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2023 , Vol. 43 >Issue 11: 3728 - 3744

DOI: https://doi.org/10.6023/cjoc202305005

综述与进展

芳基二硫醚作为自由基硫试剂构建C—S键研究进展

  • 程飞 ,
  • 孙琪雯 ,
  • 卢江溶 ,
  • 王兴兰 ,
  • 张吉泉
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  • a 贵州医科大学药学院 贵阳 550025
    b 贵州医科大学 贵州省化学合成药物研发利用工程技术研究中心 贵阳 550025

收稿日期: 2023-05-06

  修回日期: 2023-06-21

  网络出版日期: 2023-07-13

基金资助

国家自然科学基金(22267003); 贵州省自然科学基金(ZK[2023]305); 贵州省卫健委科技基金(gzwkj2023-511); 贵州省高等学校大学生创新训练计划(S202210660143); 贵州医科大学优秀青年人才计划([2022]102)

收起

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)

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摘要

含硫化合物在医药、农业、天然产物和有机材料等方面有广泛的应用, 因而引起了科研人员极大的兴趣, 开发高效、绿色的含硫化合物的构建和转化方法具有重要意义. 近年来, 稳定、低毒的芳基二硫醚类化合物作为刺激性强、毒性大的硫醇类化合物的理想替代物, 为各种含硫化合物的构建开辟了一条新的途径. 从光催化、非金属参与和过渡金属催化三个方面分类综述了芳基二硫醚作为自由基硫试剂构建C—S键的研究进展.

关键词： 芳基二硫醚; C—S键的构建; 自由基; 绿色合成

本文引用格式

程飞 , 孙琪雯 , 卢江溶 , 王兴兰 , 张吉泉 . 芳基二硫醚作为自由基硫试剂构建C—S键研究进展[J]. 有机化学, 2023 , 43(11) : 3728 -3744 . DOI: 10.6023/cjoc202305005

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.

Key words： aryl disulfides; C—S bond formation; radical; green-synthesis

参考文献

[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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