Palladium-catalyzed coupling of ammonia and lithium amide with aryl halides

Journal of the American Chemical Society

Volumn 128, Issue 31, 2006, Pages 10028-10029

  Shen, Qilong ^a   Hartwig, John F ^a  

^a YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIA; HALIDE; LITHIUM AMIDE; LITHIUM DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; CATALYSIS; CONCENTRATION (PARAMETERS); METAL BINDING; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION;

AMIDES; AMMONIA; CATALYSIS; HALOGENS; LITHIUM; PALLADIUM;

EID: 33746931578     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064005t     Document Type: Article

References (35)

1. (a) LeBlanc, J. R. J.; Madhavan, S.; Porter, R. E.; Kellogg, P. Encyclopedia of Chemical Technology, 2nd ed.; Wiley: New York, 1963; Vol. 2.
2. (a) Gross, T.; Seayad, A. M.; Ahmad, M.; Beller, M. Org. Lett. 2002, 4, 2055.
3. (b) Roundhill, D. M. Chem. Rev. 1992, 92, 1.
4. (c) Zimmermann, B.; Herwig, J.; Beller, M. Angew. Chem., Int. Ed. 1999, 38, 2372.
5. (d) Prinz, T.; Driessen-Holscher, B. Chem.-Eur. J. 1999, 5, 2069.
6. (e) Prinz, T.; Keim, W.; Driessen-Holscher, B. Angew. Chem., Int. Ed. Engl. 1996, 35, 1708.
7. (f) Ogo, S.; Uehara, K.; Abura, T.; Fukuzumi, S. J. Am. Chem. Soc. 2004, 126, 3020.
8. (a) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E. I., Ed.; Wiley-Interscience: New York, 2002; Vol. 1, p 1051.
9. (b) Hartwig, J. F. In Modern Arene Chemistry; Astruc, C., Ed.; Wiley-VCH: Weinheim, Germany, 2002, p 107.
10. (c) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
11. (a) Weissermel, K.; Arpe, H. J. Industrial Organic Chemistry; Wiley-VCH: Weinheim, Germany, 1997.
12. (b) Lawrence, S. A. Amines: Synthesis, Properties, and Application; Cambridge University Press: Cambridge, 2004.
13. Lang, F.; Zewge, D.; Houpis, I. N.; Volante, R. P. Tetrahedron Lett. 2001, 42, 3251.
14. (a) Jaime-Figueroa, S.; Liu, Y.; Muchowski, J. M.; Putman, D. G. Tetrahedron Lett. 1998, 39, 1313.
15. (b) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
16. (c) Wolfe, J. P.; Åhman, J.; Sadighi, J. P.; Singer, R. A.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6367.
17. (d) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J. J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
18. (e) Grasa, G. A.; Viciu, M. S.; Huang, J. K.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
19. (f) Barluenga, J.; Aznar, F.; Valdes, C. Angew. Chem., Int. Ed. 2004, 43, 343.
20. Huang, X. H.; Buchwald, S. L. Org. Lett. 2001, 3, 3417.
21. Huang, X. H.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
22. (a) Lee, S.; Jorgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729.
23. (b) Lee, D.-Y.; Hartwig, J. F. Org. Lett. 2005, 7, 1169.
24. (a) Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 2755.
25. (b) Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 3534.
26. (c) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
27. (a) Park, S.; Rheingold, A. L.; Roundhill, D. M. Organometallics 1991, 10, 615.
28. (b) Casalnuovo, A. L.; Calabrese, J. C.; Milstein, D. Inorg. Chem. 1987, 26, 971.
29. (a) Togni, A.; Breutel, C.; Schnyder, A.; Spindler, F.; Landert, H.; Tijani, A. J. Am. Chem. Soc. 1994, 116, 4062.
30. (b) Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371.
31. (c) Fernández-Rodríguez, M. A.; Shen, Q.; Hartwig, J. F. J. Am. Chem. Soc. 2006, 128, 2180.
32. Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746.
33. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718.
34. Stauffer, S.; Hauck, S. I.; Lee, S.; Stambuli, J.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
35. Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.