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

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

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.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

Fig. & Tab. 32

Scheme 1. Direct sulfenylation at α-C(sp3)—H of ethers

Scheme 2. Synthesis of thio-indole derivatives

Scheme 3. Synthesis of thio-benzofuran derivatives

Scheme 4. β-Hydroxysulfurization and β-alkoxysulfurization of styrenes

Scheme 5. Synthesis of alkyne sulfides

Scheme 6. C-3 sulfenylation of indoles

Scheme 7. Direct thiolation at indole C(sp2)—H

Scheme 8. Direct thiolation at allylic C(sp3)—H

Scheme 9. Thiolation of cycloketone oxime esters

Scheme 10. Methylthiolation of halogenated electron-rich heteroarenes

Scheme 11. Photocatalyzed arylhydrazine radical sulfenylation

Scheme 12. Synthesis of 4-thio-substituted 3,3-difluoro-γ-lactams

Scheme 13. Thioetherification of toluene and its derivatives at C(sp3)—H

Scheme 14. Synthesis of alkyl aryl thioethers through tert-butyl peroxide directly oxidative C(sp3)—H

Scheme 15. Syntheses of thiol esters by oxidative aldehydes at C(sp2)―H

Scheme 16. Synthsis of aryl methyl sulfides

Scheme 17. Synthesis of sulfone-containing oxindoles

Scheme 18. Synthesis of alkyl aryl sulfides

Scheme 19. Direct C—H thiolation of N-substituted pyrazo- lones

Scheme 20. Synthesis of thio-substituted isoquinolinones

Scheme 21. Iron-mediated synthesis of alkyl aryl sulfides

Scheme 22. Iron-catalyzed thiolation of cycloalkyl hydroperoxides

Scheme 23. Peroxide-directed C(sp3)—H thioetherification by resident silylperoxides

Scheme 24. Iron-catalyzed synthesis of sulfurated γ-lactones

Scheme 25. Cobalt-catalyzed synthesis of sulfurated oxindoles

Scheme 26. Ni-catalyzed thiolation of C(sp2)—H bonds

Scheme 27. Ni-catalyzed thiolation of aniline derivatives at C(sp2)—H

Scheme 28. Decarboxylative thiolation of RAE

Scheme 29. Silver/copper-cocatalyzed direct sulfenylation of rich arenes

Scheme 30. Copper-catalyzed thiolation of ferroceneamide

Scheme 31. Copper-mediated remote C—H bond thiolation of 8-aminoquinolines on the C5 position

