Citation: Zhang Faguang, Peng Xing, Ma Jun'an. Recent Advances in the Synthesis of CF₃-Substituted Triazoles and Tetrazoles[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 109-116. doi: 10.6023/cjoc201808007 shu

Recent Advances in the Synthesis of CF₃-Substituted Triazoles and Tetrazoles

Tianjin Key Laboratory of Molecular Optoelectronic Sciences, and Tianjin Collaborative Innovation Center of Chemical Science & Engineering, Department of Chemistry, Tianjin University, Tianjin 300072

Corresponding author: Zhang Faguang, zhangfg1987@tju.edu.cn Ma Jun'an, majun_an68@tju.edu.cn
Received Date: 7 August 2018
Revised Date: 14 September 2018
Available Online: 12 January 2018
Fund Project: the National Natural Science Foundation of China 21772142the National Natural Science Foundation of China 21532008the National Basic Research Program of China 973 Program, No. 2014CB745100Project supported by the National Natural Science Foundation of China (Nos. 21472137, 21532008, 21772142) and the National Basic Research Program of China (973 Program, No. 2014CB745100)the National Natural Science Foundation of China 21472137

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Trifluoromethylated triazoles and tetrazoles have emerged as increasingly important heterocycles in pharmaceuticals, agrochemicals, catalysis, and materials. As a consequence, great attention has been paid to the efficient synthesis of these valuable CF₃-containing molecules. Herein, the advances in the past decade towards the synthesis of CF₃-substituted triazoles and tetrazoles are summarized. The remarkable progress in the utilization of versatile CF₃-functionalized building blocks including CF₃-containing alkynes, CF₃-containing carbonyl compounds, CF₃-containing pyrones and trifluorodiazoethane (CF₃CHN₂) is demonstrated accordingly.
- trifluoromethyl group,
- triazole,
- tetrazole,
- fluorine-containing heterocycle,
- cycloaddition
1. [1]
  (a) Herr, R. J. Bioorg. Med. Chem. 2002, 10, 3379.
  (b) Krivopalov, V. P.; Shkurko, O. P. Russ. Chem. Rev. 2005, 74, 339.
  (c) Myznikov, L. V.; Hrabalek, A.; Koldobskii, G. I. Chem. Heterocycl. Compd. 2007, 43, 1.
  (d) Muller, T.; Bäse, S. Angew. Chem., Int. Ed. 2011, 50, 11844.
  (e) Chattopadhyay, B.; Gevorgyan, V. Angew. Chem., Int. Ed. 2012, 51, 862.
  (f) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
  (g) Thirumurugan, P.; Matosiuk, D.; Jozwiak, K. Chem. Rev. 2013, 113, 4905.
2. [2]
3. [3]
  (a) Rosa, M. D. L.; Kim, H. W.; Gunic, E.; Jenket, C.; Boyle, U.; Koh, Y.; Korboukh, I.; Allan, M.; Zhang, W.; Chen, H.; Xu, W.; Nilar, S.; Yao, N.; Hamatake, R.; Lang, S. A.; Hong, Z.; Zhang, Z.; Girardet, J.-L. Bioorg. Med. Chem. Lett. 2006, 16, 4444.
  (b) Gakh, A. A.; Kirk, K. L. Fluorinated Heterocycles, ACS Symposium Series, American Chemical Society, Washington, DC, 2009.
  (c) Petrov, V. A. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry, and Applications, John Wiley & Sons, Hoboken, NJ, 2009.
  (d) Kanishchev, O. S.; Gudz, G. P.; Shermolovich, Y. G.; Nesterova, N. V.; Zagorodnya, S. D.; Golovan, A. V. Nucleosides Nucleotides Nucleic Acids 2011, 30, 768.
  (e) Sugane, T.; Tobe, T.; Hamaguchi, W.; Shimada, I.; Maeno, K.; Miyata, J.; Suzuki, T.; Kohara, A.; Kimizuka, T.; Morita, T.; Doihara, H.; Saita, K.; Aota, M.; Furutani, M.; Shimada, Y.; Hamada, N.; Sakamoto, S.; Tsukamoto, S. J. Med. Chem. 2011, 54, 387.
  (f) Gakh, A. A.; Shermolovich, Y. Curr. Top. Med. Chem. 2014, 14, 952.
