commission(gzwkj2023-511); Guizhou Provincial Undergraduate Innovation and Entrepreneurship Training Program(S202210660143); Excellent Young Talents Plan of Guizhou Medical University([2022]102)

Abstract

Sulfur-containing compounds have been widely applied in numerous natural products, pharmaceuticals, agrochemicals, and organic functional materials, which has attracted great interest among researchers. Therefore, it is of great significance to develop efficient and green methods for the construction and transformation of sulfur-containing compounds. In recent years, stable and low-toxicity aryl disulfides have been used as ideal substitutes for thiol compounds endured with strong irritation and toxicity, which has opened up a new path for the construction of various sulfur-containing compounds. In this paper, the research progress of aryl disulfides as radical sulfur reagents to build C—S bond is reviewed, which is divided into three parts: photocatalysis, non-metallic participation, and transition metal catalysis.

Cite this article

Fei Cheng , Qiwen Sun , Jiangrong Lu , Xinglan Wang , Jiquan Zhang . Research Progress on the Construction of C—S Bond Using Aryl Disulfides as Radical Sulfur Reagents[J]. Chinese Journal of Organic Chemistry, 2023 , 43(11) : 3728 -3744 . DOI: 10.6023/cjoc202305005

References

[1]
(a) Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246.
[1]
(b) Feng, M.; Tang, B.; Liang, S.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200.
[1]
(c) Scot, K. A.; Njardarson, J. T. Top. Curr. Chem. 2018, 376, 5.
[1]
(d) Wang, Q.; Guan, J.; Wan, J.; Li, Z. RSC Adv. 2020, 10, 24397.
[1]
(e) Xu, W. M.; Han, F. F.; He, M.; Hu, D. Y.; He, J.; Yang, S.; Song, B. A. J. Agric. Food Chem. 2012, 60, 1036.
[1]
(f) Devendar, P.; Yang, G.-F. Top. Curr. Chem. 2017, 375, 82.
[1]
(g) Cinar, M. E.; Ozturk, T. Chem. Rev. 2015, 115, 3036.
[1]
(h) Turkoglu, G.; Cinar, M. E.; Ozturk, T. Top. Curr. Chem. 2017, 375, 84.
[2]
(a) Dong, B.; Shen, J.; Xie, L.-G. Org. Chem. Front. 2023, 10, 1322.
[2]
(b) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351.
[2]
(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15.
[2]
(d) Gan, Z.; Zhu, X.; Yan, Q.; Song, X.; Yang, D. Chin. Chem. Lett. 2021, 32, 1705.
[2]
(e) Sun, K.; Lv, Y.; Shi, Z.; Fu, F.; Zhang, C.; Zhang, Z. Sci. China Chem. 2017, 60, 730.
[3]
Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev. 2014, 114, 8807.
[4]
(a) Glass, R. S. Top. Curr. Chem. 2018, 376, 22.
[4]
(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048.
[4]
(c) Wei, Y.-F.; Gao, W.-C.; Chang, H.-H.; Jiang, X. Org. Chem. Front. 2022, 9, 6684.
[5]
(a) Batista, G. M. F.; de Castro, P. P.; dos Santos, J. A.; Skrydstrup, T.; Amarante, G. W. Org. Chem. Front. 2021, 8, 326.
[5]
(b) Wu, R.; Huang, K.; Qiu, G.; Liu, J.-B. Synthesis 2019, 51, 3567.
[6]
(a) Yi, H.; Zhang, G.-T.; Wang, H.-M.; Huang, Z.-Y.; Wang, J.; Singh, A. K.; Lei, A.-W. Chem. Rev. 2017, 117, 9016.
[6]
(b) Liu, C.; Liu, D.; Lei, A.-W. Acc. Chem. Res. 2014, 47, 3459.
[6]
(c) Xu, P.; Li, W.-P.; Xie, J.; Zhu, C.-J. Acc. Chem. Res. 2018, 51, 484.
[6]
(d) Bhunia, A.; Studer, A. Chem, 2021, 7, 2060.
[7]
(a) Zhao, X.; Ou, Y.-C.; Liu, Y.; Maruoka, K. J.; Chen, Q. Chin. J. Org. Chem. 2021, 41, 3366. (in Chinese)
[7]
(赵喜, 区颖聪, 刘艳, Keiji, Maruoka, 陈迁, 有机化学, 2021, 41, 3366.)