Scheme 32. Copper-catalyzed the para-selective thiolation of aromatic amines

References 63

[1]	(a) Wang, N.; Saidhareddy, P.; Jiang, X. Nat. Prod. Rep. 2020, 37, 246. doi: 10.1039/C8NP00093J
	(b) Feng, M.; Tang, B.; Liang, S.; Jiang, X. Curr. Top. Med. Chem. 2016, 16, 1200. doi: 10.2174/1568026615666150915111741
	(c) Scot, K. A.; Njardarson, J. T. Top. Curr. Chem. 2018, 376, 5.
	(d) Wang, Q.; Guan, J.; Wan, J.; Li, Z. RSC Adv. 2020, 10, 24397. doi: 10.1039/D0RA04155F
	(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. doi: 10.1021/jf203772d
	(f) Devendar, P.; Yang, G.-F. Top. Curr. Chem. 2017, 375, 82.
	(g) Cinar, M. E.; Ozturk, T. Chem. Rev. 2015, 115, 3036. doi: 10.1021/cr500271a
	(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. doi: 10.1039/D2QO01699K
	(b) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K
	(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15. doi: 10.1039/D1NJ04662D
	(d) Gan, Z.; Zhu, X.; Yan, Q.; Song, X.; Yang, D. Chin. Chem. Lett. 2021, 32, 1705. doi: 10.1016/j.cclet.2020.12.046
	(e) Sun, K.; Lv, Y.; Shi, Z.; Fu, F.; Zhang, C.; Zhang, Z. Sci. China Chem. 2017, 60, 730. doi: 10.1007/s11426-016-0412-0
[3]	Chauhan, P.; Mahajan, S.; Enders, D. Chem. Rev. 2014, 114, 8807. doi: 10.1021/cr500235v pmid: 25144663
[4]	(a) Glass, R. S. Top. Curr. Chem. 2018, 376, 22.
	(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048. doi: 10.1039/C8QO01353E
	(c) Wei, Y.-F.; Gao, W.-C.; Chang, H.-H.; Jiang, X. Org. Chem. Front. 2022, 9, 6684. doi: 10.1039/D2QO01447E
[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. doi: 10.1039/D0QO01226B
	(b) Wu, R.; Huang, K.; Qiu, G.; Liu, J.-B. Synthesis 2019, 51, 3567. doi: 10.1055/s-0039-1690015
[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. doi: 10.1021/acs.chemrev.6b00620
	(b) Liu, C.; Liu, D.; Lei, A.-W. Acc. Chem. Res. 2014, 47, 3459. doi: 10.1021/ar5002044
	(c) Xu, P.; Li, W.-P.; Xie, J.; Zhu, C.-J. Acc. Chem. Res. 2018, 51, 484. doi: 10.1021/acs.accounts.7b00565
	(d) Bhunia, A.; Studer, A. Chem, 2021, 7, 2060. doi: 10.1016/j.chempr.2021.03.023
[7]	(a) Zhao, X.; Ou, Y.-C.; Liu, Y.; Maruoka, K. J.; Chen, Q. Chin. J. Org. Chem. 2021, 41, 3366. (in Chinese) doi: 10.6023/cjoc202105015 pmid: 35520400
	(赵喜, 区颖聪, 刘艳, Keiji, Maruoka, 陈迁, 有机化学, 2021, 41, 3366.) doi: 10.6023/cjoc202105015 pmid: 35520400
	(b) Guo, W.; Tao, K.; Tan, W.; Zhao, M.; Zheng, L.; Fan, X. Org. Chem. Front. 2019, 6, 2048. doi: 10.1039/C8QO01353E pmid: 35520400
	(c) Srivastava, V.; Singh, P. K.; Srivastava, A.; Singh, P. P. RSC. Adv. 2020, 10, 20046. doi: 10.1039/d0ra03086d pmid: 35520400
	(d) Yang, W.; Zhang, M.; Chen, W.; Yang, X.; Feng, J. Chin. J. Org. Chem. 2020, 40, 4060. (in Chinese) doi: 10.6023/cjoc202005039 pmid: 35520400
	(杨文超, 张明明, 陈旺, 杨小虎, 冯建国, 有机化学, 2020, 40, 4060.) doi: 10.6023/cjoc202005039 pmid: 35520400
	(e) Corce, V.; Ollivier, C.; Fensterbank, L. Chem. Soc. Rev. 2022, 51, 1470. doi: 10.1039/D1CS01084K pmid: 35520400
	(f) Wang, X.; Meng, J.; Zhao, D.; Tang, S.; Sun, K. Chin. Chem. Lett. 2023, 34, 107736. doi: 10.1016/j.cclet.2022.08.016 pmid: 35520400