4. [4]
  (a) Huisgen, R. 1, 3-Dipolar Cycloaddition Chemistry, Wiley, New York, 1984, pp. 1~176.
  (b) Rostovtsev, V. V.; Green, L. G.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 2596.
  (c) Meldal, M.; Tornoe, C. W. Chem. Rev. 2008, 108, 2952.
  (d) Boren, B. C.; Narayan, S.; Rasmussen, L. K.; Zhang, L.; Zhao, H.; Lin, Z.; Jia, G.; Fokin, V. V. J. Am. Chem. Soc. 2008, 130, 8923.
  (e) Spiteri, C.; Moses, J. E. Angew. Chem., Int. Ed. 2010, 49, 31.
  (f) Hein, J. E.; Fokin, V. V. Chem. Soc. Rev. 2010, 39, 1302.
5. [5]
  (a) Carpenter, W.; Haymaker, A.; Moore, D. W. J. Org. Chem. 1966, 31, 789.
  (b) Meazza, G.; Zanardi, G. J. Fluorine Chem. 1991, 55, 199.
6. [6]
  (a) Zhang, C.-T.; Zhang, X.; Qing, F.-L. Tetrahedron Lett. 2008, 49, 3927.
  (b) Hager, C.; Miethchen, R.; Reinke, H. J. Fluorine Chem. 2000, 104, 135.
  (c) Xiong, Z.; Qiu, X.-L.; Huang, Y.; Qing, F.-L. J. Fluorine Chem. 2011, 132, 166.
  (d) Granqvist, L.; Virta, P. J. Org. Chem. 2015, 80, 7961.
7. [7]
  Wei, J.; Chen, J.; Xu, J.; Cao, L.; Deng, H.; Sheng, W.; Zhang, H.; Cao, W. J. Fluorine Chem. 2012, 133, 146. doi: 10.1016/j.jfluchem.2011.09.009
8. [8]
  Funabiki, K.; Noma, N.; Kuzuya, G.; Matsui, M.; Shibata, K. J. Chem. Res. 1999, 300.
9. [9]
  Sibgatulin, D. A.; Bezdudny, A. V.; Mykhailiuk, P. K.; Voievoda, N. M.; Kondratov, I. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 1075.
10. [10]
  Roberts, L. R.; Bradley, P. A.; Bunnage, M. E.; England, K. S.; Fairman, D.; Fobian, Y. M.; Fox, D. N. A.; Gymer, G. E.; Heasley, S. E.; Molette, J.; Smith, G. L.; Schmidt, M. A.; Tones, M. A. A.; Dack, K. N. Bioorg. Med. Chem. Lett. 2011, 21, 6515. doi: 10.1016/j.bmcl.2011.08.071
11. [11]
  Chen, M.; Wang, X.-F.; Wang, S.-S.; Feng, Y.-X.; Chen, F.; Yang, C.-L. J. Fluorine Chem. 2012, 135, 323. doi: 10.1016/j.jfluchem.2011.12.015
12. [12]
  Peng, W.; Zhu, S. Tetrahedron 2003, 59, 4395. doi: 10.1016/S0040-4020(03)00621-5
13. [13]
  (a) Danence, L. J. T.; Gao, Y.; Li, M.; Huang, Y.; Wang, J. Chem.- Eur. J. 2011, 17, 3584.
  (b) Rozin, Y. A.; Leban, J.; Dehaen, W.; Nenajdenko, V. G.; Muzalevskiy, V. M.; Eltsov, O. S.; Bakulev, V. A. Tetrahedron 2012, 68, 614.
  (c) Bonacorso, H. G.; Moraes, M. C.; Wiethan, C. W.; Luz, F. M.; Meyer, A. R.; Zanatta, N.; Martins, M. A. P. J. Fluorine Chem. 2013, 156, 112.
  (d) Pokhodylo, N. T.; Shyyka, O. Y.; Matiychuk, V. S.; Obushak, M. D.; Pavlyuk, V. V. ChemistrySelect 2017, 2, 5871.
14. [14]
  (a) Zhang, J.; Jin, G.; Xiao, S.; Wu, J.; Cao, S. Tetrahedron 2013, 69, 2352.
  (b) Raeppel, S. L.; Raeppel, F.; Therrien, E. Bioorg. Med. Chem. Lett. 2015, 25, 2527.
