Synthesis of 3-trifluoroethylfurans by palladium-catalyzed cyclization- isomerization of (Z)-2-alkynyl-3-trifluoromethyl allylic alcohols

Journal of Organic Chemistry

Volumn 65, Issue 7, 2000, Pages 2003-2006

  Qing, Feng Ling ^a   Gao, Wen Zhong ^a   Ying, Jiewen ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; FURAN DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYCLIZATION; IODINATION; ISOMERISM; SYNTHESIS;

EID: 0034616109     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991463u     Document Type: Article

References (52)

1. (a) Welch, J. T. Tetrahedron 1987, 43, 3123.
2. (b) Welch, J. T.; Eswarakrishnan, S. Fluorine in Bioorganic Chemistry; John Wiley & Sons: New York, 1991.
3. (c) Filler, R., Kobayashi, Y., Yagupolskii, L. M., Eds. Organofluorine Compounds in Medicinal and Biochemical Applications; Elsevier: Amsterdam, 1993.
4. (d) Resnati, G.; Soloshnok, V. A. Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Tetrahedron Symposia in-Print No. 58; Tetrahedron 1996, 52, 1.
5. (d) Resnati, G.; Soloshnok, V. A. Fluoroorganic Chemistry: Synthetic Challenges and Biomedical Rewards; Tetrahedron Symposia in-Print No. 58; Tetrahedron 1996, 52, 1.
6. (a) Liu, Y. S.; Purrington, S. T.; Huang, W. Y.J. Org. Chem. 1998, 63, 5623.
7. (b) McAtee, J. J.; Schinazi, R. F.; Liotta, D. C. J. Org. Chem. 1998, 63, 2161.
8. (c) Jiang, J.; DeVita, R. J.; Doss, G. A.; Goulet, M. T.; Wyvratt, M. J. J. Am. Chem. Soc. 1999, 121, 593.
9. (d) Dieter, G.; Elilitz, H.; Pulst, M.; Riedel, D.; Wecks, M. J. Fluorine Chem. 1999, 94, 91.
10. (a) Lipshutz, B. H. Chem. Rev. 1986, 96, 795.
11. (b) 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.
12. (a) Forrest, A. K.; Ohanlon, P. J. Tetrahedron Lett. 1995, 36, 2117.
13. (b) Sham, H. L.; Betebenner, D. A. J. Chem. Soc., Chem. Commun. 1991, 1134.
14. (a) Naumann, D.; Kischkowitz, J. J. Fluorine Chem. 1990, 47, 283.
15. (b) Naumann, D.; Wilkes, B.; Kischkowitz, J. J. Fluorine Chem. 1985, 30, 73.
16. (c) Sawada, H.; Nakayaa., M. J. Fluorine Chem. 1990, 46, 423.
17. (d) Cigaek, E.; Krespan, C. G. J. Org Chem. 1968, 33, 541.
18. (e) Kawada, K.; Kitagawa, O.; Kobayashi, Y. Chem. Pharm. Bull. 1985, 33, 3670.
19. (f) Smith, J. O.; Mandal. B. K.; Filler, R.; Beery, J. W. J. Fluorine Chem. 1997, 81, 123.
20. (g) Burger, K.; Helmreich, B. J. Chem. Soc., Chem. Commun. 1992, 348.
21. (h) Bambury, B. E.; Yaktin, H. K.; Wyckoff, K. K. J. Heterocycl. Chem. 1968, 5, 95.
22. (a) 2-(Dihydroperfluorooctyl)furan was prepared: Umemoto, T.; Gotou, Y. J. Fluorine Chem. 1986, 31, 231. (b) 2,2,2-Trifluoro-1-(2- furyl)ethyl phenyl sulfide, a precusor for the synthsis of 2-trifluoroethylfuran, had been prepared. Uneyama, K.; Momota, M.; Hayashida, K.; Itoh, T. J. Org. Chem. 1990, 55, 5364.
23. (a) 2-(Dihydroperfluorooctyl)furan was prepared: Umemoto, T.; Gotou, Y. J. Fluorine Chem. 1986, 31, 231. (b) 2,2,2-Trifluoro-1-(2-furyl)ethyl phenyl sulfide, a precusor for the synthsis of 2-trifluoroethylfuran, had been prepared. Uneyama, K.; Momota, M.; Hayashida, K.; Itoh, T. J. Org. Chem. 1990, 55, 5364.