[8]	Nicewicz, D. A.; MacMillan, D. W. C. Science 2008, 322, 77. doi: 10.1126/science.1161976 pmid: 18772399
[9]	(a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322. doi: 10.1021/cr300503r pmid: 30854847
	(b) Gui, Y.-Y.; Sun, L.; Lu, Z.-P.; Yu, D.-G. Org. Chem. Front. 2016, 3, 522. doi: 10.1039/C5QO00437C pmid: 30854847
	(c) Chen, J.-R.; Hu, X.-Q.; Lua, L.-Q.; Xiao, W.-J. Chem. Soc. Rev. 2016, 45, 204. pmid: 30854847
	(d) Chen, J.-R. Hu, X.-Q. Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911. doi: 10.1021/acs.accounts.6b00254 pmid: 30854847
	(e) Chen, J.-R.; Yan, D.-M.; Wei, Q.; Xiao, W.-J. ChemPhotoChem 2017, 1, 148. doi: 10.1002/cptc.v1.5 pmid: 30854847
	(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. doi: 10.1021/acs.chemrev.8b00732 pmid: 30854847
	(g) Yu, X.-Y.; Chen, J.-R.; Xiao, W.-J. Chem. Rev. 2021, 121, 506. doi: 10.1021/acs.chemrev.0c00030 pmid: 30854847
[10]	Li, J.; Zhang, J.; Tan, H.; Wang, D.-Z. Org. Lett. 2015, 17, 2522. doi: 10.1021/acs.orglett.5b01053
[11]	Zhu, X.; Xie, X.; Li, P.; Guo, J.; Wang, L. Org. Lett. 2016, 18, 1546. doi: 10.1021/acs.orglett.6b00304
[12]	Shi, Q.; Li, P.; Zhang, Y.; Wang, L. Org. Chem. Front. 2017, 4, 1322. doi: 10.1039/C7QO00152E
[13]	Li, X.-Z.; Xu, Z.-L.; Wang, L.; Wang, F.; Yang, J.-G.; Li, P. H. ChemPhotoChem 2021, 5, 142. doi: 10.1002/cptc.v5.2
[14]	Ruan, H.; Meng, L.-G.; Zhu, L.; Wang, L. Adv. Synth. Catal. 2019, 361, 3217. doi: 10.1002/adsc.v361.13
[15]	Reddy, M. B.; Anandhan, R. Chem. Commun. 2020, 56, 3781. doi: 10.1039/D0CC00815J
[16]	Ye, R.; Ruan, H.; Xu, H.; Li, Z.; Meng, L.-G.; Wang, L. Org. Chem. Front. 2021, 8, 5345. doi: 10.1039/D1QO01082D
[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. doi: 10.1039/C9GC00007K
[19]	(a) Zhou, R.; Liu, H.; Tao, H.; Yu, X.; Wu, J. Chem. Sci. 2017, 8, 4654. doi: 10.1039/C7SC00953D
	(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. doi: 10.1002/anie.v57.28
[20]	Kim, J.; Kang, B.; Hong, S. H. ACS Catal. 2020, 10, 6013. doi: 10.1021/acscatal.0c01232
[21]	(a) Boivin, J.; Fouquet, E.; Zard, S. Z. J. Am. Chem. Soc. 1991, 113, 1055. doi: 10.1021/ja00003a057
	(b) Boivin, J.; Fouquet, E.; Schiano, A.-M.; Zard, S. Z. Tetrahedron 1994, 50, 1769. doi: 10.1016/S0040-4020(01)80851-6
	(c) Boivin, J.; Fouquet, E.; Zard, S. Z. Tetrahedron 1994, 50, 1757. doi: 10.1016/S0040-4020(01)80850-4
[22]	Pratley, C.; Fenner, S.; Murphy, J. A. Chem. Rev. 2022, 122, 8181. doi: 10.1021/acs.chemrev.1c00831 pmid: 35285636
[23]	Nishimura, T.; Yoshinaka, T.; Nishiguchi, Y.; Maeda, Y.; Uemura, S. Org. Lett. 2005, 7, 2425. pmid: 15932214
[24]	Anand, D.; He, Y.; Li, L.; Zhou, L. Org. Biomol. Chem. 2019, 17, 533. doi: 10.1039/C8OB02987C
[25]	Sandfort, F.; Knecht, T.; Pinkert, T.; Daniliuc, C. G.; Glorius, F. J. Am. Chem. Soc. 2020, 142, 6913. doi: 10.1021/jacs.0c01630
[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. doi: 10.1039/C9NJ03692J
[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. doi: 10.1021/acs.joc.9b03490
