2-Substituted-3-allenyl-benzo[b]furans through the palladium-catalysed cyclization of propargylic o-(Alkynyl)phenyl ethers

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5101-5104

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

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; ALLENE DERIVATIVE; BENZOFURAN DERIVATIVE; DIPHENYL ETHER DERIVATIVE; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL REACTION; CYCLIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032499992     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00936-8     Document Type: Article

References (18)

1. 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.; Frennesson, 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. 2. Cacchi, S.; Fabrizi, G.; Pace, P. J. Org. Chem. 1998, 62, 1001.
15. 3. Cacchi, S.; Fabrizi, G.; Moro, L. Synlett submitted.
16. 3 and ttmpp in DME at 60 °C for 6 h produced 2a and 3a in 6 and 2% yield, respectively, along with other unidentified products.
17. 18O: C, 89.40; H, 5.36. Found: C, 89.43; H, 5.39.
18. 6. For other cyclizations promoted by σ-allenylpalladium complexes, see: Bouyssi, D.; Gore, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett. 1993, 34, 3129.