Efficient synthesis of 2,5-disubstituted tetrazoles via the Cu2O-catalyzed aerobic oxidative direct cross-coupling of N-H free tetrazoles with boronic acids

Chemical Communications

Volumn 48, Issue 21, 2012, Pages 2719-2721

  Li, Yu ^a,b   Gao, Lian Xun ^a   Han, Fu She ^a,c  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c State Key Laboratory of Fine Chemicals   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ACID DERIVATIVE; TETRAZOLE DERIVATIVE;

AEROBIC METABOLISM; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; OXIDATION; STEREOCHEMISTRY; SYNTHESIS; TEMPERATURE;

EID: 84863171321     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c2cc17894j     Document Type: Article

References (26)

1. R. N. Butler, in Comprehensive Heterocyclic Chemistry, ed. A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergammon, Oxford, UK, 1996, vol. 4
2. A. D. Bond, A. Fleming, F. Kelleher, J. McGinley, V. Prajapati, Tetrahedron, 2006, 62, 9577
3. R. J. Herr, Bioorg. Med. Chem., 2002, 10, 3379
4. M. A. Hiskey, D. Chavez, D. L. Naud, S. F. Son, H. L. Berghout, C. A. Bolme, Proc. Int. Pyrotech. Semin., 2000, 27, 3
5. A. S. Gundugola, K. L. Chandra, E. M. Perchellet, A. M. Waters, J.-P. H. Perchellet, S. Rayat, Bioorg. Med. Chem. Lett., 2010, 20, 3920
6. P. Srihari, P. Dutta, R. S. Rao, J. S. Yadav, S. Chandrasekhar, P. Thombare, J. Mohapatra, A. Chatterjee, M. R. Jain, Bioorg. Med. Chem. Lett., 2009, 19, 5569
7. Y. Wang, W. Song, W. J. Hu, Q. Lin, Angew. Chem., Int. Ed., 2009, 48, 5330
8. W. Song, Y. Wang, J. Qu, M. M. Madden, Q. Lin, Angew. Chem., Int. Ed., 2008, 47, 2832
9. W. Song, Y. Wang, J. Qu, Q. Lin, J. Am. Chem. Soc., 2008, 130, 9654
10. Y. Wang, W. J. Hu, W. Song, R. K. V. Lim, Q. Lin, Org. Lett., 2008, 10, 3725
11. F. Chen, C. Qin, Y. Cui, N. Jiao, Angew. Chem., Int. Ed., 2011, 50, 11487
12. Z. P. Demko, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2110
13. Z. P. Demko, K. B. Sharpless, Angew. Chem., Int. Ed., 2002, 41, 2113
14. L. E. Kaim, L. Grimaud, P. Patil, Org. Lett., 2011, 13, 1261
15. Q. Tang, R. Gianatassio, Tetrahedron Lett., 2010, 51, 3473
16. Y. Wang, Q. Lin, Org. Lett., 2009, 11, 3570
17. S. Ito, Y. Tanaka, A. Kakehi, K. Kondo, Bull. Chem. Soc. Jpn., 1976, 49, 1920
18. P. Y. S. Lam, C. G. Clark, S. Saubern, J. Adams, M. P. Winters, D. M. T. Chan, A. Combs, Tetrahedron Lett., 1998, 39, 2941
19. I. P. Beletskaya, D. V. Davydov, M. S. Gorovoy, Tetrahedron Lett., 2002, 43, 6221
20. D. V. Davydov, I. P. Beletskaya, B. B. Semenov, Y. I. Smushkevich, Tetrahedron Lett., 2002, 43, 6217
21. Y. Li, L.-X. Gao, F.-S. Han, Chem.-Eur. J., 2010, 16, 7969
22. T. Kinzel, Y. Zhang, S. L. Buchwald, J. Am. Chem. Soc., 2010, 132, 14073
23. G. C. H. Chiang, T. Olsson, Org. Lett., 2004, 6, 3079
24. C. A. Bernhart, P. M. Perreaut, B. P. Ferrari, Y. A. Muneaux, J.-L. A. Assens, J. Clément, F. Haudricourt, C. F. Muneaux, J. E. Taillades, M.-A. Vignal, J. Gougat, P. R. Guiraudou, C. A. Lacour, A. Roccon, C. F. Cazaubon, J.-C. Brelière, G. L. Fur, D. Nisato, J. Med. Chem., 1993, 36, 3371
25. P. Bühlmayer, P. Furet, L. Criscione, M. de Gasparo, S. Whitebread, T. Schmidlin, R. Lattmann, J. Wood, Bioorg. Med. Chem. Lett., 1994, 4, 29
26. A. E. King, T. C. Brunold, S. S. Stahl, J. Am. Chem. Soc., 2009, 131, 5044