[7]
(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048.
[7]
(c) Srivastava, V.; Singh, P. K.; Srivastava, A.; Singh, P. P. RSC. Adv. 2020, 10, 20046.
[7]
(d) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese)
[7]
(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.)
[7]
(e) Corce, V.; Ollivier, C.; Fensterbank, L. Chem. Soc. Rev. 2022, 51, 1470.
[7]
(f) Wang, X.; Meng, J.; Zhao, D.; Tang, S.; Sun, K. Chin. Chem. Lett. 2023, 34, 107736.
[8]
Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77.
[9]
(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
[9]
(b) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522.
[9]
(c) Chen, J.-R.; Hu, X.-Q.; Lua, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 204.
[9]
(d) Chen, J.-R. Hu, X.-Q. Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911.
[9]
(e) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148.
[9]
(f) Troian-Gautier, L.; Turlington, M. D.; Wehlin, S. A. M.; Maurer, A. B.; Brady, M. D.; Swords, W. B.; Meyer, G. J. Chem. Rev. 2019, 119, 4628.
[9]
(g) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506.
[10]
Li, J.; Zhang, J.; Tan, H.; Wang, D.-Z. Org. Lett. 2015, 17, 2522.
[11]
Zhu, X.; Xie, X.; Li, P.; Guo, J.; Wang, L. Org. Lett. 2016, 18, 1546.
[12]
Shi, Q.; Li, P.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322.
[13]
Li, X.-Z.; Xu, Z.-L.; Wang, L.; Wang, F.; Yang, J.-G.; Li, P. H. ChemPhotoChem 2021, 5, 142.
[14]
Ruan, H.; Meng, L.-G.; Zhu, L.; Wang, L. Adv. Synth. Catal. 2019, 361, 3217.
[15]
Reddy, M. B.; Anandhan, R. Chem. Commun. 2020, 56, 3781.
[16]
Ye, R.; Ruan, H.; Xu, H.; Li, Z.; Meng, L.-G.; Wang, L. Org. Chem. Front. 2021, 8, 5345.
[17]
Ye, L.-M.; Chen, J.; Mao, P.; Zhang, X.-J.; Yan, M. Tetrahedron Lett. 2017, 58, 2743.
[18]
Rathore, V.; Kumar, S. Green. Chem. 2019, 21, 2670.
[19]
(a) Zhou, R.; Liu, H.; Tao, H.; Yu, X.; Wu, J. Chem. Sci. 2017, 8, 4654.
[19]
(b) Fan, X.-Z.; Rong, J.-W.; Wu, H.-L.; Zhou, Q.; Deng, H.-P.; Tan, J. D.; Xue, C.-W.; Wu, L.-Z.; Tao, H.-R.; Wu, J. Angew. Chem., Int. Ed. 2018, 57, 8514.
[20]
Kim, J.; Kang, B.; Hong, S. H. ACS Catal. 2020, 10, 6013.
[21]
(a) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055.
[21]
(b) Boivin, J.; Fouquet, E.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1994, 50, 1769.
[21]
(c) Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1757.
[22]
Pratley, C.; Fenner, S.; Murphy, J. A. Chem. Rev. 2022, 122, 8181.
[23]
Nishimura, T.; Yoshinaka, T.; Nishiguchi, Y.; Maeda, Y.; Uemura, S. Org. Lett. 2005, 7, 2425.
[24]
Anand, D.; He, Y.; Li, L.; Zhou, L. Org. Biomol. Chem. 2019, 17, 533.
[25]
Sandfort, F.; Knecht, T.; Pinkert, T.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2020, 142, 6913.
[26]
Li, R.; Shi, T.; Chen, X.-L.; Lv, Q.-Y.; Zhang, Y.-L.; Peng, Y.-Y.; Qu, L.-B.; Yu, B. New J. Chem. 2019, 43, 13642.
[27]
Ye, Z.-P.; Xia, P.-J.; Liu, F.; Hu, Y.-Z.; Song, D.; Xiao, J.-A.; Huang, P.; Xiang, H.-Y.; Chen, X.-Q.; Yang, H. J. Org. Chem. 2020, 85, 5670.
