Source: http://sioc-journal.cn/Jwk_yjhx/CN/abstract/abstract346826.shtml
Timestamp: 2019-04-25 09:09:08+00:00

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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.
张发光, 彭星, 马军安. 三氟甲基三氮唑及四氮唑化合物的合成研究进展[J]. 有机化学, 2019, 39(1): 109-116.	Zhang Faguang, Peng Xing, Ma Jun'an. Recent Advances in the Synthesis of CF3-Substituted Triazoles and Tetrazoles. Chin. J. Org. Chem., 2019, 39(1): 109-116.
 (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.
 (a) O'Hagan, D. Chem. Soc. Rev. 2008, 37, 308.
(b) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320.
(c) Ma, J.-A.; Cahard, D. Chem. Rev. 2008, 108, PR1.
(d) Nie, J.; Guo, H.-C.; Cahard, D.; Ma, J.-A. Chem. Rev. 2011, 111, 455.
(f) Neumann, C. N.; Ritter, T. Angew. Chem., Int. Ed. 2015, 54, 3216.
(g) Yang, X.; Wu, T.; Phipps, R. J.; Toste, F. D. Chem. Rev. 2015, 115, 826.
(h) Zhang, Y.; Li, Z.; Song, H.; Wang, B. Chin. J. Chem. 2018, 36, 635.
 (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.
 (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.
 (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.
 (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.
 Wei, J.; Chen, J.; Xu, J.; Cao, L.; Deng, H.; Sheng, W.; Zhang, H.; Cao, W. J. Fluorine Chem. 2012, 133, 146.
 Funabiki, K.; Noma, N.; Kuzuya, G.; Matsui, M.; Shibata, K. J. Chem. Res. 1999, 300.
 Sibgatulin, D. A.; Bezdudny, A. V.; Mykhailiuk, P. K.; Voievoda, N. M.; Kondratov, I. S.; Volochnyuk, D. M.; Tolmachev, A. A. Synthesis 2010, 1075.
 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.
 Chen, M.; Wang, X.-F.; Wang, S.-S.; Feng, Y.-X.; Chen, F.; Yang, C.-L. J. Fluorine Chem. 2012, 135, 323.
 Peng, W.; Zhu, S. Tetrahedron 2003, 59, 4395.
 (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.
 (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.
 (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.
 (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.
 Wang, S.; Yang, L.-J.; Zeng, J.-L.; Zheng, Y.; Ma, J.-A. Org. Chem. Front. 2015, 2, 1468.
 (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.
 (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.
 (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.
 (a) Uneyama, K. J. Fluorine Chem. 1999, 97, 11.
(b) Xiao, J.; Zhang, X.; Wang, D.; Yuan, C. J. Fluorine Chem. 1999, 99, 83.
 (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.
 Chen, Z.; Fan, S.-Q.; Zheng, Y.; Ma, J.-A. Chem. Commun. 2015, 51, 16545.
 (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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