15. [15]
  (a) Goel, A.; Ram, V. J. Tetrahedron 2009, 65, 7865.
  (b) Usachev, B. I. J. Fluorine Chem. 2015, 175, 36.
  (c) Pratap, R.; Ram, V. J. Tetrahedron 2017, 73, 2529.
16. [16]
  (a) Usachev, B. I.; Usachev, S. A.; Röschenthaler, G.-V.; Sosnovskikh, V. Y. Tetrahedron Lett. 2011, 52, 6723.
  (b) Usachev, S. A.; Usachev, B. I.; Eltsov, O. S.; Sosnovskikh, V. Y. Tetrahedron 2014, 70, 8863.
  (c) Sosnovskikh, V. Y.; Usachev, B. I. Mendeleev Commun. 2002, 12, 75.
17. [17]
  Wang, S.; Yang, L.-J.; Zeng, J.-L.; Zheng, Y.; Ma, J.-A. Org. Chem. Front. 2015, 2, 1468. doi: 10.1039/C5QO00219B
18. [18]
  (a) Fu, D.; Zhang, J.; Cao, S. J. Fluorine Chem. 2013, 156, 170.
  (b) Wei, F.; Zhou, T.; Ma, Y.; Tung, C.-H.; Xu, Z. Org. Lett. 2017, 19, 2098.
  (c) Cheung, K. P. S.; Tsui, G. C. Org. Lett. 2017, 19, 2881.
19. [19]
  (a) Finnegan, W. G.; Henry, R. A.; Lofquist, R. J. Am. Chem. Soc. 1958, 80, 3908.
  (b) Holland, G. F.; Pereira, J. N. J. Med. Chem. 1967, 10, 149.
  (c) Roh, J.; Vávrová, K.; Hrabálek, A. Eur. J. Org. Chem. 2012, 6101.
20. [20]
  (a) Norris, W. P. J. Org. Chem. 1962, 27, 3248.
  (b) Rigby W.; Bailey P. M.; McCleverty J. A.; Maitlis P. M. J. Chem. Soc., Dalton Trans. 1979, 367.
21. [21]
  (a) Uneyama, K. J. Fluorine Chem. 1999, 97, 11.
  (b) Xiao, J.; Zhang, X.; Wang, D.; Yuan, C. J. Fluorine Chem. 1999, 99, 83.
22. [22]
  (a) Armour, D. R.; Chung, K. M. L.; Congreve, M.; Evans, B.; Guntrip, S.; Hubbard, T.; Kay, C.; Middlemiss, D.; Mordaunt, J. E.; Pegg, N. A.; Vinader, M. V.; Ward, P.; Watson, S. P. Bioorg. Med. Chem. Lett. 1996, 6, 1015.
  (b) Hale, J. J.; Mills, S. G.; MacCoss, M.; Finke, P. E.; Cascieri, M. A.; Sadowski, S.; Ber, E.; Chicchi, G. G.; Kurtz, M.; Metzger, J.; Eiermann, G.; Tsou, N. N.; Tattersall, F. D.; Rupniak, N. M. J.; Williams, A. R.; Rycroft, W.; Hargreaves, R.; MacIntyre, D. E. J. Med. Chem. 1998, 41, 4607.
23. [23]
  Chen, Z.; Fan, S.-Q.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2015, 51, 16545. doi: 10.1039/C5CC07324C
24. [24]
  (a) Lebsack, A. D.; Gunzner, J.; Wang, B.; Pracitto, R.; Schaffhauser, H.; Santini, A.; Aiyar, J.; Bezverkov, R.; Munoz, B.; Liu, W.; Venkatraman, S. Bioorg. Med. Chem. Lett. 2004, 14, 2463.
  (b) Desai, A. A. Angew. Chem., Int. Ed. 2011, 50, 1974.
  (c) Aiguadé, J.; Balagué, C.; Carranco, I.; Caturla, F.; Domínguez, M.; Eastwood, P.; Esteve, C.; González, J.; Lumeras, W.; Orellana, A.; Preciado, S.; Roca, R.; Vidal, L.; Vidal, B. Bioorg. Med. Chem. Lett. 2012, 22, 3431.
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Recent Advances in the Synthesis of CF₃-Substituted Triazoles and Tetrazoles