Palladium-catalyzed suzuki coupling with terminal alkynes - Application to the synthesis of 2,3-disubstituted benzo[b]furans

European Journal of Organic Chemistry

Volumn , Issue 15, 2005, Pages 3334-3341

  Colobert, Françoise ^a   Castanet, Anne Sophie ^a   Abillard, Olivier ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Alkynes; Benzofuran; Iodocyclisation; Palladium; Suzuki reaction

Indexed keywords

EID: 23044454240     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500166     Document Type: Article

References (38)

1. a) A. R. Katritzky, in Advances in Heterocyclic Chemistry, Academic Press, New York, 1982;
2. b) G. Vernin, in The Chemistry of Heterocyclic Flavouring and Aroma Compounds, Hellis Horwood, Chichester, 1982;
3. c) A. R. Katritzky, C. W. Rees, in Comprehensive Heterocyclic Chemistry, Pergamon, New York, 1984;
4. d) H. B. Lipshutz, Chem. Rev. 1986, 86, 795-819;
5. e) C. C. Felder, K. E. Joyce, E. M. Briley, M. Glass, K. P. Mackie, K. J. Fahey, G. J. Cullinan, D. C. Hunden, D. W. Johnson, M. O. Chaney, G. A. Koppel, M. Brownstein, J. Pharmacol. Exp. Ther. 1998, 291-297.
6. A. Gangjee, R. Devraj, J. J. Mc Guire, R. L. Kisliuk, J. Med. Chem. 1995, 38, 3798-3805.
7. Z. Yang, H. B. Liu, C. M. Lee, H. M. Chang, H. N. Wong, J. Org. Chem. 1992, 57, 7248-7257.
8. K. A. Ohemeng, M. A. Appolina, V. N. Nguyen, C. F. Schwender, M. Singer, M. Steber, J. Ansell, D. Argentieri, W. Hageman, J. Med. Chem. 1994, 37, 3663-3667.
9. T. Nagahara, Y. Yokoyama, K. Inamura, S. Katakura, S. Komoriya, H. Yamaguchi, T. Hara, M. Iwamoto, J. Med. Chem. 1994, 37, 1200-1207.
10. A. P. Kozikowsky, D. Ma, L. Du, N. E. Lewin, P. M. Blumberg, J. Am. Chem. Soc. 1995, 117, 6666-6672.
11. G. A. Carter, K. Chamberlain, R. L. Wain, Ann. Appl. Biol. 1978, 88, 57-64.
12. a) A. Fürstner, D. N. Jumbam, Tetrahedron 1992, 48, 5991-6010;
13. b) R. S. Givens, P. S. Athey, B. Matuszewski, L. W. Kuepper, J. Xue, T. Fister, J. Am. Chem. Soc. 1993, 115, 6001-6012;
14. c) D. Hellwinkel, K. Göke, Synthesis 1995, 1135-1141;
15. d) X. Du, R. W. Armstrong, J. Org. Chem. 1997, 62, 5678-5679;
16. e) Y. Ito, T. Aoyama, T. Shioiri, Synlett 1997, 1163-1164;
17. f) C. Fuganti, S. Serra, Tetrahedron Lett. 1998, 39, 5609-5610;
18. g) D. D. Hennings, S. Iwasa, V. H. Rawal, Tetrahedron Lett. 1997, 38, 6379-6382.
19. a) N. J. Kundo, M. Pal, J. S. Mahanty, M. J. De, J. Chem. Soc. Perkin Trans. 1 1997, 2815-2820;
20. b) Y. Kondo, F. Shiga, N. Murata, T. Sakamoto, H. Yamanaka, Tetrahedron 1994, 50, 11803-11812;
21. c) A. Arcadi, S. Cacchi, M. Del Rosario, G. Fabrizi, F. Marinelli, J. Org. Chem. 1996, 61, 9280-9288;
22. d) N. Monteiro, G. Balme, Synlett 1998, 746-747;
23. e) N. Monteiro, A. Arnold, G. Balme, Synlett 1998, 1111-1113.
24. a) S. Cacchi, J. Organomet. Chem. 1999, 576, 42-64;
25. b) A. Arcadi, S. Cacchi, F. Marinelli, Synthesis 1986, 749-751;
26. c) A. Arcadi, S. Cacchi, G. Fabrizi, F. Marinelli, L. Moro, Synlett 1999, 9, 1432-1434;
27. d) R. C. Larock, E. K. Yum, M. J. Doty, K. K. C. Sham, J. Org. Chem. 1995, 60, 3270-3271;
28. e) C. Amatore, E. Blart, J. P. Genêt, A. Jutand, S. Lemaire-Audoire, M. Savignac, J. Org. Chem. 1995, 60, 6829-6839.
29. A.-S. Castanet, F. Colobert, T. Schlama, Org. Lett. 2000, 2, 3559-3561.
30. Contrary, using o-(tert-butyldimethylsilyloxy)bromobenzene the reaction was unreproducible, affording 2-bromophenol, starting material, coupling product and 2-hexylbenzo[b]furan in varying ratios.
31. For other examples of iodine-promoted electrophilic cyclization of alkynes to give heterocycles, see: a) A. Arcadi, S. Cacchi, S. Di Giuseppe, G. Fabrizi, F. Marinelli, Org. Lett. 2002, 4, 2409-2412;
32. b) T. Yao, M. A. Campo, R. C. Larock, Org. Lett. 2004, 6, 2677-2680.
33. Y. Ma, C. Song, W. Jiang, Q. Wu, Y. Wang, X. Liu, M. B. Andrus, Org. Lett. 2003, 5, 3317-3319.
34. G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017-8028.
35. D. Gelman, S. L. Buchwald, Angew. Chem. Int. Ed. 2003, 42, 5993-5996.
36. H. Sashida, A. Kuroda, J. Chem. Soc. Perkin Trans. 1 2000, 1965-1969.
37. D. R. Buckle, C. J. M. Rockell, J. Chem. Soc. Perkin Trans. 1 1985, 2443-2446.
38. Y. Hu, K. J. Nawoschik, Y. Liao, J. Ma, R. Fathi, Z. Yang, J. Org. Chem. 2004, 69, 2235-2239.