[28]
Wang, L.; Liu, X.; Lin, G.; Jin, H.; Jiao, M.; Liu, X.; Luo, S. Chin. J. Org. Chem. 2023, 43, 2848. (in Chinese)
[28]
(王灵娜, 刘晓庆, 林钢, 金泓颖, 焦民均, 刘雪粉, 罗书平, 有机化学, 2023, 43, 2848.)
[29]
(a) Hong, J.; Li, M.; Zhang, J.; Sun, B.; Mo, F. ChemSusChem 2019, 12, 6.
[29]
(b) Song, S.-Z.; Meng, Y.-N.; Li, Q.; Wei, W.-T. Adv. Synth. Catal. 2020, 362, 2120.
[29]
(c) Qiao, J.; Song, Z.-Q.; Huang, C.; Ci, R.-N.; Liu, Z.; Chen, B.; Tung, C.-H.; Wu, L.-Z. Angew. Chem., Int. Ed. 2021, 60, 27201.
[29]
(d) Lasso, J. D.; Castillo-Pazos, D. J.; Li, C.-J. Chem. Soc. Rev. 2021, 50, 10955.
[29]
(e) Zhang, Y.; Sahoo, P. K.; Ren, P.; Qin, Y.; Cauwenbergh, R.; Nimmegeers, P.; SivaRaman, G.; Van Passel, S.; Guidetti, A.; Das, S. Chem. Commun. 2022, 58, 11454.
[29]
(f) Golden, D. L.; Suh, S.-E.; Stahl, S. S. Nat. Rev. Chem. 2022, 6, 405.
[30]
Tang, R.-Y.; Xie, Y.-X.; Xie, Y.-L.; Xiang, J.-N.; Li, J.-H. Chem. Commun. 2011, 47, 12867.
[31]
Guo, S.-R.; Yuan, Y.-Q.; Xiang, J.-N. Org. Lett. 2013, 15, 4654.
[32]
Du, B.-N.; Jin, B.; Sun, P.-P. Org. Lett. 2014, 16, 3032.
[33]
Zeng, J.-W.; Liu, Y.-C.; Hsieh, P.-A.; Huang, Y.-T.; Yi, C.-L.; Badsara, S. S.; Lee, C.-F. Green Chem. 2014, 16, 2644.
[34]
He, C.-H.; Qian, X.-W.; Sun, P.-P. Org. Biomol. Chem. 2014, 12, 6072.
[35]
Wu, X.; Wang, Y. Tetrahedron Lett. 2018, 59, 1240.
[36]
Zhang, M.-Z.; Ji, P.-Y.; Liu, Y.-F.; Xu, J.-W.; Guo, C.-C. Adv. Synth. Catal. 2016, 358, 2976.
[37]
Shahidzadeh, E. S.; Nowrouzi, N.; Abbasi, M. Appl. Organomet. Chem. 2019, 33, e5211.
[38]
Kittikool, T.; Yotphan, S. Eur. J. Org. Chem. 2020, 2020, 961.
[39]
Wang, X.-L.; Bai, X.; Wu, C.-F.; Dong, Y.-X.; Zhang, M.; Fan, L.-L.; Tang, L.; Yang, Y.-Y.; Zhang, J.-Q. Asian J. Org. Chem. 2021, 10, 386.
[40]
(a) Yi, H.; Zhang, G.; Wang, H. M.; Huang, Z. Y.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016.
[40]
(b) Korch, K. M.; Watson, D. A. Chem. Rev. 2019, 119, 8192.
[41]
(a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 7, 13.
[41]
(b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Katoand, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385.
[42]
(a) Badsara, S. S.; Cheng, C.-C.; Lee, C.-F. Asian J. Org. Chem. 2014, 3, 1197.
[42]
(b) Sundaravelu, N.; Sangeetha, S.; Sekar, G. Org. Biomol. Chem. 2021, 19, 1459.
[42]
(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15.
[42]
(d) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351.
[43]
(a) Bauer, I.; Kn?lker, H.-J. Chem. Rev. 2015, 115, 3170.
[43]
(b) Wei, D.; Darcel, C. Chem. Rev. 2019, 119, 2550.
