P(i-BuNCH2CH2)3N: An effective ligand in the palladium-catalyzed amination of aryl bromides and iodides

Journal of Organic Chemistry

Volumn 68, Issue 2, 2003, Pages 452-459

  Urgaonkar, Sameer ^a   Nagarajan, M ^a   Verkade, J G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM-CATALYZED AMINATION;

ALKALINITY; AMINATION; BROMINE COMPOUNDS; IODINE COMPOUNDS; PALLADIUM;

ORGANIC COMPOUNDS;

BROMIDE; IODIDE; LIGAND; PALLADIUM; PHOSPHINE DERIVATIVE;

AMINATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037462390     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0205309     Document Type: Article

References (45)

1. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic synthesis; John Wiley & Sons: Chichester, England, 1995. For a general review of palladium-catalyzed aryl aminations, see: (b) Wolfe, J. P. Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 805. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
2. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic synthesis; John Wiley & Sons: Chichester, England, 1995. For a general review of palladium-catalyzed aryl aminations, see: (b) Wolfe, J. P. Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 805. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
3. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic synthesis; John Wiley & Sons: Chichester, England, 1995. For a general review of palladium-catalyzed aryl aminations, see: (b) Wolfe, J. P. Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 805. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
4. (a) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic synthesis; John Wiley & Sons: Chichester, England, 1995. For a general review of palladium-catalyzed aryl aminations, see: (b) Wolfe, J. P. Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 805. (d) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
5. (a) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
6. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369. Also see ref 9.
7. (a) Guram, A. S.; Rennels, R. A.; Buchwald, S. L. Angew. Chem., Int. Ed. Engl. 1995, 34, 1348.
8. (b) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
9. (c) Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
10. (d) Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
11. (e) Wolfe, J. P.; Singer, R. A.; Yang, B. H.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 9550.
12. (a) Huang, J.; Grasa, G. A.; Nolan, S. P. Org. Lett. 1999, 1, 1307.
13. (b) Herrmann, W. A.; Kocher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163.
14. (c) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
15. (d) Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S. Organometallics 1999, 18, 1840.
16. (e) Artamkina, G. A.; Ivushkin, V. A.; Beletskaya, P. Russ. J. Org. Chem. 1970, 35, 1797.
17. (f) Bolm, C.; Hildebrand, J. P. J. Org. Chem. 2000, 65, 169.
18. (g) Li, R.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
19. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
20. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
21. (b) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K, H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
22. (a) Marcoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
23. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
24. Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158. See also ref 4d and references therein.
25. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
26. Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
27. (a) Clarke, M. L.; Cole-Hamilton, D. J.; Slawin, A. M. Z.; Woollins, J. D. Chem. Commun. 2000, 2065.
28. (b) Clarke, M. L.; Cole-Hamilton, D. J.; Woollins, J. D. J. Chem. Soc., Dalton Trans. 2001, 2721.
29. (a) Molloy, K. G.; Petersen, J. L. J. Am. Chem. Soc. 1995, 117, 7696.
30. (b) Xi, S. K.; Schmidt, H.; Lensink, C.; Kim, S.; Wintergrass, D.; Daniels, L. M.; Jacobson, R. A.; Verkade, J. G. Inorg. Chem. 1990, 29, 2214.
31. (c) Socol, S. M.; Jacobson, R. A.; Verkade, J. G. Inorg. Chem. 1984, 23, 88.
32. (d) Romming, C.; Songstad, J. Acta Chem. Scand., Ser. A 1980, 34, 365.
33. (e) Romming, C.; Songstad, J. Acta Chem. Scand., Ser. A 1979, 33, 187.
34. For a discussion of the electronic structure of tris(dialkylamino)-phosphines, see: Cowley, A. H.; Lattman, M.; Stricklen, P. M.; Verkade, J. G. Inorg. Chem. 1982, 21, 543.
35. 3 nitrogen is rather planar, the sum of angles being 354.9, 356.6, and 357.5° (Wroblewski, A. E.; Pinkas, J.; Verkade, J. G. Main Group Chem. 1995, 1, 69).
36. (a) Kisanga, P.; Verkade, J. G. Tetrahedron 2001, 57, 467 and references therein.
37. (b) Liu, X.; Verkade, J. G. Manuscript in preparation.
38. Kisanga, P. B.; Verkade, J, G.; Schwesinger, R. J. Org. Chem. 2000, 65, 5431.
39. Verkade, J. G. In New Aspects of Phosphorus Chemistry II. Top. Curr. Chem. Majoral, J. P., Ed. 2002, 233, 1.
40. Hartwig, J. F.; Richards, S.; Baranano, D.; Paul, F. J. Am. Chem. Soc. 1996, 118, 3626.
41. 3, and NaOH failed to promote coupling.
42. Widenhoefer, R. A.; Buchwald, S. L. Organometallics 1996, 15, 3534.
43. Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron Lett. 1998, 39, 5327.
44. The reaction of 1-chloro-4-iodobenzene with morpholine using the Pd/4a catalyst system (0.5 mol % Pd) gave an 85% yield of the desired product. The general protocol for the amination of aryl iodides using Pd/4a at such a low catalyst loading has not yet been fully scoped.
45. 3: $148.00 (5 g, Aldrich). 2-(Di-tert-butylphosphino)-biphenyl or 2-(dicyclohexylphosphino)biphenyl: $99.00 (2 g, Strem).