Copper-catalyzed synthesis of aryl azides and 1-aryl-1,2,3-triazoles from boronic acids

Tetrahedron Letters

Volumn 48, Issue 20, 2007, Pages 3525-3529

  Tao, Chuan Zhou ^a   Cui, Xin ^a   Li, Juan ^a   Liu, Ai Xiang ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; AZIDE; BORONIC ACID DERIVATIVE; COPPER;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CROSS COUPLING REACTION; SYNTHESIS;

EID: 34247132202     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.03.107     Document Type: Article

References (42)

1. For a review, see:. Scriven E.F.V., and Turnbull K. Chem. Rev. 88 (1988) 297
2. For recent studies on aryl azides, see:. Ragaina F., Penoni A., Gallo E., Tollari S., Gotti C.L., Lapadula M., Mangioni E., and Cenini S. Chem. Eur. J. 9 (2003) 249
3. Molteni G., and Ponti A. Chem. Eur. J. 9 (2003) 2770
4. Brown S.D., Betley T.A., and Peters J.C. J. Am. Chem. Soc. 125 (2003) 322
5. Avemaria F., Zimmermann V., and Braese S. Synlett (2004) 1163
6. Lu B., Xie X.-A., Zhu J.-D., and Ma D.-W. Chin. J. Chem. 23 (2005) 1637
7. Lucas R.L., Powell D.R., and Borovik A.S. J. Am. Chem. Soc. 127 (2005) 11596
8. Bart S.C., Lobkovsky E., Bill E., and Chirik P.J. J. Am. Chem. Soc. 128 (2006) 5302
9. For recent studies on vinyl azides, see:. Timen A.S., Risberg E., and Somfai P. Tetrahedron Lett. 44 (2003) 5339
10. Singh P.N.D., Carter C.L., and Gudmundsdottir A.D. Tetrahedron Lett. 44 (2003) 6763
11. Shaikh A.L., Puranik V.G., and Deshmukh A.R. Tetrahedron Lett. 47 (2006) 5993
12. Gartner C.A. Curr. Med. Chem. 10 (2003) 671
13. Peng Q., Qu F.Q., Xia Y., Zhou J.H., Wu Q.Y., and Peng L. Chin. Chem. Lett. 16 (2005) 349
14. Kuse M., Doi I., Kondo N., Kageyama Y., and Isobe M. Tetrahedron 61 (2005) 5754
15. Han S.-Y., Park S.-S., Lee W.G., Min Y.K., and Kim B.T. Bioorg. Med. Chem. Lett. 16 (2006) 129
16. Rizk M.S., Shi X., and Platz M.S. Biochemistry 45 (2006) 543
17. Liu Q., and Tor Y. Org. Lett. 5 (2003) 2571
18. Das J., Patil S.N., Awasthi R., Narasimhulu C.P., and Trehan S. Synthesis (2005) 1801
19. Zhu W., and Ma D. Chem. Commun. (2004) 888
20. Feldman A.K., Colasson B., and Fokin V.V. Org. Lett. 6 (2004) 3897
21. Andersen J., Bolvig S., and Liang X. Synlett (2005) 2941
22. Zhao Y.-B., Yan Z.-Y., and Liang Y.-M. Tetrahedron Lett. 47 (2006) 1545
23. Recent reviews:. Kolb H.C., Finn M.G., and Sharpless K.b. Angew. Chem., Int. Ed. 40 (2001) 2004
24. Kolb H.C., and Sharpless K.B. Drug Discovery Today 8 (2003) 1128
25. Nayyaw A., and Jain R. Curr. Med. Chem. 12 (2005) 1873
26. Bock V.D., Hiemstra H., and van Maarseveen J.H. Eur. J. Org. Chem. (2005) 51
27. Dong W.-L., Zhao W.-G., Li Y.-X., Liu Z.-X., and Li Z.-M. Chin. J. Org. Chem. 26 (2006) 271
28. For a very interesting application of organic azides in drug discovery, see:. Whiting M., Muldoon J., Lin Y.-C., Silverman S.m., Lindstrom W., Olson A.J., Kolb H.C., Finn M.G., Sharpless K.B., Elder J.H., and Fokin V.V. Angew. Chem., Int. Ed. 45 (2006) 1435
29. Lam P.Y.S., Clark C.G., Saubern S., Adams J., Winters M.P., Chan D.M.T., and Combs A. Tetrahedron Lett. 39 (1998) 2941
30. Very recent examples:. Lan J.-B., Chen L., Yu X.-Q., You J.-S., and Xie R.-G. Chem. Commun. (2004) 188
31. Beaulieu C., Guay D., Wang Z., and Evans D.A. Tetrahedron Lett. 45 (2004) 3233
32. Lan J.-B., Zhang G.-L., Yu X.-Q., You J.-S., Chen L., Yan M., and Xie R.-G. Synlett (2004) 1095
33. Moessner C., and Bolm C. Org. Lett. 7 (2005) 2667
34. Strouse J.J., Jeselnik M., Tapaha F., Jonsson C.B., Parker W.B., and Arterburn J.B. Tetrahedron Lett. 46 (2005) 5699
35. Wang L., Wang M., and Huang F. Synlett (2005) 2007
36. Dai Q., Ran C., and Harvey R.G. Tetrahedron 62 (2006) 1764
37. Zhang L.-Y., and Wang L. Chin. J. Chem. 24 (2006) 1605
38. Singh B.K., Appukkutta P., Claerhout S., Parmar V.S., and Van der Eycken E. Org. Lett. 8 (2006) 1863
39. Kantam M.L., Venkanna G.T., Sridhar C., Sreedhar B., and Choudary B.M. J. Org. Chem. 71 (2006) 9522
40. 4 (0.1 mmol, 16 mg) were placed in an oven-dried round-bottomed flask. Subsequently methanol (3 mL) and boronic acids (1.0 mmol) were added. The reaction mixture was stirred vigorously at room temperature for a certain time (monitored by TLC analysis). The resulting mixture was concentrated in vacuo, and the residue was extracted with petroleum ether or purified by a pad of silicon gel to give the desired aryl or vinyl azide.
41. 4 (0.1 mmol, 16 mg), and boronic acids (1.0 mmol) were reacted in methanol (3 mL) as described above for 5-14 h. Then water (3 mL), sodium ascorbate (0.5 mmol), and phenylacetylene (1.1 mmol) were added into the reaction mixture. The resulting mixture was stirred vigorously at room temperature for 2-4 h (as monitored by TLC analysis). Some precipitate was formed and collected by a simple filtration. After the precipitate was washed with water (3 × 25 mL), it was dried in air or further purified by flash chromatography to afford the pure product.
42. Chao J.-P., Wu W.-Q., Luo X.-D., and Ling Y.-Z. Chin. J. Org. Chem. 26 (2006) 1004