Pure and Applied Chemistry

Pure Appl. Chem., 2012, Vol. 84, No. 3, pp. 553-559

http://dx.doi.org/10.1351/PAC-CON-11-07-04

Published online 2011-09-27

Chlorine-free copper-catalyzed oxidative synthesis of 1,3,4-oxadiazoles with molecular oxygen as the sole oxidant*

References

• 1. C. Glaser. Ber. Dtsch. Chem. Ges. 2, 422 (1969). (http://dx.doi.org/10.1002/cber.186900201183)
• 2. W. Chodkiewicz. Ann. Chim. 2, 819 (1957).
• 3. F. Ullmann. Ann. 332, 38 (1904).
• 4. F. Ullmann, P. Sponagel. Ber. 38, 2211 (1905).
• 5. J. Tsuji. Synthesis 5, 369 (1984). (http://dx.doi.org/10.1055/s-1984-30848)
• 6. K. Sonogashira, Y. Tohda, N. Hagira. Tetrahedron Lett. 50, 4467 (1975). (http://dx.doi.org/10.1016/S0040-4039(00)91094-3)
• 7. J. Li, H. Jiang, L. Jia. Chem. Commun. 23, 2369 (1999). (http://dx.doi.org/10.1039/a908014g)
• 8. L. Jia, H. Jiang, J. Li. Green Chem. 1, 91 (1999). (http://dx.doi.org/10.1039/a901396b)
• 9. H. Jiang, L. Jia, J. Li. Green Chem. 2, 161 (2000). (http://dx.doi.org/10.1039/b002491k)
• 10. L. Jia, H. Jiang, J. Li. Chem. Commun. 23, 985 (1999). (http://dx.doi.org/10.1039/a901935i)
• 11. J. Li, H. Jiang, A. Feng, L. Jia. J. Org. Chem. 64, 5984 (1999). (http://dx.doi.org/10.1021/jo982345u)
• 12. J. Li, H. Jiang, M. Chen. Tetrahedron Lett. 42, 6923 (2001). (http://dx.doi.org/10.1016/S0040-4039(01)01438-1)
• 13. J. Li, H. Jiang, L. Jia. Synth. Commun. 29, 3733 (1999). (http://dx.doi.org/10.1080/00397919908086012)
• 14. J. Li, H. Jiang, M. Chen. Synth. Commun. 31, 199 (2001). (http://dx.doi.org/10.1081/SCC-100000199)
• 15. J. Li, H. Jiang, M. Chen. Synth. Commun. 31, 3131 (2001). (http://dx.doi.org/10.1081/SCC-100105887)
• 16. J. Li, H. Jiang, M. Chen. Chin. J. Chem. 19, 689 (2001). (http://dx.doi.org/10.1002/cjoc.20010190711)
• 17. J. Li, H. Jiang, M. Chen. Green Chem. 3, 137 (2001). (http://dx.doi.org/10.1039/b101732m)
• 18. J. Li, H. Jiang, M. Chen. J. Org. Chem. 66, 3627 (2001). (http://dx.doi.org/10.1021/jo0017382)
• 19. J. Cheng, H. Jiang. Eur. J. Org. Chem. 3, 643 (2004). (http://dx.doi.org/10.1002/ejoc.200300299)
• 20. J. Cheng, J. Li, H. Jiang, X. Ouyang, Q. Zhang. Synth. Commun. 33, 3003 (2003). (http://dx.doi.org/10.1081/SCC-120022474)
• 21. J. Huang, L. Zhou, H. Jiang. Angew. Chem., Int. Ed. 45, 1945 (2006). (http://dx.doi.org/10.1002/anie.200503970)
• 22. H. Jiang, C. Qiao, W. Liu. Chem.—Eur. J. 16, 10968 (2010). (http://dx.doi.org/10.1002/chem.201001318)
• 23. P. Anastas, T. Williamson. Green Chemistry, Oxford University Press, New York (1998).
• 24. Z. Wang, H. Jiang, C. Qi, Y. Wang, H. Liu. Green Chem. 7, 582 (2005). (http://dx.doi.org/10.1039/b505515f)
• 25. Z. Wang, H. Jiang, X. Ouyang, C. Qi, S. Yang. Tetrahedron 62, 9846 (2006). (http://dx.doi.org/10.1016/j.tet.2006.08.041)
• 26. Z. Wang, H. Jiang, C. Qi, Y. Shen, S. Yang, Y. Zeng. Chin. J. Catal. 26, 607 (2007). (http://dx.doi.org/10.1016/S1872-2067(07)60052-7)
• 27. Z. Wang, H. Jiang, C. Qi, Y. Shen, S. Yang. Chin. Chem. Lett. 18, 969 (2007). (http://dx.doi.org/10.1016/j.cclet.2007.05.026)
• 28. H. Jiang, Y. Shen, Z. Wang. Tetrahedron Lett. 48, 7542 (2007). (http://dx.doi.org/10.1016/j.tetlet.2007.08.034)
• 29. H. Jiang, Y. Shen, Z. Wang. Tetrahedron 64, 508 (2008). (http://dx.doi.org/10.1016/j.tet.2007.11.013)
• 30. A. Wang, H. Jiang. J. Am. Chem. Soc. 130, 5030 (2008). (http://dx.doi.org/10.1021/ja8002217)
• 31. A. Wang, H. Jiang, H. Chen. J. Am. Chem. Soc. 131, 3846 (2009). (http://dx.doi.org/10.1021/ja900213d)
• 32. A. Wang, H. Jiang. J. Org. Chem. 75, 2321 (2010). (http://dx.doi.org/10.1021/jo100125q)