24. Fuchigami, T.; Ichikawa, S. J. Org. Chem. 1994, 59, 607 and references therein.
25. Montanari, V.; Resnati, G. Tetrahedron Lett. 1994, 35, 8015 and references therein.
26. (a) Cloux, R.; Kovats, E. Synthesis 1992, 409.
27. (b) Long, Z. Y.; Chen, Q. Y. Tetrahedron Lett. 1998, 39, 8487.
28. (a) Yamazaki, T.; Mizutani, K.; Kitazume, T. J. Org. Chem. 1995, 60, 6046.
29. (b) Katritzky, A. R.; Qi, M.; Wells, A. P. J. Fluorine Chem. 1996, 80, 145.
30. Qing, F. L.; Zhang, Y. Tetrahedron Lett. 1997, 38, 6729.
31. 2H as an external standard, upfield positive.
32. (a) Hanzawa, Y.; Kawagoe, K. I.; Tanahashi, N.; Kobayashi, Y. Tetrahedron Lett. 1984, 25, 4749.
33. (b) Morikawa, T.; Uejima, M.; Kobayashi, Y.; Taguichi, T. J. Fluorine Chem. 1993, 65, 79.
34. Sonogashira, K. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: Oxford, 1991; Vol. 3, Chapter 2.4, pp 521-529.
35. Recent examples of trifluoromethyl-containing compounds in palladium-catalyzed cross-coupling reaction: (a) Uneyama, K.; Watanabe, H. Tetrahedron Lett. 1991, 32, 1459. (b) Prie, G.; Thibonnet, J.; Abarbri, M.; Duchene, A.; Parrain, J. L. Synlett 1998, 839. (c) Jiang, B.; Xu, Y. Tetrahedron Lett. 1992, 33, 511.
36. Recent examples of trifluoromethyl-containing compounds in palladium-catalyzed cross-coupling reaction: (a) Uneyama, K.; Watanabe, H. Tetrahedron Lett. 1991, 32, 1459. (b) Prie, G.; Thibonnet, J.; Abarbri, M.; Duchene, A.; Parrain, J. L. Synlett 1998, 839. (c) Jiang, B.; Xu, Y. Tetrahedron Lett. 1992, 33, 511.
37. Recent examples of trifluoromethyl-containing compounds in palladium-catalyzed cross-coupling reaction: (a) Uneyama, K.; Watanabe, H. Tetrahedron Lett. 1991, 32, 1459. (b) Prie, G.; Thibonnet, J.; Abarbri, M.; Duchene, A.; Parrain, J. L. Synlett 1998, 839. (c) Jiang, B.; Xu, Y. Tetrahedron Lett. 1992, 33, 511.
38. (a) Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1993, 58, 3435.
39. (b) Marshall, J. A.; DuBay, W. J. J. Org. Chem. 1994, 59, 1703.
40. (c) Marshall, J. A.; Bennett, C. E. J. Org. Chem. 1994, 59, 6110.
41. (a) Seiller, B.; Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1994, 493.
42. (b) Seiller, B.; Bruneau, C.; Dixneuf, P. H. Tetrahedron 1995, 51, 13089.
43. (a) Larock, R. C.; Doty, M. J.; Han, X. Tetrahedron Lett. 1998, 39, 5143.
44. (b) Gabriele, B.; Salerno, G. J. Chem. Soc., Chem. Commun. 1997, 1083.
45. (c) Wakabayashi, Y.; Fukuda, Y.; Shiragami, H.; Utimoto, K. Tetrahedron 1985, 41, 3655.
46. (d) Fukuda, Y.; Shiragami, H.; Utimoto, K.; Nozaki, H. J. Org. Chem. 1991, 56, 5816.
47. (e) Gabriele, B.; Salerno, G.; Lauria, E. J. Org. Chem. 1999, 64, 7687.
48. (a) Marshall, J. A.; Sehon, C. A. Org. Synth. 1999, 76, 263.
49. (b) Marshall, J. A.; Sehon, C. A. J. Org. Chem. 1995, 60, 5966.
50. Trost, B. M.; McIntosh, M. C. J. Am. Chem. Soc. 1995, 117, 7255.
51. Henne, H. L.; Nager, M. J. Am. Chem. Soc. 1951, 73, 1042.
52. MacInnes, I.; Walton, J. C.J. Chem. Soc, Perkin Trans 2 1987, 1077.