[43]
(c) Liang, Q.; Song, D. Chem. Soc. Rev. 2020, 49, 1209.
[43]
(d) Rana, S.; Biswas, J.-P.; Paul, S.; Paik, A.; Maiti, D. Chem. Soc. Rev. 2021, 50, 243.
[44]
Smaligo, A. J.; Kwon, O. Org. Lett. 2019, 21, 8592.
[45]
Sun, Q.-X.; Chen, H.; Liu, S.; Wang, X.-Q.; Duan, X.-H.; Guo, L.-N. J. Org. Chem. 2021, 86, 11987.
[46]
Groendyke, B. J.; Modak, A.; Cook, S. P. J. Org. Chem. 2019, 84, 13073.
[47]
(a) Lin, J.; Song, R.-J.; Hu, M.; Li, J.-H. Chem. Rec. 2019, 19, 440.
[47]
(b) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32.
[47]
(c) Wang, D.-K.; Li, L.; Xu, Q.; Zhang, J.; Zheng, H.; Wei, W.-T. Org. Chem. Front. 2021, 8, 7037.
[48]
Cheng, F.; Wang, L.-L.; Mao, Y.-H.; Dong, Y.-X.; Liu, B.; Zhu, G.-F.; Yang, Y.-Y.; Guo, B.; Tang, L.; Zhang, J.-Q. J. Org. Chem. 2021, 86, 8620.
[49]
Cheng, F.; Bai, X.; Sun, Q.-W.; Zhu, G.-F.; Dong, Y.-X.; Yang, Y.-Y.; Gao, X.-L.; Guo, B.; Tang, L.; Zhang, J.-Q. Org. Biomol. Chem. 2022, 20, 6423.
[50]
Yang, K.; Wang, Y.-Q.; Chen, X.-Y.; Kadi, A.-A.; Fun, H.-K.; Sun, H.; Zhang, Y.; Lu, H.-J. Chem. Commun. 2015, 51, 3582.
[51]
Omer, H. M.; Liu, P. J. Am. Chem. Soc. 2017, 139, 9909.
[52]
Meller, T.; Ackermann, L. Chem. Eur. J. 2016, 22, 14151.
[53]
(a) Zhang, Y.; Ma, D.; Zhang, Z. Arabian J. Chem. 2022, 15, 103922.
[53]
(b) Parida, S. K.; Mandal, T.; Das, S.; Hota, S. K.; De Sarkar, S.; Murarka, S. ACS Catal. 2021, 11, 1640.
[54]
Xiao, Z.; Wang, L.; Wei, J.; Ran, C.; Liang, S.; Shang, J.; Chen, G.-Y.; Zheng, C. Chem. Commun. 2020, 56, 4164.
[55]
Li, Z.; Wang, K. F.; Zhao, X.; Ti, H.-H.; Liu, X.-G.; Wang, H.-G. Nat. Commun. 2020, 11, 5036.
[56]
Yan, G.; Borah, A. J.; Wang, L. Org. Biomol. Chem. 2014, 12, 9557.
[57]
Mittal, R. K.; Aggarwal, M.; Purohit, P.; Mittal, R. K.; Aggarwal, M.; Khatana, K.; Purohit, P. Med. Chem. 2023, 19, 31.
[58]
Deb, M.; Singh, J.; Mallik, S.; Hazra, S.; Elias, A. J. New. J. Chem. 2017, 41, 14528.
[59]
Sattar, M.; Shareef, M.; Patidar, K.; Kumar, S. J. Org. Chem. 2018, 83, 8241.
[60]
(a) Sasmal, S.; Dutta, U.; Lahiri, G. K.; Maiti, D. Chem. Lett. 2020, 49, 1406.
[60]
(b) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682.
[61]
(a) Dodds, A. C.; Sutherland, A. J. Org. Chem. 2021, 86, 5922.
[61]
(b) Nalbandian, C. J.; Brown, Z. E.; Alvarez, E.; Gustafson, J. L. Org. Lett. 2018, 20, 3211.
[62]
Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C.-T.; Yin, S.-F. Org. Lett. 2015, 17, 5528.
[63]
Paul, B.; Das, S.; Chatterjee, I. Org. Lett. 2023, 25, 653.
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