Palladium-catalyzed amination of aryl iodides

Journal of Organic Chemistry

Volumn 61, Issue 3, 1996, Pages 1133-1135

  Wolfe, John P ^a   Buchwald, Stephen L ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 5144228478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951844h     Document Type: Article

References (21)

1. (a) D'Aproano, G.; Schiavon, G.; Zotti, G.; Leclerc, M. Chem. Mater 1995, 7, 33-42.
2. (b) Loutfy, R. O.; Hsiao, C. K.; Kazmaier, P. M. Photogr. Sci. Eng. 1983, 27, 5-9.
3. (c) Negwer, M. Organic-Chemical drugs and their synonyms (an international survey); 7th. ed.; Akademie Verlag GmbH; Berlin, 1994.
4. (a) March, J. Advanced Organic Chemistry; 4th ed.; John Wiley & Sons: New York, 1992; pp 641-676.
5. (b) Mitchell, H.; Leblanc, Y. J. Org. Chem. 1994, 59, 682-687.
6. ten Hoeve, W.; Kruse, C. G.; Luteyn, J. M.; Thiecke, J. R. G.; Wynberg, H. J. Org. Chem. 1993, 58, 5101-5106.
7. Banfi, A.; Bartoletti, M.; Bellora, E.; Bignotti, M.; Turconi, M. Synthesis 1994, 777-778.
8. (e) Finet, J. P.; Khamsi, J.; Barton, D. H. R. Tetrahedron Lett. 1986, 27, 3615-3618.
9. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927-928.
10. (a) Guram, A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901-7902.
11. (b) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348-1350.
12. Hartwig has reported related results: Louie, J.; Hartwig, J.F. Tetrahedron Lett. 1995, 36, 3609-3612.
13. Typical reation times are 3-6 h for coupling secondary amines with electron-rich halides, 6-15 h for electron-poor halides, and 6-15 h for coupling reactions with primary amines.
14. Widenhoefer, R.; Zhong, H.; Buchwald, S. L. Unpublished results.
15. 3 to achieve 100% conversion.
16. Horner, L.; Meisel, K. Werkst. Korros. 1978, 29, 654-664.
17. Kanner, C. B.; Pandit, U. K. Tetrahedron 1982, 38, 3597-3604.
18. Tsuji, Y.; Huh, K. T.; Ohsugi, Y.; Watanabe, Y. J. Org. Chem. 1985, 50, 1360-1370.
19. Watanabe, Y.; Tsuje, Y.; Ige, H.; Ohsugi, Y.; Ohta, T. J. Org Chem. 1984, 49, 3359-3363.
20. Kricka, L. J.; Vernon, J. M. Can. J. Chern, 1974, 52, 299-302.
21. Amatore, C.; Jutand, A.; Negri, S.; Fauvarque, J. F. J. Organomet. Chem. 1990, 390, 389-398.