Chlorine-free is not only one of the new concepts of green chemistry, but also a problematical task for chemical processes in industrial utility. During the past several decades, we devoted ourselves to the study of chlorine-free organic synthesis. Herein, we describe an efficient chlorine-free copper-catalyzed oxidative approach providing 1,3,4-oxadiazoles in good yields from readily available starting materials. This transformation requires only a green and inexpensive reagent to afford the structurally useful motifs, and has a broad functional groups tolerance.
References
1 10.1002/cber.186900201183, C. Glaser. Ber. Dtsch. Chem. Ges.2, 422 (1969).Search in Google Scholar
2 W. Chodkiewicz. Ann. Chim.2, 819 (1957).10.1136/bmj.2.5048.819Search in Google Scholar
3 F. Ullmann. Ann.332, 38 (1904).10.1002/jlac.19043320104Search in Google Scholar
4 F. Ullmann, P. Sponagel. Ber.38, 2211 (1905).Search in Google Scholar
5 10.1055/s-1984-30848, J. Tsuji. Synthesis5, 369 (1984).Search in Google Scholar
6 10.1016/S0040-4039(00)91094-3, K. Sonogashira, Y. Tohda, N. Hagira. Tetrahedron Lett.50, 4467 (1975).Search in Google Scholar
7 10.1039/a908014g, J. Li, H. Jiang, L. Jia. Chem. Commun.23, 2369 (1999).Search in Google Scholar
8 10.1039/a901396b, L. Jia, H. Jiang, J. Li. Green Chem.1, 91 (1999).Search in Google Scholar
9 10.1039/b002491k, H. Jiang, L. Jia, J. Li. Green Chem.2, 161 (2000).Search in Google Scholar
10 10.1039/a901935i, L. Jia, H. Jiang, J. Li. Chem. Commun.23, 985 (1999).Search in Google Scholar
11 10.1021/jo982345u, J. Li, H. Jiang, A. Feng, L. Jia. J. Org. Chem.64, 5984 (1999).Search in Google Scholar
12 10.1016/S0040-4039(01)01438-1, J. Li, H. Jiang, M. Chen. Tetrahedron Lett.42, 6923 (2001).Search in Google Scholar
13 10.1080/00397919908086012, J. Li, H. Jiang, L. Jia. Synth. Commun.29, 3733 (1999).Search in Google Scholar
14 10.1081/SCC-100000199, J. Li, H. Jiang, M. Chen. Synth. Commun.31, 199 (2001).Search in Google Scholar
15 10.1081/SCC-100105887, J. Li, H. Jiang, M. Chen. Synth. Commun.31, 3131 (2001).Search in Google Scholar
16 10.1002/cjoc.20010190711, J. Li, H. Jiang, M. Chen. Chin. J. Chem.19, 689 (2001).Search in Google Scholar
17 10.1039/b101732m, J. Li, H. Jiang, M. Chen. Green Chem.3, 137 (2001).Search in Google Scholar
18 10.1021/jo0017382, J. Li, H. Jiang, M. Chen. J. Org. Chem.66, 3627 (2001).Search in Google Scholar PubMed
19 10.1002/ejoc.200300299, J. Cheng, H. Jiang. Eur. J. Org. Chem.3, 643 (2004).Search in Google Scholar
20 10.1081/SCC-120022474, J. Cheng, J. Li, H. Jiang, X. Ouyang, Q. Zhang. Synth. Commun.33, 3003 (2003).Search in Google Scholar
21 10.1002/anie.200503970, J. Huang, L. Zhou, H. Jiang. Angew. Chem., Int. Ed.45, 1945 (2006).Search in Google Scholar PubMed
22 10.1002/chem.201001318, H. Jiang, C. Qiao, W. Liu. Chem.—Eur. J.16, 10968 (2010).Search in Google Scholar
23 P. Anastas, T. Williamson. Green Chemistry, Oxford University Press, New York (1998).Search in Google Scholar
24 10.1039/b505515f, Z. Wang, H. Jiang, C. Qi, Y. Wang, H. Liu. Green Chem.7, 582 (2005).Search in Google Scholar
25 10.1016/j.tet.2006.08.041, Z. Wang, H. Jiang, X. Ouyang, C. Qi, S. Yang. Tetrahedron62, 9846 (2006).Search in Google Scholar
26 10.1016/S1872-2067(07)60052-7, Z. Wang, H. Jiang, C. Qi, Y. Shen, S. Yang, Y. Zeng. Chin. J. Catal.26, 607 (2007).Search in Google Scholar
27 10.1016/j.cclet.2007.05.026, Z. Wang, H. Jiang, C. Qi, Y. Shen, S. Yang. Chin. Chem. Lett.18, 969 (2007).Search in Google Scholar
28 10.1016/j.tetlet.2007.08.034, H. Jiang, Y. Shen, Z. Wang. Tetrahedron Lett.48, 7542 (2007).Search in Google Scholar
29 10.1016/j.tet.2007.11.013, H. Jiang, Y. Shen, Z. Wang. Tetrahedron64, 508 (2008).Search in Google Scholar
30 10.1021/ja8002217, A. Wang, H. Jiang. J. Am. Chem. Soc.130, 5030 (2008).Search in Google Scholar PubMed