[28]	Wang, L.; Liu, X.; Lin, G.; Jin, H.; Jiao, M.; Liu, X.; Luo, S. Chin. J. Org. Chem. 2023, 43, 2848. (in Chinese) doi: 10.6023/cjoc202210018
	(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.) doi: 10.6023/cjoc202210018
[29]	(a) Hong, J.; Li, M.; Zhang, J.; Sun, B.; Mo, F. ChemSusChem 2019, 12, 6. doi: 10.1002/cssc.v12.1 pmid: 35965690
	(b) Song, S.-Z.; Meng, Y.-N.; Li, Q.; Wei, W.-T. Adv. Synth. Catal. 2020, 362, 2120. doi: 10.1002/adsc.v362.11 pmid: 35965690
	(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. doi: 10.1002/anie.v60.52 pmid: 35965690
	(d) Lasso, J. D.; Castillo-Pazos, D. J.; Li, C.-J. Chem. Soc. Rev. 2021, 50, 10955. doi: 10.1039/d1cs00380a pmid: 35965690
	(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. doi: 10.1039/D2CC02661A pmid: 35965690
	(f) Golden, D. L.; Suh, S.-E.; Stahl, S. S. Nat. Rev. Chem. 2022, 6, 405. doi: 10.1038/s41570-022-00388-4 pmid: 35965690
[30]	Tang, R.-Y.; Xie, Y.-X.; Xie, Y.-L.; Xiang, J.-N.; Li, J.-H. Chem. Commun. 2011, 47, 12867. doi: 10.1039/c1cc15397h
[31]	Guo, S.-R.; Yuan, Y.-Q.; Xiang, J.-N. Org. Lett. 2013, 15, 4654. doi: 10.1021/ol402281f
[32]	Du, B.-N.; Jin, B.; Sun, P.-P. Org. Lett. 2014, 16, 3032. doi: 10.1021/ol5011449
[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. doi: 10.1039/C4GC00025K
[34]	He, C.-H.; Qian, X.-W.; Sun, P.-P. Org. Biomol. Chem. 2014, 12, 6072. doi: 10.1039/C4OB01159G
[35]	Wu, X.; Wang, Y. Tetrahedron Lett. 2018, 59, 1240. doi: 10.1016/j.tetlet.2018.02.043
[36]	Zhang, M.-Z.; Ji, P.-Y.; Liu, Y.-F.; Xu, J.-W.; Guo, C.-C. Adv. Synth. Catal. 2016, 358, 2976. doi: 10.1002/adsc.v358.18
[37]	Shahidzadeh, E. S.; Nowrouzi, N.; Abbasi, M. Appl. Organomet. Chem. 2019, 33, e5211. doi: 10.1002/aoc.v33.11
[38]	Kittikool, T.; Yotphan, S. Eur. J. Org. Chem. 2020, 2020, 961. doi: 10.1002/ejoc.v2020.8
[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. doi: 10.1002/ajoc.v10.2
[40]	(a) Yi, H.; Zhang, G.; Wang, H. M.; Huang, Z. Y.; Wang, J.; Singh, A. K.; Lei, A. Chem. Rev. 2017, 117, 9016. doi: 10.1021/acs.chemrev.6b00620
	(b) Korch, K. M.; Watson, D. A. Chem. Rev. 2019, 119, 8192. doi: 10.1021/acs.chemrev.8b00628
[41]	(a) Kosugi, M.; Shimizu, T.; Migita, T. Chem. Lett. 1978, 7, 13. doi: 10.1246/cl.1978.13
	(b) Migita, T.; Shimizu, T.; Asami, Y.; Shiobara, J.; Katoand, Y.; Kosugi, M. Bull. Chem. Soc. Jpn. 1980, 53, 1385. doi: 10.1246/bcsj.53.1385
[42]	(a) Badsara, S. S.; Cheng, C.-C.; Lee, C.-F. Asian J. Org. Chem. 2014, 3, 1197. doi: 10.1002/ajoc.v3.11 pmid: 33528480
	(b) Sundaravelu, N.; Sangeetha, S.; Sekar, G. Org. Biomol. Chem. 2021, 19, 1459. doi: 10.1039/d0ob02320e pmid: 33528480
	(c) Chen, Z.-W.; Bai, R.; Annamalai, P.; Badsara, S. S.; Lee, C.-F. New J. Chem. 2022, 46, 15. doi: 10.1039/D1NJ04662D pmid: 33528480
	(d) Huang, S.; Wang, M.; Jiang, X. Chem. Soc. Rev. 2022, 51, 8351. doi: 10.1039/D2CS00553K pmid: 33528480
[43]	(a) Bauer, I.; Knölker, H.-J. Chem. Rev. 2015, 115, 3170. doi: 10.1021/cr500425u
	(b) Wei, D.; Darcel, C. Chem. Rev. 2019, 119, 2550. doi: 10.1021/acs.chemrev.8b00372
