Silver-catalyzed regioselective [3+2] cycloaddition of arene-diazonium salts with 2,2,2-trifluorodiazoethane (CF3CHN2): A facile access to 2-aryl-5-trifluoromethyltetrazoles

Chemical Communications

Volumn 51, Issue 92, 2015, Pages 16545-16548

  Chen, Zhen ^a   Fan, Shuang Qing ^a   Zheng, Yan ^a   Ma, Jun An ^a  

^a TIANJIN UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

2 ARYL 5 TRIFLUOROMETHYLTETRAZOLE DERIVATIVE; 2,2,2 TRIFLUORODIAZOETHANE; ANILINE DERIVATIVE; ARENEDIAZONIUM SALT; FUNCTIONAL GROUP; INORGANIC SALT; PYRAZOLE DERIVATIVE; REAGENT; SILVER; TETRAZOLE DERIVATIVE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CYCLOADDITION; DIAZOTIZATION; ONE POT SYNTHESIS; REACTION ANALYSIS; REACTION OPTIMIZATION;

EID: 84946781114     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c5cc07324c     Document Type: Article

References (40)

1. R. N. Butler, in Comprehensive Heterocyclic Chemistry, ed.; A. R. Katritzky, C. W. Rees, and, E. F. V. Scriven, Pergamon, Oxford, 1996, p. 621
2. R. J. Herr Bioorg. Med. Chem. 2002 10 3379
3. L. V. Myznikov A. Hrabalek G. I. Koldobskii Chem. Heterocycl. Compd. 2007 43 1
4. R. N. Bulter, in Comprehensive Heterocyclic Chemistry, ed.; A. R. Katritzky, and, C. W. Rees, Pergamon, Oxford, 1984, p. 791
5. H. R. Meier and H. Heimgartner, in Methoden der Organischen Chemie, Houben-Weyl, ed.; E. Schumann, Georg Thieme, Stuttgart, 1994, p. 664
6. P. N. Gaponik S. V. Voitekhovich O. A. Ivashkevich Russ. Chem. Rev. 2006 75 507
7. P. Yates D. G. Farnum Tetrahedron Lett. 1960 38 22
8. F. R. Benson Chem. Rev. 1947 41 1
9. S. J. Wittenberger Org. Prep. Proced. Int. 1994 26 499
10. J. Roh K. Vávrová A. Hrabálek Eur. J. Org. Chem. 2012 6101
11. W. Lossen C. L. Lossen Ann. 1891 263 96
12. A. Pinneb Ber. 1894 27 990
13. J. Colman Ber. 1897 30 2010
14. G. Schroeter Ber. 1909 42 2336
15. O. Dimroth G. De Montmollin Ber. 1910 43 2907
16. F. D. Chattaway G. D. Parkbs J. Chem. Soc. 1926 113
17. J. Von Braun W. Keller Ber. Dtsch. Chem. Ges. 1932 65 1677
18. J. V. Braun W. Rudolph Ber. 1941 74 264
19. W. G. Finnegan R. A. Henry R. Lofquist J. Am. Chem. Soc. 1958 80 3908
20. S. Ito Y. Tanaka A. Kakehi Bull. Chem. Soc. Jpn. 1976 49 762
21. P. R. Bernstein E. P. Vacek Synthesis 1987 1133
22. M. Alterman A. Hallberg J. Org. Chem. 2000 65 7984
23. Z. P. Demko K. B. Sharpless J. Org. Chem. 2001 66 7945
24. T. Jin S. Kamijo Y. Yamamoto Tetrahedron Lett. 2004 45 9435
25. B. Gutmann J.-P. Roduit D. Roberge C. O. Kappe Angew. Chem.; Int. Ed. 2010 49 7101
26. Y. Li L.-X. Gao F.-S. Han Chem. Commun. 2012 48 2719
27. T. Onaka H. Umemoto Y. Miki A. Nakamura T. Maegawa J. Org. Chem. 2014 79 6703
28. F. Li J. Nie L. Sun Y. Zheng J.-A. Ma Angew. Chem.; Int. Ed. 2013 52 6255
29. S. Wang L.-J. Yang J.-L. Zeng Y. Zheng J.-A. Ma Org. Chem. Front. 2015 2 10.1039/C5QO00219B
30. C.-B. Liu W. Meng F. Li S. Wang J. Nie J.-A. Ma Angew. Chem.; Int. Ed. 2012 51 6227
31. S. Wang J. Nie Y. Zheng J.-A. Ma Org. Lett. 2014 16 1606
32. H.-Y. Xiong Z.-Y. Yang Z. Chen J.-L. Zeng J. Nie J.-A. Ma Chem.-Eur. J. 2014 20 8325
33. F.-G. Zhang Y. Wei Y.-P. Yi J. Nie J.-A. Ma Org. Lett. 2014 16 3122
34. L. Sun J. Nie Y. Zheng J.-A. Ma J. Fluorine Chem. 2015 174 88
35. A.-J. Cai Y. Zheng J.-A. Ma Chem. Commun. 2015 51 8946
36. M. Naodovic H. Yamamoto Chem. Rev. 2008 108 3132
37. J.-M. Weibel A. Blanc P. Pale Chem. Rev. 2008 108 3149
38. M. Álvarez-Corral M. Muñoz-Dorado I. Rodrííguez-García Chem. Rev. 2008 108 3174
39. T.-F. Liu X.-X. Shao Y.-M. Wu Q.-L. Shen Angew. Chem.; Int. Ed. 2012 51 540
40. X. Wang Y. Xu F.-Y. Mo G.-J. Ji D. Qiu J.-J. Feng Y.-X. Ye S.-N. Zhang Y. Zhang J.-B. Wang J. Am. Chem. Soc. 2013 135 10330