Palladium-Imidazolium Carbene Catalyzed Mizoroki-Heck Coupling with Aryl Diazonium Ions

Organic Letters

Volumn 4, Issue 12, 2002, Pages 2079-2082

  Andrus, Merritt B ^a   Song, Chun ^a   Zhang, Jiuqing ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIAZONIUM COMPOUND; IMIDAZOLE DERIVATIVE; ION; PALLADIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

CATALYSIS; DIAZONIUM COMPOUNDS; IMIDAZOLES; IONS; PALLADIUM;

EID: 0037071945     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025961s     Document Type: Article

References (27)

1. (a) Whitcombe, N. J.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449-7476.
2. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
3. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000. Use of tert-butylphosphine at elevated temperature: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132.
4. Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989-7000. Use of tert-butylphosphine at elevated temperature: Shaughnessy, K. H.; Kim, P.; Hartwig, J. F. J. Am. Chem. Soc. 1999, 121, 2123-2132.
5. (a) Negishi, E.; Coperet, C.; Ma, S.; Liou, S.-Y.; Liu, F. Chem. Rev. 1996, 96, 365.
6. (b) Grigg, R.; Longanathan, V.; Santhakumar, V.; Sridharan, V.; Teasdale, A. Tetrahedron Lett. 1991, 32, 687-690.
7. (a) Akiyama, F.; Miyazaki, H.; Kaneda, K.; Teranishi, S.; Fujiwara, Y. J. Org. Chem. 1980, 45, 2359-2364.
8. (b) Kikukara, K.; Nagira, K.; Wada, F.; Matsuda, T. Tetrahedron 1981, 37, 31-35.
9. (c) Sengupta, S.; Bhattacharyya, S. J. Chem. Soc., Perkin Trans. 1 1993, 1943-1947.
10. (a) Brunner, H.; Le Cousturier de Courcy, N.; Genet, J. P. Tetrahedron Lett. 1999, 40, 4815-4818.
11. (b) Severino, E. A.; Correia, C. R. D. Org. Lett. 2000, 2, 3039-3042.
12. (a) Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953.
13. (b) Lee, H. M.; Nolan, S. P. Org. Lett. 2000, 2, 2053.
14. (c) Yang, C.; Lee, H. M.; Nolan, S. P. Org. Lett. 2001, 3, 1511.
15. (d) Fürstner, A.; Leitner, A. Synlett 2001, 290-292.
16. Andrus, M. B.; Song, C. Org. Lett. 2001, 3, 3761-3764.
17. (a) Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. J. Unverzagt, M. Tetrahedron 1999, 55, 14523.
18. (b) Saba, S.; Brescia, A. M.; Kaloustian, M. K. Tetrahedron Lett. 1991, 32, 5031.
19. Herrmann, W. A.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.
20. Huang, J.; Nolan, S. P. J. Am. Chem. Soc. 1999, 121, 9889.
21. Grasa, G. A.; Nolan, S. P. Org. Lett. 2001, 3, 119.
22. McGuinness, D. S.; Cavell, K. J. Organometallics 2000, 19, 741.
23. 1H NMR (300 MHz). When sodium tert-butoxide and ligand were mixed under similar conditions, a black precipitate resulted. Further studies to establish the structure of the actual catalyst in this case will be reported elsewhere.
24. Doyle, M. P.; Siegfreid, B.; Elliot, R. C.; Dellaria, J. F. J. Org. Chem. 1977, 42, 2431.
25. 2, and N,N-bis(2,6-diisopropyl)dihydroimidazolium chloride were added, and the reaction was allowed to warm. The product was isolated and characterized as before. See the Supporting Information for details.
26. (a) Herrmann, W. A.; Goossen, L. J.; Kocher, C.; Artus, G. R. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2805.
27. (b) Herrmann, W. G.; Goossen, L. J.; Spiegler, M. Organometallics 1998, 17, 2162.