	(c) Liang, Q.; Song, D. Chem. Soc. Rev. 2020, 49, 1209. doi: 10.1039/C9CS00508K
	(d) Rana, S.; Biswas, J.-P.; Paul, S.; Paik, A.; Maiti, D. Chem. Soc. Rev. 2021, 50, 243. doi: 10.1039/D0CS00688B
[44]	Smaligo, A. J.; Kwon, O. Org. Lett. 2019, 21, 8592. doi: 10.1021/acs.orglett.9b03186 pmid: 31573208
[45]	Sun, Q.-X.; Chen, H.; Liu, S.; Wang, X.-Q.; Duan, X.-H.; Guo, L.-N. J. Org. Chem. 2021, 86, 11987. doi: 10.1021/acs.joc.1c01366
[46]	Groendyke, B. J.; Modak, A.; Cook, S. P. J. Org. Chem. 2019, 84, 13073. doi: 10.1021/acs.joc.9b01979 pmid: 31524395
[47]	(a) Lin, J.; Song, R.-J.; Hu, M.; Li, J.-H. Chem. Rec. 2019, 19, 440. doi: 10.1002/tcr.v19.2-3
	(b) Li, Z.-L.; Fang, G.-C.; Gu, Q.-S.; Liu, X.-Y. Chem. Soc. Rev. 2020, 49, 32. doi: 10.1039/C9CS00681H
	(c) Wang, D.-K.; Li, L.; Xu, Q.; Zhang, J.; Zheng, H.; Wei, W.-T. Org. Chem. Front. 2021, 8, 7037. doi: 10.1039/D1QO01002F
[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. doi: 10.1021/acs.joc.1c00284
[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. doi: 10.1039/D2OB00877G
[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. doi: 10.1039/C4CC10431E
[51]	Omer, H. M.; Liu, P. J. Am. Chem. Soc. 2017, 139, 9909. doi: 10.1021/jacs.7b03548
[52]	Meller, T.; Ackermann, L. Chem. Eur. J. 2016, 22, 14151. doi: 10.1002/chem.v22.40
[53]	(a) Zhang, Y.; Ma, D.; Zhang, Z. Arabian J. Chem. 2022, 15, 103922. doi: 10.1016/j.arabjc.2022.103922
	(b) Parida, S. K.; Mandal, T.; Das, S.; Hota, S. K.; De Sarkar, S.; Murarka, S. ACS Catal. 2021, 11, 1640. doi: 10.1021/acscatal.0c04756
[54]	Xiao, Z.; Wang, L.; Wei, J.; Ran, C.; Liang, S.; Shang, J.; Chen, G.-Y.; Zheng, C. Chem. Commun. 2020, 56, 4164. doi: 10.1039/D0CC00451K
[55]	Li, Z.; Wang, K. F.; Zhao, X.; Ti, H.-H.; Liu, X.-G.; Wang, H.-G. Nat. Commun. 2020, 11, 5036. doi: 10.1038/s41467-020-18834-6
[56]	Yan, G.; Borah, A. J.; Wang, L. Org. Biomol. Chem. 2014, 12, 9557. doi: 10.1039/C4OB01992J
[57]	Mittal, R. K.; Aggarwal, M.; Purohit, P.; Mittal, R. K.; Aggarwal, M.; Khatana, K.; Purohit, P. Med. Chem. 2023, 19, 31. doi: 10.2174/1573406418666220303151919
[58]	Deb, M.; Singh, J.; Mallik, S.; Hazra, S.; Elias, A. J. New. J. Chem. 2017, 41, 14528. doi: 10.1039/C7NJ02388J
[59]	Sattar, M.; Shareef, M.; Patidar, K.; Kumar, S. J. Org. Chem. 2018, 83, 8241. doi: 10.1021/acs.joc.8b00974 pmid: 29878778
[60]	(a) Sasmal, S.; Dutta, U.; Lahiri, G. K.; Maiti, D. Chem. Lett. 2020, 49, 1406. doi: 10.1246/cl.200500
	(b) Sinha, S. K.; Guin, S.; Maiti, S.; Biswas, J. P.; Porey, S.; Maiti, D. Chem. Rev. 2022, 122, 5682. doi: 10.1021/acs.chemrev.1c00220
[61]	(a) Dodds, A. C.; Sutherland, A. J. Org. Chem. 2021, 86, 5922. doi: 10.1021/acs.joc.1c00448
	(b) Nalbandian, C. J.; Brown, Z. E.; Alvarez, E.; Gustafson, J. L. Org. Lett. 2018, 20, 3211. doi: 10.1021/acs.orglett.8b01066
[62]	Zhu, L.; Qiu, R.; Cao, X.; Xiao, S.; Xu, X.; Au, C.-T.; Yin, S.-F. Org. Lett. 2015, 17, 5528. doi: 10.1021/acs.orglett.5b02511
[63]	Paul, B.; Das, S.; Chatterjee, I. Org. Lett. 2023, 25, 653. doi: 10.1021/acs.orglett.2c04261

芳基二硫醚作为自由基硫试剂构建C—S键研究进展