Citation: Mengjie Song, Qingyue Hu, Zheng-Yi Li, Xiaoqiang Sun, Ke Yang. NFSI-catalyzed S–S bond exchange reaction for the synthesis of unsymmetrical disulfides[J]. Chinese Chemical Letters, ;2022, 33(9): 4269-4272. doi: 10.1016/j.cclet.2021.12.073 shu

NFSI-catalyzed S–S bond exchange reaction for the synthesis of unsymmetrical disulfides

Mengjie Song ^a ,
Qingyue Hu ^a ,
Zheng-Yi Li ^{a, *,} ,
Xiaoqiang Sun ^b ,
Ke Yang ^{a, *,}

a.
Jiangsu Key Laboratory of Advanced Catalytic Materials & Technology, School of Petrochemical Engineering, Changzhou University, Changzhou 213164, China
b.
Institute of Urban & Rural Mining, Changzhou University, Changzhou 213164, China

zyli@cczu.edu.cn

keyang@cczu.edu.cn

Received Date: 17 October 2021
Revised Date: 26 December 2021
Accepted Date: 28 December 2021
Available Online: 2 January 2022

Figures(6)

The metal-free S–S bond exchange reaction of symmetrical disulfides catalyzed by NFSI is described. This novel protocol provides a facile and efficient approach to accessing important unsymmetrical disulfides. Furthermore, this strategy could also be utilized in the late-stage functionalization of amino acids, drugs, and natural products. The broad substrate scope, good functional group tolerance and easy accessibility of catalyst indicate that this strategy affords a green and practical complementary method to various unsymmetrical disulfides.
- Metal-free,
- S–S bond exchange,
- NFSI,
- Unsymmetrical disulfides,
- Organic synthesis
1. [1]
  D. Nielsen, N. Shepherd, W. Xu, et al., Chem. Rev. 117 (2017) 8094–8128. doi: 10.1021/acs.chemrev.6b00838
2. [2]
  M. Feng, B. Tang, S. Liang, X. Jiang, Curr. Top. Med. Chem. 16 (2016) 1200–1216. doi: 10.2174/1568026615666150915111741
3. [3]
  F. Silva, S. Khokhar, D. Williams, et al., Angew. Chem. Int. Ed. 57 (2018) 12290–12293. doi: 10.1002/anie.201808605
4. [4]
  N. Wang, P. Saidhareddy X. Jiang, Nat. Prod. Rep. 37 (2020) 246–275. doi: 10.1039/c8np00093j
5. [5]
  M. Góngora-Benítez, J. Tulla-Puche, F. Albericio, Chem. Rev. 114 (2014) 901–926. doi: 10.1021/cr400031z
6. [6]
  H. Xu, Y.F. Zhang, X. Lang, Chin. Chem. Lett. 31 (2020) 1520–1524. doi: 10.1016/j.cclet.2019.10.024
7. [7]
  X. Qiu, X. Yang, Y. Zhang, S. Song, N. Jiao, Org. Chem. Front. 6 (2019) 2220–2225. doi: 10.1039/c9qo00239a
8. [8]
  A. Parida, K. Choudhuri, P. Mal, Chem. Asian J. 14 (2019) 2579–2583. doi: 10.1002/asia.201900620
9. [9]
  M. Musiejuk, D. Witt, Org. Prep. Proced. Int. 47 (2015) 95–131. doi: 10.1080/00304948.2015.1005981
10. [10]
  M. Oka, D. Katsube, T. Tsuji, H. Iida, Org. Lett. 22 (2020) 9244–9248. doi: 10.1021/acs.orglett.0c03458
11. [11]
  P. Huang, P. Wang, S. Tang, Z. Fu, A. Lei, Angew. Chem. Int. Ed. 57 (2018) 8115–8119. doi: 10.1002/anie.201803464
12. [12]
  D. Dethe, A. Srivastava, B. Dherange, B. Kumar, Adv. Synth. Catal. 360 (2018) 3020–3025. doi: 10.1002/adsc.201800405
13. [13]
  Y. Dou, X. Huang, H. Wang, et al., Green Chem. 19 (2017) 2491–2495. doi: 10.1039/C7GC00401J
14. [14]
  J.K. Vandavasi, W.P. Hu, C.Y. Chen, J.J. Wang, Tetrahedron 67 (2011) 8895–8901. doi: 10.1016/j.tet.2011.09.071
15. [15]
  L. Delarue-Bizzini, P. Zwick, M. Mayor, Eur. J. Org. Chem. 2019 (2019) 6956–6960. doi: 10.1002/ejoc.201901283
16. [16]
  N. Taniguchi, Tetrahedron, 73 (2017) 2030–2035. doi: 10.1016/j.tet.2017.02.047
17. [17]
  X. Xiao, M. Feng, X. Jiang, Chem. Commun. 51 (2015) 4208–4211. doi: 10.1039/C4CC09633A
18. [18]
  D. Wang, Q. He, K. Shi, et al., Adv. Synth. Catal. 363 (2021) 2767–2772. doi: 10.1002/adsc.202100165
19. [19]
  D. Wang, Y. Gao, Y. Tong, et al., Adv. Synth. Catal. 362 (2020) 4991–4995. doi: 10.1002/adsc.202000851
20. [20]
  D. Wang, X. Liang, M. Xiong, et al., Org. Biomol. Chem. 18 (2020) 4447–4451. doi: 10.1039/d0ob00804d
