Cu(I)-catalyzed reaction of diazo compounds with terminal alkynes: A direct synthesis of trisubstituted furans

Tetrahedron

Volumn 70, Issue 39, 2014, Pages 6957-6962

  Hossain, Mohammad Lokman ^a   Ye, Fei ^a   Zhang, Yan ^a   Wang, Jianbo ^a,b  

^a PEKING UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Alkyne; Copper catalyst; Diazo compounds; Furan synthesis; Pyrrole synthesis

Indexed keywords

ALKYNE; BUTYRIC ACID; CUPROUS ION; FURAN DERIVATIVE; PYRROLE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CONTROLLED STUDY; CYCLIZATION; ELECTRON; PRIORITY JOURNAL; SYNTHESIS;

EID: 84923137489     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2014.07.086     Document Type: Article

References (39)

1. (a) Hou, X. L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Gilchrist, T. L., Eds.; Pergamon: Oxford, UK, 2003; Vol. 15, p 167;
2. (b) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, NY, 1983; Vol. 31, p 237;
3. (c) Sargent, M. V.; Dean, F. M. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon: Oxford, UK, 1984; Vol. 3, p 599.
4. (a) Lipshutz, B. H. Chem. Rev. 1986, 86, 795;
5. (b) Dean, F. M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic: New York, NY, 1982; Vol. 30, p 167;
6. (c) Dean, F. M.; Sargent, M. V. In Comprehensive Heterocyclic Chemistry; Bird, C. W., Cheeseman, G. W. H., Eds.; Pergamon: New York, NY, 1984; Vol. 4; Part 3, p 531.
7. For reviews on the synthesis of furan derivatives: (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y. T.; Wong, H. N. C. Tetrahedron 1998, 54, 1955;
8. (b) Kirsch, S. F. Org. Biomol. Chem. 2006, 4, 2076;
9. (c) Beay, B. A. Chem. Soc. Rev. 1999, 28, 209;
10. (d) Cacchi, S. J. Organomet. Chem. 1999, 576, 42;
11. (e) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 850;
12. (f) Benassi, R. In Comprehensive Heterocyclic Chemistry II; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, UK, 1996; Vol. 2, p 259;
13. (g) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, UK, 1991.
14. For reviews on a-diazocarbonyl compounds, see: (a) Doyle, M. P.; McKervey, M. A.; Ye, T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds; Wiley: New York, NY, 1998;
15. (b) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091;
16. (c) Zhang Z., Wang J. Tetrahedron 2008, 64, 6577.
17. (a) Davies, H. M. L.; Romines, K. R. Tetrahedron 1988, 44, 3343;
18. (b) Davies, H. M. L.; Cantrell, W. R., Jr.; Romines, K. R.; Baum, J. S. Org. Synth., Coll. Vol. 1998, 9, 422;
19. (c) Briones, J. F.; Davies, H. M. L. Tetrahedron 2011, 67, 4313.
20. (a) Kinder, F. R.; Padwa, A. Tetrahedron Lett. 1990, 31, 6835;
21. (b) Padwa, A.; Chiacchio, U.; Gareau, Y.; Kassir, J. M.; Krumpe, K. E.; Schoffstall, A. M. J. Org. Chem. 1990, 55, 414;
22. (c) Padwa, A.; Krumpe, K. E.; Gareau, Y.; Chiacchio, U. J. Org. Chem. 1991, 56, 2523;
23. (d) Padwa, A.; Krumpe, K. E.; Kassir, J.M. J. Org. Chem.1992, 57, 4940;
24. (e) Pirrung, M. C.; Zhang, J.; Morehead, A. T. Tetrahedron Lett. 1994, 35, 6229;
25. (f) Pang, W.; Zhu, S.; Xin, Y.; Jiang, H.; Zhu, S. Tetrahedron 2010, 66, 1261.
26. Cui, X.; Xu, X.; Wojtas, L.; Kim, M. M.; Zhang, X. P. J. Am. Chem. Soc. 2012, 134, 19981.
27. Xia, L.; Lee, Y. R. Eur. J. Org. Chem. 2014, 3430.
28. Zhao, X.; Zhang, Y.; Wang, J. Chem. Commun. 2012, 10162.
29. Swenson, A. K.; Higgins, K. E.; Brewer, M. G.; Brennessel, W.W.; Coleman, M. G. Org. Biomol. Chem. 2012, 10, 7483.
30. (a) Zhou, L.; Ma, J.; Zhang, Y.; Wang, J. Tetrahedron Lett. 2011, 52, 5484;
31. (b) Zhou, L.; Ma, J.; Zhang, Y.; Wang, J. Tetrahedron Lett. 2013, 54, 2558.
32. Hassink, M.; Liu, X.; Fox, J. M. Org. Lett. 2011, 13, 2388.
33. Suarez, A.; Fu, G. C. Angew. Chem., Int. Ed. 2004, 43, 3580.
34. Davies, J. R.; Kane, P. D.; Moody, C. J. Tetrahedron 2004, 60, 3967.
35. Ma, S.; Zhang, J. J. Am. Chem. Soc. 2003, 125, 12386.
36. Aoyama, T.; Nagaoka, T.; Takido, T.; Kodomari, M. Synthesis 2011, 4, 619.
37. He, C.; Guo, S.; Ke, J.;Hao, J.; Xu,H.; Chen, H.; Lei,A. J.Am. Chem. Soc. 2012,134, 5766.
38. Kretchmer, R. A.; Laitar, R. A. J. Org. Chem. 1978, 43, 4597.
39. Li, C.; Zeng, Y.; Wang, J. Tetrahedron Lett. 2009, 50, 2956