Palladium-Catalyzed Heteroannulation of 1,3-Dienes by Functionally Substituted Aryl Halides

Journal of Organic Chemistry

Volumn 55, Issue 11, 1990, Pages 3447-3450

  Larock, Richard C ^a   Berrios Pena, Norman ^a   Narayanan, Kris ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000291336     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00298a011     Document Type: Article

References (39)

1. For some other recent palladium-promoted processes for heteroannulation, see: (a) van der Louw, J.; Out, G. J. J.; van der Baan, J. L.; de Kanter, F. J. J.; Bickelhaupt, F.; Klumpp, G. W. Tetrahedron Lett. 1989, 30, 4863.
2. Ohno, K.; Mitsuyasu, T.; Tsuji, J. Tetrahedron 1972, 28, 3705.
3. Braunstein, P.; Matt, D.; Nobel, D. J. Am. Chem. Soc. 1988, 110, 3207.
4. Trost, B. M.; Bonk, P. J. J. Am. Chem. Soc. 1985, 107, 8277.
5. Trost, B. M.; King, S. A.; Schmidt, T. J. Am. Chem. Soc. 1989, 111, 5902.
6. Trost, B. M.; Bonk, P. J. J. Am. Chem. Soc. 1985, 107, 1778.
7. Trost, B. M.; King, S. A.; Nanninga, T. N. Chem. Lett. 1987, 15.
8. Trost, B. M.; King, S. A. Tetrahedron Lett. 1986, 27, 5971.;
9. Ohno, K. Tsuji, J. J. Chem. Soc., Chem. Commun. 1971, 247.
10. Larock, R. C.; Leuck, D. J.; Harrison, L. W. Tetrahedron Lett. 1988, 29, 6399.
11. Horino, H.; Inoue, N. J. Chem. Soc., Chem. Commun. 1976, 500.;
12. Horino, H. Inoue, N. Heterocycles 1978, 11, 281.
13. Larock, R. C.; Harrison, L. W.; Hsu, M. H. J. Org. Chem. 1984, 49, 3662.
14. Larock, R. C.; Song, H. Synth. Commun. 1989, 19, 1463.
15. Larock, R. C.; Varaprath, S.; Lau, H. H.; Fellows, C. A. J. Am. Chem. Soc. 1984, 106, 5274.
16. Larock, R. C.; Liu, C.L.; Lau, H. H.; Varaprath, S. Tetrahedron Lett. 1984, 25, 4459.
17. O’Connor, J. M.; Stallman, B. J.; Clark, W. G.; Shu, A. Y. L.; Spada, R. E.; Stevenson, T. M.; Dieck, H. A. J. Org. Chem. 1983, 48, 807.
18. For early work with this type of catalyst system, see: (a) Jeffery, T. J. Chem. Soc., Chem. Commun. 1984, 1287.
19. Jeffery, T. Tetrahedron Lett. 1985, 26, 2667.
20. Jeffery, T. Synthesis 1987, 70.
21. Larock, R. C.; Babu, S. Tetrahedron Lett. 1987, 28, 5291.
22. Larock, R. C.; Baker, B. E. Tetrahedron Lett. 1988, 29, 905.
23. Larock, R. C.; Song, H.; Baker, B. E.; Gong, W. H. Tetrahedron Lett. 1988, 29, 2919.
24. Larock, R. C.; Stinn, D. E. Tetrahedron Lett. 1988, 29, 4687.
25. Larock, R. C.; Gong, W. H. J. Org. Chem. 1989, 54, 2047.
26. Larock, R. C.; Gong, W. H.; Baker, B. E. Tetrahedron Lett. 1989, 30, 2603.
27. Cagniant, P.; Cagniant, D. Advances in Heterocyclic Chemistry, Academic Press: New York, 1975; Vol. 18, p 337.
28. Mustafa, A. Benzofurans; Wiley: New York, 1974; Chapter 4.
29. DeGraw, J. I., Jr.; Bowen, D. M.; Bonner, W. A. Tetrahedron 1963, 19, 19.
30. Kawase, Y.; Yamaguchi, S.; Kondo, S.; Shimokawa, K. Chem. Lett. 1978, 253.
31. Yamaguchi, S.; Kondo, S.; Shimokawa, K.; Inoue, O.; Sannomiya, M.; Kawase, Y. Bull. Chem. Soc. Jpn. 1982, 55, 2500.
32. Bigi, F.; Casiraghi, G.; Casnati, G.; Sartori, G. Tetrahedron 1983, 39,169.
33. Kawase, Y.; Yamaguchi, S.; Inoue, O.; Sannomiya, M.; Kawabe, K. Chem. Lett. 1980, 1581.
34. Duffley, R. P.; Stevenson, R. J. Chem. Res. 1978, (S) 468; (M) 5451.
35. Donnelly, D. M. X.; O’Reilly, J. O. J. Chem. Res. 1980, (S) 1; (M) 0127.
36. Takahashi, K.; Miyake, A.; Hata, G. Bull. Chem. Soc. Jpn. 1972, 45, 230.
37. Stanton, S. A.; Felman, S. W.; Parkhurst, C. S.; Go-dleski, S. A. J. Am. Chem. Soc. 1983, 105, 1964.
38. Stork, G.; Poirier, J. M. J. Am. Chem. Soc. 1983, 105, 1073.
39. Keinan, E.; Seth, K. K.; Lamed, R. J. Am. Chem. Soc. 1986, 108, 3474.