21. [21]
  M. Arisawa, M. Yamaguchi, J. Am. Chem. Soc. 125 (2003) 6624–6625. doi: 10.1021/ja035221u
22. [22]
  K. Tanaka, K. Ajiki, Tetrahedron Lett. 45 (2004) 5677–5679. doi: 10.1016/j.tetlet.2004.05.092
23. [23]
  R. Caraballo, M. Rahm, P. Vongvilai, T. Brinck, O. Ramström, Chem. Commun. (2008) 6603–6605. doi: 10.1039/b815710c
24. [24]
  R.D. Crocker, M.A. Hussein, J. Ho, T.V. Nguyen, Chem. Eur. J. 23 (2017) 6259–6263. doi: 10.1002/chem.201700744
25. [25]
  Y. Xu, X. Shi, L. Wu, RSC Adv. 9 (2019) 24025–24029. doi: 10.1039/c9ra04242c
26. [26]
  J. Xue, X. Jiang, Org. Lett. 22 (2020) 8044–8048. doi: 10.1021/acs.orglett.0c02992
27. [27]
  W. Gao, J. Tian, Y. Shang, X. Jiang, Chem. Sci. 11 (2020) 3903–3908. doi: 10.1039/d0sc01060j
28. [28]
  J. Zou, J. Chen, T. Shi, et al., ACS Catal. 9 (2019) 11426–11430. doi: 10.1021/acscatal.9b04326
29. [29]
  W. Wang, Y. Lin, Y. Ma, C. Tung, Z. Xu, Org. Lett. 20 (2018) 3829–3832. doi: 10.1021/acs.orglett.8b01418
30. [30]
  X. Xiao, J. Xue, X. Jiang, Nat. Commun. 9 (2018) 1–9. doi: 10.1155/2018/7042105
31. [31]
  X. Xiao, M. Feng, X. Jiang, Angew. Chem. Int. Ed. 55 (2016) 14121–14125. doi: 10.1002/anie.201608011
32. [32]
  C. Park, B. Johnson, J. Duan, et al., Org. Lett. 18 (2016) 904–907. doi: 10.1021/acs.orglett.5b03557
33. [33]
  Z. Wu, D. Pratt, J. Am. Chem. Soc. 142 (2020) 10284–10290. doi: 10.1021/jacs.0c03626
34. [34]
  S.P. Black, J.K.M. Sanders, A.R. Stefankiewicz, Chem. Soc. Rev. 43 (2014) 1861–1872. doi: 10.1039/C3CS60326A
35. [35]
  P.T. Corbett, J. Leclaire, L. Vial, et al., Chem. Rev. 106 (2006) 3652–3711. doi: 10.1021/cr020452p
36. [36]
  Y. Kim, C.J. Li, Green Synth. Catal. 1 (2020) 1–11. doi: 10.1016/j.gresc.2020.06.002
37. [37]
  W. Wang, W. Chen, J. Luo, P. Xie, Chin. J. Org. Chem. 41 (2021) 543–552. doi: 10.6023/cjoc202006069
38. [38]
  Q. Gu, E. Vessally, RSC Adv. 10 (2020) 16756–16768. doi: 10.1039/d0ra00324g
39. [39]
  K. Yang, S. Dai, Z. Li, Z.Y. Li, Q. Sun, Org. Chem. Front. 8 (2021) 4974–4979. doi: 10.1039/d1qo00774b
40. [40]
  K. Yang, Y. Li, M. Song, et al., Chin. Chem. Lett. 32 (2021) 146–149. doi: 10.1016/j.cclet.2020.11.036
41. [41]
  Y. Li, Q.Y. Hu, F.Y. Zhang, et al., ChemistrySelect 6 (2021) 6268–6271. doi: 10.1002/slct.202101925
42. [42]
  K. Yang, M. Song, A. Ali, S. Mudassir, H. Ge, Chem. Asian J. 15 (2020) 729–741. doi: 10.1002/asia.202000011
43. [43]
  K. Yang, B. Niu, Z. Ma, et al., J. Org. Chem. 84 (2019) 14045–14052. doi: 10.1021/acs.joc.9b02202
44. [44]
  K. Yang, Y. Li, H. Zhang, et al., Eur. J. Org. Chem. 2019 (2019) 5812–5814. doi: 10.1002/ejoc.201900960
45. [45]
  K. Yang, M. Song, Z. Ma, et al., Org. Chem. Front. 6 (2019) 3996–3999. doi: 10.1039/c9qo01073d
46. [46]
  K. Yang, H. Zhang, B. Niu, S. Mudassir, H. Ge, Eur. J. Org. Chem. 2018 (2018) 5520–5523. doi: 10.1002/ejoc.201801090
47. [47]
  J. Li, C. Ma, D. Xing, W. Hu, Org. Lett. 21 (2019) 2101–2105. doi: 10.1021/acs.orglett.9b00382
48. [48]
  Z. Deng, J. Wei, L. Liao, H. Huang, X. Zhao, Org. Lett. 17 (2015) 1834–1837. doi: 10.1021/acs.orglett.5b00213
49. [49]
  H. Mei, J. Liu, R. Pajkert, G.V. Röschenthaler, J. Han, Org. Biomol. Chem. 18 (2020), 3761–3766. doi: 10.1039/d0ob00720j
50. [50]
  A. Liu, J. Liu, H. Mei, G.V. Röschenthaler, J. Han, Chin. J. Org. Chem. 40 (2020), 1926–1933. doi: 10.6023/cjoc202003004
51. [51]
  P. Zhou, C. Chen, S. Li, J. Chem. Res. 44 (2020) 376–380. doi: 10.1177/1747519820902670
52. [52]
  M. Kirihara, S. Naito, Y. Nishimura, et al., Tetrahedron 70 (2014), 2464–2471. doi: 10.1016/j.tet.2014.02.013
53. [53]
  M. Kirihara, S. Naito, Y. Ishizuka, H. Hanai, T. Noguchi, Tetrahedron Lett. 52 (2011) 3086–3089. doi: 10.1016/j.tetlet.2011.03.132
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