Palladium-catalyzed heteroannulation of o-alkynylphenols with propargyl carbonates. A synthesis of 2-substituted-3-allenylbenzo[b]furans

Synlett

Volumn , Issue 10, 1998, Pages 1111-1113

  Monteiro, Nuno ^a   Arnold, Andreas ^a   Balme, Geneviève ^a  

^a UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000287181     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1868     Document Type: Article

References (16)

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2. Donnelly, D.M.X. and Meegan, M. J. in Comprehensive Heterocyclic Chemistry, vol.4, pp. 657-712, A.R. Katritzky and C.W. Rees, Eds., Pergamon Press, Oxford, 1984.
3. Sundberg, R.J.; Van Nguyen, P. in "Progress in Heterocyclic Chemistry", Vol. 5, H. Suschitzky and E.F.V. Scriven, Eds., Pergamon Press, 1993, p. 129.
4. a) Arcadi, A.; Cacchi, S.; Del Rosario, M.; Fabrizi, G. Marinelli, F. J. Org. Chem., 1996, 61, 9280 and references cited therein.
5. b) Monteiro, N.; Balme G. Synlett, 1998, 746.
6. Bouyssi, D.; Goré, J.; Balme, G.; Louis, D.; Wallach, J. Tetrahedron Lett., 1993, 34, 3129.
7. Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron Lett., 1992, 33, 2811.
8. Cavicchioli, M.; Decortiat, S.; Bouyssi, D.; Goré, J.; Balme, G. Tetrahedron, 1996, 52, 11463.
9. Cavicchioli, M.; Sixdenier, E; Derey, A.; Bouyssi, D.; Balme, G. Tetrahedron Lett, 1997, 38, 1763.
10. Marat, X.; Monteiro, N.; Balme, G. Synlett, 1997, 845.
11. Bouyssi, D.; Cavicchioli, M.; Balme, G. Synlett, 1997, 944.
12. Kundu, N.G.; Pal, M.; Mahanty, J.S.; De, M. J. Chem. Soc., Perkin Trans. 1, 1997, 2815. See also ref 2a.
13. 2O); 81.7, 98.2 (C=C=C); 111.3, 120.7, 122.8, 124.8, 127.8, 128.0, 128.3, 128.5, 137.9, 149.5, 154.7 (-C=); 204.4 (C=C=C).
14. For an excellent review on σ-allenylpalladium complexes see Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons, 1995, pp 453-471.
15. a) A similar strategy leading to another class of 3-allenylbenzo-[b]furans has just been reported: Cacchi, S.; Fabrizi, G.; Moro, L. Tetrahedron Lett., 1998, 39, 5101.
16. Godfrey Jr., J.D.; Mueller, R.H.; Sedergran, T.C.; Soundararajan, N.; Colandrea, V.J. Tetrahedron Lett., 1994, 35, 6405.