SIOC 中文
CJOG
Adv search

Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 4: 1283 - 1296

DOI: https://doi.org/10.6023/cjoc202407024

ARTICLES

Efficient Synthesis of Diaryl Sulfides via Three Component Cross Coupling

  • Mengqin Liu ,
  • Yiting Chen ,
  • Juyuan Zhang ,
  • Heye Zhou ,
  • Tao Qin ,
  • Bin Liu
Expand
  • a College of Materials and Chemical Engineering, China Three Gorges University, Yichang, Hubei 443002
    b Hubei Three Gorges Laboratory, Yichang, Hubei 443007
* E-mail: ;
*

Received date: 2024-09-04

  Revised date: 2024-10-10

  Online published: 2024-11-08

Supported by

National Natural Science Foundation of China(22201158); Programme of Introducing Talents of Discipline to Universities (111 Project); Programme of Introducing Talents of Discipline to Universities(D20015); Hubei Provincial Natural Science Foundation(2024AFB212); Hubei Provincial Natural Science Foundation(2024AFB152)

Fold

Abstract

Diaryl sulfides are found in drugs and natural products, yet their synthesis traditionally requires metal-catalyzed cross-coupling reactions, high temperatures, and the use of the air-sensitive and extremely odorous thiophenols. A novel transition-metal-free strategy for the synthesis of unsymmetric diaryl sulfides via a three-component cross-coupling of polyfluoro- arenes, diaryliodide salts and potassium thioacetate is reported. This approach enables the formation of a diverse array of unsymmetric diaryl thioethers through two successive electrophilic substitution reactions involving commercially available potassium thioacetate and two electron-deficient aromatic hydrocarbons, demonstrating broad substrate scope and functional group compatibility. Additionally, this strategy facilitates the synthesis of sulfones and sulfoxides via a one-pot oxidation reaction, thereby extending its applicability. Gram-scale reactions and derivatization experiments have shown excellent results, further proving the potential application value of this reaction. Mechanistic insights were elucidated through control, radical inhibition and intermediate capture experiments.

Key words： transition metal-free; polyfluoroarenes; diaryliodonium salts; diaryl sulfides

Cite this article

Mengqin Liu , Yiting Chen , Juyuan Zhang , Heye Zhou , Tao Qin , Bin Liu . Efficient Synthesis of Diaryl Sulfides via Three Component Cross Coupling[J]. Chinese Journal of Organic Chemistry, 2025 , 45(4) : 1283 -1296 . DOI: 10.6023/cjoc202407024