• 33. H. Jiang, H. Chen, A. Wang, X. Liu. Chem. Commun. 46, 7259 (2010). (http://dx.doi.org/10.1039/c0cc00841a)
• 34. Y. Shen, H. Jiang, Z. Chen. J. Org. Chem. 75, 1321 (2010). (http://dx.doi.org/10.1021/jo902636g)
• 35. P. Zhou, L. Huang, H. Jiang, A. Wang, X. Li. J. Org. Chem. 75, 8279 (2010). (http://dx.doi.org/10.1021/jo101554r)
• 36. P. Zhou, H. Jiang, L. Huang, X. Li. Chem. Commun. 47, 1003 (2011). (http://dx.doi.org/10.1039/c0cc03723k)
• 37. P. Zhou, M. Zhen, H. Jiang, X. Li, C. Qi. J. Org. Chem. 76, 4759 (2011). (http://dx.doi.org/10.1021/jo200572n)
• 38. L. Huang, H. Jiang, C. Qi, X. Liu. J. Am. Chem. Soc. 132, 17652 (2010). (http://dx.doi.org/10.1021/ja108073k)
• 39. H. Cao, H. Jiang, Y. Yuan, Z. Chen, C. Qi, H. Huang. Chem.—Eur. J. 16, 10553 (2010). (http://dx.doi.org/10.1002/chem.201000807)
• 40. D. C. Palmer (Ed.). Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, John Wiley, Hoboken, NJ (2003).
• 41. D. C. Palmer (Ed.). Oxazoles: Synthesis, Reactions and Spectroscopy, Part B, John Wiley, Hoboken, NJ (2004).
• 42. Z. Jin. Nat. Prod. Rep. 23, 464 (2006). (http://dx.doi.org/10.1039/b502166a)
• 43. V. S. C. Yeh. Tetrahedron 60, 11995 (2004). (http://dx.doi.org/10.1016/j.tet.2004.10.001)
• 44. P. Wipf. Chem. Rev. 95, 2115 (1995). (http://dx.doi.org/10.1021/cr00038a013)
• 45. G. W. Weaver. In Science of Synthesis, Vol. 13, R. C. Storr, T. L. Gilchrist (Eds.), pp. 219–251, Thieme, Stuttgart (2004).
• 46. J. Hill. In Comprehensive Heterocyclic Chemistry II, Vol. 4, R. C. Storr (Ed.), pp. 267–287, 905–1006, Pergamon, Oxford (1996).
• 47. Q. Chen, X. L. Zhu, L. L. Jiang, Z. M. Liu, G. F. Yang. Eur. J. Med. Chem. 43, 595 (2008). (http://dx.doi.org/10.1016/j.ejmech.2007.04.021)
• 48. R. B. Shankar, R. G. Pews. J. Heterocycl. Chem. 30, 169 (1993). (http://dx.doi.org/10.1002/jhet.5570300130)
• 49. F. A. Omar, N. M. Mahfouz, M. A. Rahman. Eur J. Med. Chem. 31, 819 (1996). (http://dx.doi.org/10.1016/0223-5234(96)83976-6)
• 50. S. Perez, B. Lasheras, C. Oset, A. Carmen. J. Heterocycl. Chem. 34, 1527 (1997). (http://dx.doi.org/10.1002/jhet.5570340523)
• 51. P. K. Hegde, A. V. Adhikari, M. G. Manjunatha, C. S. S. Sandeep, P. Reji. Synth. Met. 159, 1099 (2009). (http://dx.doi.org/10.1016/j.synthmet.2009.01.034)
• 52. C. C. Chiang, H. C. Chen, C. Lee, M. Leung, K. R. Lin, K. H. Hsieh. Chem. Mater. 20, 540 (2008). (http://dx.doi.org/10.1021/cm702217u)
• 53. C. J. Qin, A. L. Gavrilova, B. Bosnich. Inorg. Chem. 40, 1386 (2001). (http://dx.doi.org/10.1021/ic0106625)
• 54. K. C. Chiang, F. F. Wong, C. H. Hung, Y. Y. Huang, P. W. Chang, Y. M. Liao, S. K. Linb. J. Heterocycl. Chem. 46, 111 (2006). (http://dx.doi.org/10.1002/jhet.21)
• 55. C. Dobrota, C. C. Paraschivescu, I. Dumitru, M. Matache, I. Baciu, L. L. Ruta. Tetrahedron Lett. 50, 1886 (2009). (http://dx.doi.org/10.1016/j.tetlet.2009.02.054)
• 56. A. Husain, A. Ahmad, M. M. Alam, Mohd Ajmal, P. Ahuja. Eur. J. Med. Chem. 44, 3798 (2009). (http://dx.doi.org/10.1016/j.ejmech.2009.04.009)
• 57. S. Rostamizadeh, S. A. G. Housaini. Tetrahedron Lett. 45, 8753 (2004). (http://dx.doi.org/10.1016/j.tetlet.2004.09.095)
• 58. For a discussion of mechanisms involving Cu(III) intermediates, see: S. V. Ley, A. W. Thomas. Angew. Chem., Int. Ed. 42, 5400 (2003). (http://dx.doi.org/10.1002/anie.200300594)
• 59. For a report suggesting a Cu metallacycle as intermediate, see: K. Yamada, T. Kubo, H. Tokuyama, T. Fukuyama. Synlett 2, 231 (2002). (http://dx.doi.org/10.1055/s-2002-19782)