Synthesis of 3-trifluoromethylpyrazoles via trifluoromethylation/cyclization of α,β-alkynic hydrazones using a hypervalent iodine reagent

Chemical Communications

Volumn 50, Issue 33, 2014, Pages 4361-4363

  Ji, Guojing ^a,b   Wang, Xi ^a   Zhang, Songnan ^a   Xu, Yan ^a   Ye, Yuxuan ^a   Li, Ming ^b   Zhang, Yan ^a   Wang, Jianbo ^a  

^a PEKING UNIVERSITY   (China)

^b QINGDAO UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

HYDRAZONE DERIVATIVE; IODINE; PYRAZOLE DERIVATIVE; ALKYNE DERIVATIVE; FLUORINE DERIVATIVE; REAGENT; TRANSITION ELEMENT;

CATALYSIS; CHEMISTRY; CYCLIZATION; METHYLATION; SYNTHESIS; ARTICLE; BIOTRANSFORMATION; CHEMICAL REACTION; QUANTUM YIELD; REACTION ANALYSIS; TRIFLUOROMETHYLATION;

CATALYSIS; CYCLIZATION; HYDRAZONES; IODINE; METHYLATION; PYRAZOLES;

EID: 84897125656     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c4cc01280a     Document Type: Article

References (31)

1. K. Müller, C. Faeh, F. Diederich, Science, 2007, 317, 1881
2. G. K. S. Prakash, A. K. Yudin, Chem. Rev., 1997, 97, 757
3. M. Shimizu, T. Hiyama, Angew. Chem., Int. Ed., 2005, 44, 214
4. M. Schlosser, Angew. Chem., Int. Ed., 2006, 45, 5432
5. J. A. Ma, D. Cahard, J. Fluorine Chem., 2007, 128, 975
6. J. A. Ma, D. Cahard, Chem. Rev., 2008, 108, PR1
7. O. A. Tomashenko, V. V. Grushin, Chem. Rev., 2011, 111, 4475
8. T. Besset, C. Schneider, D. Cahard, Angew. Chem., Int. Ed., 2012, 51, 5048
9. Y. Macé, E. Magnier, Eur. J. Org. Chem., 2012, 2479
10. N. Shibata, A. Matsnev, D. Cahard, Beilstein J. Org. Chem., 2010, 6, 65
11. X. F. Wu, H. Neumann, M. Beller, Chem.-Asian J., 2012, 7, 1744
12. A. Studer, Angew. Chem., Int. Ed., 2012, 51, 8950
13. T. Liang, C. N. Neumann, T. Ritter, Angew. Chem., Int. Ed., 2013, 52, 8214
14. S. Fustero, M. Sánchez-Roselló, P. Barrio, A. Simón-Fuentes, Chem. Rev., 2011, 111, 6984
15. T. D. Penning, J. J. Talley, S. R. Bertenshaw, J. S. Carter, P. W. Collins, S. Doctor, M. J. Greveto, L. F. Lee, J. W. Malecha, J. M. Miyashiro, R. S. Rogers, D. J. Rogier, S. S. Yu, G. D. Anderson, E. G. Burton, S. A. Gregory, C. M. Icoboldt, W. E. Perkus, K. Seibert, A. W. Veenhuizen, Y. Y. Zhang, P. C. Isakson, J. Med. Chem., 1997, 40, 1347
16. S. R. Cox, S. P. Lesman, J. F. Boucher, M. J. Krautmann, B. D. Hummel, M. Savides, S. Marsh, A. Fielder, M. R. Stegemann, J. Vet. Pharmacol. Ther., 2010, 33, 461
17. E. Lee, M. K. Choi, H. J. Youk, C. H. Kim, I. C. Han, B. C. Yoo, M. K. Lee, S. J. Lim, J. Cancer Res. Clin. Oncol., 2006, 132, 232
18. V. Montoya, J. Pons, J. García-Antón, X. Solans, M. Font-Bardia, J. Ros, J. Fluorine Chem., 2007, 128, 1007
19. S. Fustero, R. Román, J. F. Sanz-Cervera, A. Simón-Fuentes, A. C. Cuñat, S. Villanova, M. Murguía, J. Org. Chem., 2008, 73, 3523
20. H. Dai, Y.-Q. Li, D. Du, X. Qin, X. Zhang, H.-B. Yu, J.-X. Fang, J. Agric. Food Chem., 2008, 56, 10805
21. X. Yang, S. Shui, X. Chen, H. He, F. Wu, J. Fluorine Chem., 2010, 131, 426
22. R. Fields, J. P. Tomlinson, J. Fluorine Chem., 1979, 13, 147
23. F. Li, J. Nie, L. Sun, Y. Zheng, J.-A. Ma, Angew. Chem., Int. Ed., 2013, 52, 6255
24. M. Zora, A. Kivrak, C. Yazici, J. Org. Chem., 2011, 76, 6726
25. J. Qian, Y. Liu, J. Zhu, B. Jiang, Z. Xu, Org. Lett., 2011, 13, 4220
26. R. Koller, K. Stanek, D. Stolz, R. Aardoom, K. Niedermann, A. Togni, Angew. Chem., Int. Ed., 2009, 48, 4332
27. N. Santschi, A. Togni, J. Org. Chem., 2011, 76, 4189
28. K. Niedermann, N. Früh, E. Vinogradova, M. S. Wiehn, A. Moreno, A. Togni, Angew. Chem., Int. Ed., 2011, 50, 1059
29. K. Niedermann, N. Früh, R. Senn, B. Czarniecki, R. Verel, A. Togni, Angew. Chem., Int. Ed., 2012, 51, 6511
30. A. T. Parsons, S. L. Buchwald, Angew. Chem., Int. Ed., 2011, 50, 9120
31. X. Wang, Y. Ye, S. Zhang, J. Feng, Y. Xu, Y. Zhang, J. Wang, J. Am. Chem. Soc., 2011, 133, 16410