31 10.1021/ja900213d, A. Wang, H. Jiang, H. Chen. J. Am. Chem. Soc.131, 3846 (2009).Search in Google Scholar PubMed
32 10.1021/jo100125q, A. Wang, H. Jiang. J. Org. Chem.75, 2321 (2010).Search in Google Scholar PubMed
33 10.1039/c0cc00841a, H. Jiang, H. Chen, A. Wang, X. Liu. Chem. Commun.46, 7259 (2010).Search in Google Scholar PubMed
34 10.1021/jo902636g, Y. Shen, H. Jiang, Z. Chen. J. Org. Chem.75, 1321 (2010).Search in Google Scholar PubMed
35 10.1021/jo101554r, P. Zhou, L. Huang, H. Jiang, A. Wang, X. Li. J. Org. Chem.75, 8279 (2010).Search in Google Scholar PubMed
36 10.1039/c0cc03723k, P. Zhou, H. Jiang, L. Huang, X. Li. Chem. Commun.47, 1003 (2011).Search in Google Scholar PubMed
37 10.1021/jo200572n, P. Zhou, M. Zhen, H. Jiang, X. Li, C. Qi. J. Org. Chem.76, 4759 (2011).Search in Google Scholar PubMed
38 10.1021/ja108073k, L. Huang, H. Jiang, C. Qi, X. Liu. J. Am. Chem. Soc.132, 17652 (2010).Search in Google Scholar PubMed
39 10.1002/chem.201000807, H. Cao, H. Jiang, Y. Yuan, Z. Chen, C. Qi, H. Huang. Chem.—Eur. J.16, 10553 (2010).Search in Google Scholar PubMed
40 D. C. Palmer (Ed.). Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, John Wiley, Hoboken, NJ (2003).Search in Google Scholar
41 D. C. Palmer (Ed.). Oxazoles: Synthesis, Reactions and Spectroscopy, Part B, John Wiley, Hoboken, NJ (2004).Search in Google Scholar
42 10.1039/b502166a, Z. Jin. Nat. Prod. Rep.23, 464 (2006).Search in Google Scholar PubMed
43 10.1016/j.tet.2004.10.001, V. S. C. Yeh. Tetrahedron60, 11995 (2004).Search in Google Scholar
44 10.1021/cr00038a013, P. Wipf. Chem. Rev.95, 2115 (1995).Search in Google Scholar
45 G. W. Weaver. In Science of Synthesis, Vol. 13, R. C. Storr, T. L. Gilchrist (Eds.), pp. 219–251, Thieme, Stuttgart (2004).Search in Google Scholar
46 J. Hill. In Comprehensive Heterocyclic Chemistry II, Vol. 4, R. C. Storr (Ed.), pp. 267–287, 905–1006, Pergamon, Oxford (1996).10.1016/B978-008096518-5.00084-8Search in Google Scholar
47 10.1016/j.ejmech.2007.04.021, Q. Chen, X. L. Zhu, L. L. Jiang, Z. M. Liu, G. F. Yang. Eur. J. Med. Chem.43, 595 (2008).Search in Google Scholar
48 10.1002/jhet.5570300130, R. B. Shankar, R. G. Pews. J. Heterocycl. Chem.30, 169 (1993).Search in Google Scholar
49 10.1016/0223-5234(96)83976-6, F. A. Omar, N. M. Mahfouz, M. A. Rahman. Eur J. Med. Chem.31, 819 (1996).Search in Google Scholar
50 10.1002/jhet.5570340523, S. Perez, B. Lasheras, C. Oset, A. Carmen. J. Heterocycl. Chem.34, 1527 (1997).Search in Google Scholar
51 10.1016/j.synthmet.2009.01.034, P. K. Hegde, A. V. Adhikari, M. G. Manjunatha, C. S. S. Sandeep, P. Reji. Synth. Met.159, 1099 (2009).Search in Google Scholar
52 10.1021/cm702217u, C. C. Chiang, H. C. Chen, C. Lee, M. Leung, K. R. Lin, K. H. Hsieh. Chem. Mater.20, 540 (2008).Search in Google Scholar
53 10.1021/ic0106625, C. J. Qin, A. L. Gavrilova, B. Bosnich. Inorg. Chem.40, 1386 (2001).Search in Google Scholar PubMed
54 10.1002/jhet.21, 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).Search in Google Scholar
55 10.1016/j.tetlet.2009.02.054, C. Dobrota, C. C. Paraschivescu, I. Dumitru, M. Matache, I. Baciu, L. L. Ruta. Tetrahedron Lett.50, 1886 (2009).Search in Google Scholar
56 10.1016/j.ejmech.2009.04.009, A. Husain, A. Ahmad, M. M. Alam, Mohd Ajmal, P. Ahuja. Eur. J. Med. Chem.44, 3798 (2009).Search in Google Scholar PubMed
57 10.1016/j.tetlet.2004.09.095, S. Rostamizadeh, S. A. G. Housaini. Tetrahedron Lett.45, 8753 (2004).Search in Google Scholar
58 10.1002/anie.200300594, For a discussion of mechanisms involving Cu(III) intermediates, see: S. V. Ley, A. W. Thomas. Angew. Chem., Int. Ed.42, 5400 (2003).Search in Google Scholar PubMed
59 10.1055/s-2002-19782, For a report suggesting a Cu metallacycle as intermediate, see: K. Yamada, T. Kubo, H. Tokuyama, T. Fukuyama. Synlett2, 231 (2002).Search in Google Scholar
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