References

[1]
(a) Liu, H.; Fujiwara, T.; Nishikawa, T.; Mishima, Y.; Nagai, H.; Shida, T.; Tachibana, K.; Kobayashi, H.; Mangindaan, R. E.; Namikoshi, M. Tetrahedron 2005, 61, 8611.
[1]
(b) Nakazawa, T.; Xu, J.; Nishikawa, T.; Oda, T.; Fujita, A.; Ukai, K.; Mangindaan, R. E.; Rotinsulu, H.; Kobayashi, H.; Namikoshi, M. J. Nat. Prod. 2007, 70, 439.
[1]
(c) Dunbar, K. L.; Scharf, D. H.; Litomska, A.; Hertweck, C. Chem. Rev. 2017, 117, 5521.
[1]
(d) Iino, H.; Usui, T.; Hanna, J. Nat. Commun. 2015, 6, 1.
[1]
(e) Roy, K. M. Ullmann?s Encycl. Ind. Chem. 2000, 36, 625.
[2]
Mao, Y.; Jiang, L.; Chen, T.; He, H.; Liu, G.; Wang, H. Synthesis 2015, 47, 1387.
[3]
Chekal, B. P.; Guinness, S. M.; Lillie, B. M.; McLaughlin, R. W.; Palmer, C. W.; Post, R. J.; Sieser, J. E.; Singer, R. A.; Sluggett, G. W.; Vaidyanathan, R. Org. Process Res. Dev. 2014, 18, 266.
[4]
Moreno, E.; Calvo, A.; Schwartz, J.; Navarro-Blasco, I.; González-Pe?as, E.; Sanmartín, C.; Irache, J. M.; Espuelas, S. Pharmaceutics 2019, 11, 607.
[5]
Scott, K. A.; Njardarson, J. T. Top. Curr. Chem. 2018, 376, 1.
[6]
(a) Shen, C.; Zhang, P.; Sun, Q.; Bai, S.; Hor, T. S. A.; Liu, X. Chem. Soc. Rev. 2015, 44, 291.
[6]
(b) Zhang, B.; Kang, Y.; Shi, R. Chin. J. Org. Chem. 2016, 36, 1814 (in Chinese).
[6]
(张变香, 亢永强, 史瑞雪, 有机化学, 2016, 36, 1814.)
[6]
(c) Abedinifar, F.; Bahadorikhalili, S.; Larijani, B.; Mahdavi, M.; Verpoort, F. Appl. Organomet. Chem. 2022, 36, e6482.
[6]
(d) Qin, S. Chin. J. Org. Chem. 2023, 43, 3761 (in Chinese).
[6]
(秦思凝, 有机化学, 2023, 43, 3761.)
[6]
(e) Parumala, S. K. R.; Surasani, S. R.; Peddinti, R. K. New J. Chem. 2014, 38, 5268.
[6]
(f) Zhou, Q.; Zhang, B.; Gu, H.; Zhong, A.; Du, T.; Zhou, Q.; Ye, Y.; Jin, Z.; Jiang, H.; Chen, R. Lett. Org. Chem. 2012, 9, 175.
[6]
(g) Zhang, Y.; Wang, Y.; Wang, L.; Han, J. Org. Biomol. Chem. 2024, 22, 486.
[7]
Jang, H. Org. Biomol. Chem. 2021, 19, 8656.
[8]
(a) Li, Y.; Liu, L.; Shan, D.; Liang, F.; Wang, S.; Yu, L.; Liu, J.-Q.; Wang, Q.; Shao, X.; Zhu, D. ACS Catal. 2023, 13, 13474.
[8]
(b) Liu, Y.; Xing, S.; Zhang, J.; Liu, W.; Xu, Y.; Zhang, Y.; Yang, K.; Yang, L.; Jiang, K.; Shao, X. Org. Chem. Front. 2022, 9, 1375.
[8]
(c) Zhang, W.; Huang, M.; Zou, Z.; Wu, Z.; Ni, S.; Kong, L.; Zheng, Y.; Wang, Y.; Pan, Y. Chem. Sci. 2021, 12, 2509.
[8]
(d) Gra?l, S.; Hamze, C.; Koller, T. J.; Knochel, P. Chem.-Eur. J. 2019, 25, 3752.
[8]
(e) Dong, Z.-B.; Balkenhohl, M.; Tan, E.; Knochel, P. Org. Lett. 2018, 20, 7581.
[8]
(f) Wang, X.; Meng, J.; Zhao, D.; Tang, S.; Sun, K. Chin. Chem. Lett. 2023, 34, 107736.
[9]
(a) Wang, X.; Chen, J.-Q.; Yang, X.-X.; Hao, E.-J.; Dong, Z.-B. Eur. J. Org. Chem. 2022, e202200015.
[9]
(b) Li, F.; Wang, D.; Chen, H.; He, Z.; Zhou, L.; Zeng, Q. Chem. Commun. 2020, 56, 13029.
[9]
(c) Zou, L.-H.; Zhao, C.; Li, P.-G.; Wang, Y.; Li, J. J. Org. Chem. 2017, 82, 12892.
[9]
(d) Prasad, C. D.; Balkrishna, S. J.; Kumar, A.; Bhakuni, B. S.; Shrimali, K.; Biswas, S.; Kumar, S. J. Org. Chem. 2013, 78, 1434.
[9]
(e) Fernández-Salas, J. A.; Pulis, A. P.; Procter, D. J. Chem. Commun. 2016, 52, 12364.
[9]
(f) Xia, D.; Luo, J.; He, L.; Cai, Z.; Du, G. Chin. J. Org. Chem. 2024, 44, 622 (in Chinese).
[9]
(夏登鹏, 罗锦昀, 何林, 蔡志华, 杜广芬, 有机化学, 2024, 44, 622.)
[10]
(a) Bacchi, S.; Benaglia, M.; Cozzi, F.; Demartin, F.; Filippini, G.; Gavezzotti, A. Chem.-Eur. J. 2006, 12, 3538.
[10]
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
[10]
(c) Berger, R.; Resnati, G.; Metrangolo, P.; Weber, E.; Hulliger, J. Chem. Soc. Rev. 2011, 40, 3496.
[10]
(d) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.
[10]
(e) Yoshimura, A.; Zhdankin, V. V. Chem. Rev. 2016, 116, 3328.
[11]
(a) Liu, C.; Zhang, B. Chem. Rec. 2016, 16, 667.
[11]
(b) Li, X.; Fu, B.; Zhang, Q.; Yuan, X.; Zhang, Q.; Xiong, T.; Zhang, Q. Angew. Chem., Int. Ed. 2020, 59, 23056.
[11]
(c) Zhao, Y.; Fu, B.; Wang, S.; Li, Y.; Yuan, X.; Yin, J.; Xiong, T. Zhang, Q. Org. Lett. 2023, 25, 2492.
[11]
(d) Linde, E.; Bulfield, D.; Kervefors, G.; Purkait, N.; Olofsson, B. Chem 2022, 8, 850.
[11]
(e) Stuart, D. R. Chem.-Eur. J. 2017, 23, 15852.
[11]
(f) Fa?anás-Mastral, M. Synthesis 2017, 49, 1905.
[12]
(a) Yang, L.; Qin, T.; Liu, B. Synlett 2023, 34, 2336.
[12]
(b) Liao, W.; Du, H.; Chen, M.; Xiong, Y.; Zhou, H.; Qin, T.; Liu, B. Org. Biomol. Chem. 2024, 22, 708.
[13]
(a) Fortugno, C.; Varchi, G.; Guerrini, A. Biomed. Anal. 2014, 95, 151.
[13]
(b) Gambini, L.; Udompholkul, P.; Salem, A. F.; Baggio, C.; Pellecchia, M. ChemMedChem 2020, 15, 2176.
[13]
(c) Tang, X.; Zhang, N.; He, G.; Li, C.-H.; Huang, W.; Wang, X.-Y.; Zhan, G.; Han, B. Org. Lett. 2020, 22, 7909.
[14]
(a) Mondal, S.; Di Tommaso, E. M.; Olofsson, B. Angew. Chem., Int. Ed. 2023, 62, No. e202216296.
[14]
(b) Wu, S.; Wong, T. H.-F.; Righi, P.; Melchiorre, P. J. Am. Chem. Soc. 2024, 146, 2907.
[15]
Wang, D.; Yu, X.; Zhao, K.; Li, L.; Ding, Y. Tetrahedron Lett. 2014, 55, 5739.
Options
Outlines

/

〈 〉