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Chinese Journal of Organic Chemistry >

2022 , Vol. 42 >Issue 9: 2940 - 2946

DOI: https://doi.org/10.6023/cjoc202201046

ARTICLES

Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates

  • Jianming Zhao ,
  • Jiashun Zhu ,
  • Jiabin Shen ,
  • Yilan Zhang ,
  • Wanmei Li
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  • Key Laboratory of Organosilicon Chemistry and Material Technology of Ministry of Education, College of Material, Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou 311121
* Corresponding author. E-mail:

Received date: 2022-01-27

  Revised date: 2022-04-21

  Online published: 2022-06-01

Supported by

Natural Science Foundation of Zhejiang Province(LY21B060009); “Ten-Thousand Talents Plan” of Zhejiang Province(2019R51012)

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Abstract

Photocatalysis has become the forefront of international chemical research due to its green and environmentally friendly characteristics. A new protocol to construct S—S(O)2 bonds using selectfluor as oxidant and eosin Y as photocatalyst under blue light irradiation was reported. This method has advantages of mild conditions, good compatibility of functional groups, and easily preparation of various symmetric or asymmetric thiosulfonates various from the corresponding mercaptans with good conversion rates. Thus, this protocol provides a very valuable reference for developing a catalytic system with mild conditions, high atomic economy and strong universality to achieve efficient and controllable conversion of sulfur-containing organic compounds.

Key words： thiol; photocatalysis; oxidative coupling; thiosulfonate

Cite this article

Jianming Zhao , Jiashun Zhu , Jiabin Shen , Yilan Zhang , Wanmei Li . Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates[J]. Chinese Journal of Organic Chemistry, 2022 , 42(9) : 2940 -2946 . DOI: 10.6023/cjoc202201046

References

[1]
Wang, N. Z.; Saidhareddy, P.; Jiang, X. F. Nat. Prod. Rep. 2020, 37, 246.
[2]
Colomer, I.; Velado, M.; de la Pradilla, R. F.; Viso, A. Chem. Rev. 2017, 117, 4201.
[3]
Reddy, R. J.; Ball-Jones, M. P.; Davies, P. W. Angew. Chem., Int. Ed. 2017, 56, 13310.
[4]
Merchant, R. R.; Edwards, J. T.; Qin, T.; Kruszyk, M. M.; Bi, C.; Che, G. D.; Bao, D. H.; Qiao, W. H.; Sun, L. J.; Collins, M. R.; Fadeyi, O. O.; Gallego, G. M.; Mousseau, J. J.; Nuhant, P.; Baran, P. S. Science 2018, 360, 75.
[5]
Mampuys, P.; McElroy, C. R.; Clark, J. H.; Orru, R. V. A.; Maes, B. U. W. Adv. Synth. Catal. 2020, 362, 3.
[6]
(a) Steudel, R. Chem. Rev. 2002, 102, 3905.
[6]
(b) Smith, M.; Hunter, R.; Stellenboom, N.; Usza, D. A.; Parker, M. I.; Hammouda, A. N. H.; Jackson, G.; Kaschula, C. H. Biochim. Biophys. Acta, Gen. Subj. 2016, 1860, 1439.
[6]
(c) Mai, S. Y.; Song, Q. L. Angew. Chem., Int. Ed. 2017, 56, 7952.
[7]
(a) 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.
[7]
(b) Li, M.; Zheng, N.; Li, J.; Zheng, Y.; Song, W. Green Chem. 2020, 22, 23942.
[7]
(c) Li, J.; Li, M.; Duan, X.; Song, W. Tetrahedron Lett. 2020, 61, 152256.
[8]
(a) Sara, S.; Sima, A.; Mahdi, F. M. Synlett 2011, 319.
[8]
(b) Iranpoor, N.; Mohajer, D.; Rezaeifard, A.-R. Tetrahedron Lett. 2004, 45, 3811.
[9]
Zheng, Y.; Qing, F.-L.; Huang, Y.; Xu, X.-H. Adv. Synth. Catal. 2016, 358, 3477.
[10]
(a) Yang, F.-L.; Tian, S.-K. Angew. Chem. 2013, 125, 5029.
[10]
(b) Kumaraswamy, G.; Raju, R. Adv. Synth. Catal. 2014, 356, 2591.
[10]
(c) Wang, T.-T.; Yang, F.-L.; Tian, S.-K. Adv. Synth. Catal. 2015, 357, 928.
[10]
(d) Wang, F.-X.; Tian, S.-K. J. Org. Chem. 2015, 80, 12697.
[10]
(e) Singh, R.; Allam, B. K.; Singh, N.; Kumari, K.; Singh, S. K.; Singh, K. N. Org. Lett. 2015, 17, 2656.
[10]
(f) Pang, X.; Xiang, L.; Yang, X.; Yan, R. Adv. Synth. Catal. 2016, 358, 321.
[10]
(g) Yang, Y.; Zhang, S.; Tang, L.; Hu, Y.; Zha, Z.; Wang, Z. Green Chem. 2016, 18, 2609.
[11]
(a) Liang, G.; Chen, J.; Chen, J.; Li, W.; Chen, J.; Wu, H. Tetrahedron Lett. 2012, 53, 6768.
[11]
(b) Cao, L.; Luo, S.-H.; Jiang, K.; Hao, Z.-F.; Wang, B.-W.; Pang, C.-M.; Wang, Z.-Y. Org. Lett. 2018, 20, 4754.
[12]
Xu, H.; Zhang, Y.-F.; Lang, X. Chin. Chem. Lett. 2020, 6, 1520.
[13]
Sheng, W.; Shi, J.-L.; Hao, H.; Li, X.; Lang, X. J. Colloid Interface Sci. 2020, 565, 614.
[14]
He, J.; Chen, G.; Zhang, B.; Li, Y.; Chen, J.-R.; Xiao, W.-J.; Liu, F.; Li, C. Chem 2020, 6, 1149.
[15]
Masayuki, K.; Sayuri, N.; Yuki, N., Yuki, I.; Toshiaki, I.; Haruka, T.; Tomomi, O.; Honoka, H.; Yukari, K., Mari, K.; Kento, Y.; Takuya, N.; Shiro, Y. Tetrahedron 2014, 70, 2464.
[16]
Liang, X.; Xiong, M.; Zhu, H.; Shen, K.; Pan, Y. J. Org. Chem. 2019, 84, 11210.
[17]
Chen, Z.; Liu, C.; Liu, J.; Li, J.; Xi, S.; Chi, X.; Xu, H.; Park, I.-H.; Peng, X.; Xing, L; Yu, W.; Liu, X.; Zhong, L.; Leng, K.; Huang, W. Adv. Mater. 2020, 32, 1906437.
[18]
Cai, M.-T.; Lv, G.-S.; Chen, J.-X.; Gao, W.-X.; Ding, J.-C.; Wu, H.-Y. Chem. Lett. 2010, 39, 368.
[19]
Reddy, R.; Kumar, J.; Kumari, A. Eur. J. Org. Chem. 2019, 2019, 3771.
[20]
Natarajan, P. Tetrahedron Lett. 2015, 56, 4131.
[21]
Lv, M.; Liu, Y.; Li, K.; Yang, G. Synlett 2021, 32, 81.
[22]
Kim, J.; Par, S.; Kim, H.; Kim, J. Tetrahedron Lett. 2020, 61, 152112.
[23]
Strehl, J.; Hilt, G. Eur. J. Org. Chem. 2022, 2022, 35.
[24]
Nair, A. M.; Kumar, S.; Halder, I.; Volla, C. M. R. Org. Biomol. Chem. 2019, 17, 5897.
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