Synthesis of multisubstituted furans via copper-catalyzed intramolecular O-vinylation of ketones with vinyl bromides

Tetrahedron Letters

Volumn 51, Issue 28, 2010, Pages 3678-3681

  Chen, Liqun ^a   Fang, Yewen ^b   Zhao, Qiwu ^b   Shi, Min ^a,b   Li, Chaozhong ^b  

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

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3,4,7,8 TETRAMETHYL 1,10 PHENANTHROLINE; COPPER; FURAN DERIVATIVE; KETONE DERIVATIVE; OXYGEN; PHENANTHROLINE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 77954348345     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.05.040     Document Type: Article

References (48)

1. Kobayashi, J.; Watanabe, D.; Kawasaki, N.; Tsuda, M. J. Org. Chem. 1997, 62, 9236.
2. Jadulco, R.; Proksch, P.; Wray, V.; Berg, S. A.; Grafe, U. J. Nat. Prod. 2001, 64, 527.
3. Heaney, H.; Ahn, J. S.. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996; Vol.2, p 297.
4. (a) Hou, X. L.; Cheung, H. Y.; Hon, T. Y.; Kwan, P. L.; Lo, T. H.; Tong, S. Y.; Wong, H. N. C. Tetrahedron 1998, 54, 1955
5. (b) Brown, R. C. D. Angew. Chem., Int. Ed. 2005, 44, 8505
6. For selected examples, see: (a) Alcaide, B.; Almendros, P.; Campo, T. M. Eur. J. Org. Chem. 2007, 2844
7. (b) Dudnik, A. S.; Gevorgyan, V. Angew. Chem., Int. Ed. 2007, 46, 5195
8. (c) Zhou, C.-Y.; Chan, P. W. H.; Che, C. M. Org. Lett. 2006, 8, 325
9. (d) Sromek, A. W.; Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2005, 127, 10500.
10. For selected examples, see: (a) Sniady, A.; Durham, A.; Morreale, M. S.; Wheeler, K. A.; Dembinski, R. Org. Lett. 2007, 9, 1175
11. (b) Cadierno, V.; Gimeno, J.; Nebra, N. Adv. Synth. Catal. 2007, 349, 382
12. (c) Zhan, Z.-p.; Wang, S.-p.; Cai, X.-b.; Liu, H.-j.; Yu, J.-l.; Cui, Y.-Y. Adv. Synth. Catal. 2007, 349, 2097
13. (d) Dudnik, A. S.; Sromek, A. W.; Rubina, M.; Kim, J. T.; Kelin, A. V.; Gevorgyan, V. J. Am. Chem. Soc. 2008, 130, 1440.
14. Hashmi, A. S. K.; Sinha, P. Adv. Synth. Catal. 2004, 346, 432.
15. For selected examples, see: (a) Liu, Y.; Song, F.; Song, Z.; Liu, M.; Yan, B. Org. Lett. 2005, 7, 5409
16. (b) Diaz-Alvarez, A. E.; Crochet, P.; Zablocka, M.; Duhayon, C.; Cadierno, V.; Gimeno, J.; Majoral, J. P. Adv. Synth. Catal. 2006, 348, 1671
17. (c) Du, X.; Song, F.; Lu, Y.; Chen, H.; Liu, Y. Tetrahedron 2009, 65, 1839
18. For reviews, see: (a) Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428
19. (b) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
20. (c) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337
21. (d) Deng, W.; Liu, L.; Guo, Q.-X. Chin. J. Org. Chem. 2004, 24, 150
22. (e) Dehli, J. R.; Legros, J.; Bolm, C. Chem. Commun. 2005, 973
23. (f) Chemler, S. R.; Fuller, P. H. Chem. Soc. Rev. 2007, 36, 1153
24. (g) Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
25. (h) Ma, D.; Cai, Q. Acc. Chem. Res. 2008, 41, 1450
26. (i) Evano, G.; Toumi, M.; Coste, A. Chem. Commun. 2009, 4166.
27. (a) Nordmann, G.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 4978
28. (b) Wan, Z.; Jones, C. D.; Koenig, T. M.; Pu, Y. J.; Mitchell, D. Tetrahedron Lett. 2003, 44, 8257
29. (c) Ma, D.; Cai, Q.; Xie, X. Synlett 2005, 1767
30. (d) Ouali, A.; Laurent, R.; Caminade, A.-M.; Majoral, J.-P.; Taillefer, M. J. Am. Chem. Soc. 2006, 128, 15990;
31. (e) Taillefer, M.; Ouali, A.; Renard, B.; Spindler, J.-F. Chem. Eur. J. 2006, 12, 5301.
32. Miyamoto, H.; Okawa, Y.; Nakazaki, A.; Kobayashi, S. Angew. Chem., Int. Ed. 2006, 45, 2274.
33. (a) Fang, Y.; Li, C. Chem. Commun. 2005, 3574
34. (b) Fang, Y.; Li, C. J. Am. Chem. Soc. 2007, 129, 8092
35. (c) Sun, C.; Fang, Y.; Li, S.; Zhang, Y.; Zhao, Q.; Zhu, S.; Li, C. Org. Lett. 2009, 11, 4084.
36. Fang, Y.; Li, C. J. Org. Chem. 2006, 71, 6427.
37. (a) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035
38. (b) Lu, H.; Li, C. Org. Lett. 2006, 8, 5365
39. (c) Pan, Y.; Lu, H.; Fang, Y.; Fang, X.; Chen, L.; Qian, J.; Wang, J.; Li, C. Synthesis 2007, 1242
40. (d) Zhao, Q.; Li, C. Org. Lett. 2008, 10, 4037
41. (e) Lu, H.; Yuan, X.; Zhu, S.; Sun, C.; Li, C. J. Org. Chem. 2008, 73, 8665
42. (f) Chen, L.; Shi, M.; Li, C. Org. Lett. 2008, 10, 5285
43. (g) Zhao, Q.; Li, L.; Fang, Y.; Sun, D.; Li, C. J. Org. Chem. 2009, 74, 459.
44. Klapars, A.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 7421.
45. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8762.
46. Ma, D.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453.
47. Wolter, M.; Klapars, A.; Buchwald, S. L. Org. Lett. 2001, 3, 3803.
48. 3 (M): 258.1256. Found: 258.1255.