Palladium-catalyzed cyclization of o-alkynylphenols with allyl carbonates. A regioselective synthesis of 2-substituted-3-allylbenzo[b]furans

Synlett

Volumn , Issue 7, 1998, Pages 741-745

  Cacchi, Sandro ^a   Fabrizi, Giancarlo ^a   Moro, Leonardo ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002851002     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1758     Document Type: Article

References (43)

1. For a recent leading reference, see: (a) Cacchi, S.; Fabrizi, G.; Marinelli, F.; Moro, L.; Pace, P. Synlett 1997, 1363.
2. (b) Cacchi, S.; Fabrizi, G.; Moro, L. J. Org. Chem. 1997, 62, 5327.
3. (c) Bouyssi, D.; Cavicchioli, M.; Balme, G. Synlett 1997, 944.
4. (d) Arcadi, A. Synlett 1997, 941.
5. (e) Arcadi, A.; Anacardio, R.; D'Anniballe, G.; Gentile, M. Synlett 1997, 1315.
6. (f) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G.; Marinelli, F. J. Org. Chem. 1996, 61, 9280.
7. (g) Cavicchioli, M.; Decortiat, S.; Bouyssi, D.; Gore, J.; Balme, G. Tetrahedron 1996, 52, 11463.
8. (h) Arcadi, A.; Rossi, E. Tetrahedron Lett. 1996, 37, 6811.
9. (i) Saulnier, M.G.; Frennessen, D.B.; Deshpande, M.S.; Vyas, D.M. Tetrahedron Lett. 1995, 36, 7841.
10. (j) Arcadi, A.; Cacchi, S.; Carnicelli, V.; Marinelli, F. Tetrahedron 1994, 50, 437.
11. (k) Balme, G.; Bouyssi, D. Tetrahedron 1994, 50, 403.
12. (l) Arcadi, A.; Cacchi, S.; Larock, R.C.; Marinelli, F. Tetrahedron Lett. 1993, 34, 2813.
13. (m) Bouyssi, D.; Gore, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett. 1993, 34, 3129.
14. Mandai, T.; Ohta, K.; Baba, N.; Kawada, M.; Tsuji, J. Synlett 1992, 671.
15. Tsuda, T.; Ohashi, Y.; Nagahama, N.; Sumiya, R.; Saegusa, T. J. Org. Chem. 1988, 53, 2650.
16. Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 62, 1001.
17. 2: C, 80.33; H, 5.40. Found: C, 80.39; H, 5.45.
18. Goux, C.; Lhoste, P.; Sinou, D. Synlett 1992, 725.
19. 20O: C, 86.91; H, 7.30. Found: C, 86.87; H, 7.31.
20. +, 96), 233 (80), 194 (100).
21. 14O: C, 87.14; H, 6.03. Found: C, 87.20; H, 6.09.
22. Kurosawa, H.; Shiba, K.; Hirako, K.; Kakiuchi, K.; Ikeda, I. J. Chem. Soc., Chem. Commun. 1994, 1099.
23. Trost, B.M.; Weber, L.; Strege, P.E.; Fullerton, T.J.; Dietsche, T.J. J. Am. Chem. Soc. 1978, 100, 3416.
24. Keinan, E.; Sahai, M. J. Chem. Soc., Chem. Commun. 1984, 648.
25. Temple, J.S.; Riediker, M.; Schwartz, J. J. Am. Chem. Soc. 1982, 104, 1310.
26. Hayasi, Y.; Riediker, M.; Temple, J.S.; Schwartz, J. Tetrahedron Lett. 1981, 22, 2629.
27. Aranyos, A.; Szabo, K.J., Castaño, A.M.; Bäckvall, J.-E. Organometallics 1997, 16, 1058.
28. Togni, A.; Burckhardt, U.; Gramlich, V.; Pregosin, P.S.; Salzmann, R. J. Am. Chem. Soc. 1996, 118, 1031.
29. Szabó, K.J. Organometallics 1996, 15, 1128.
30. Szabó, K.J. J. Am. Chem. Soc. 1996, 118, 7818.
31. Ward, T.R. Organometallics 1996, 15, 2836.
32. Castaño, A.M.; Aranyos, A.; Szabó, K.J.; Bäckvall, J.-E. Angew. Chem. Int. Ed. Engl. 1995, 34, 2551.
33. Hoffmann, H.M.R.; Otte, A.R.; Wilde, A.; Menzer, S.; Wiliams, D.J. Angew. Chem. Int. Ed. Engl. 1995, 34, 100.
34. Åkermark, B.; Krakenberger, B.; Hansson, S.; Krakenberg, B.; Vitagliano, A. J. Organomet. Chem. 1987, 335, 133.
35. Åkermark, B.; Krakenberger, B.; Hansson, S.; Vitagliano, A. Organometallics 1987, 6, 620.
36. Åkermark, B.; Vitagliano, A. Organometallics 1985, 4, 1275.
37. Åkermark, B.; Hansson, S.; Krakenberger, B.; Vitagliano, A.; Zettreberg, K. Organometallics 1984, 3, 679.
38. Appleton, T.G.; Clark, H.C.; Manzer, L.E. Coord. Chem. Rev. 1973, 10, 335.
39. Faller, J.W.; Mattina, M.J. Inorg. Chem. 1972, 11, 1296.
40. Faller, J.W; Incoura, M.J. J. Organomet. Chem. 1969, 19, P13.
41. Wada, M.; Higashizaki, S. J. Chem. Soc., Chem. Commun. 1984, 482.
42. Tolman, C.A. Chem. Rev. 1977, 77, 313.
43. A similar approach to the synthesis of 2-substituted-3-allyl-benzo[b]furans has been developed independently by Balme and coworkers: Synlett 1998, 746.