Scope and limitations of Pd2(dba)3/P(i-BuNCH 2CH2)3N-catalyzed Buchwald-Hartwig amination reactions of aryl chlorides

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9135-9142

  Urgaonkar, Sameer ^a   Verkade, John G ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINATION; CATALYSTS; FUNCTIONAL POLYMERS; PALLADIUM COMPOUNDS; SODIUM COMPOUNDS; SUBSTRATES;

ACTIVE CATALYSTS; ARYL CHLORIDES; FUNCTIONALIZED SUBSTRATES; LIGANDS;

ORGANIC COMPOUNDS;

AMINE; CHLORIDE; HETEROCYCLIC COMPOUND; LIGAND; NITROGEN DERIVATIVE; PALLADIUM COMPLEX; PHOSPHATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDINE DERIVATIVE; SODIUM HYDROXIDE;

AMINATION; ARTICLE; BUCHWALD HARTWIG AMINATION; CATALYSIS; CATALYST; REACTION ANALYSIS; STEREOSPECIFICITY;

EID: 10844220738     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048716q     Document Type: Article

References (55)

1. Kosugi, M.; Kameyama, M.; Migita, T. Chem. Lett. 1983, 927.
2. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
3. (b) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
4. (c) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
5. (a) Hartwig, J. F. In Modern Amination Methods; Ricci, A., Ed.; Wiley-VCH: Weinheim, Germany, 2000.
6. (b) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
7. (c) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
8. (a) Beland, F. A.; Kadlubar, F. F. Handbook of Experimental Pharmacology, Carcinogenesis and Mutagenesis; Grove, Springer, Verlag: Heidelberg, Germany, 1990.
9. (b) Peat, A. J.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028.
10. (c) Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112.
11. Louie, J.; Hartwig, J. F.; Fry, A. J. J. Am. Chem. Soc. 1997, 119, 11695.
12. Westmoreland, I.; Munslow, I. J.; O'Shaughnessy, P. N.; Scott, P. Organometallics 2003, 22, 2972.
13. Greco, G. E.; Popa, A. I.; Schrock, R. R. Organometallics 1998, 17, 5591.
14. Furstner, A.; Mathes, C.; Lehmann, C. W. Chem. Eur. J. 2001, 7, 5229.
15. Huyskens, F. L.; Huyskens, P. L.; Persoons, A. P. J. Chem. Phys. 1998, 108, 8161.
16. Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
17. Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575.
18. Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807.
19. Ehrentraut, A.; Zapf, A.; Beller, M. J. Mol. Catal. A: Chemical 2002, 182-183, 515.
20. Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
21. Wolfe, J. P.; Tomori, J.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
22. Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
23. Bei, X.; Uno, T.; Norris, J.; Turner, H. W.; Weinberg, W. H.; Guram, A. S.; Petersen, J. L. Organometallics 1999, 18, 1840.
24. Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229.
25. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
26. Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
27. Schnyder, A.; Indolese, A. F.; Studer, M.; Blaser, H.-U. Angew. Chem., Int. Ed. 2002, 41, 3668.
28. Zim, D.; Buchwald, S. L. Org. Lett. 2003, 5, 2413.
29. Bedford, R. B.; Blake, M. E. Adv. Synth. Catal. 2003, 345, 1107.
30. Li, G. Y.; Zheng, G.; Noonan, A. F. J. Org. Chem. 2001, 66, 8677.
31. Ligands 1, 2, and 3 are commercially available from Aldrich and Strem Chemicals, (a) For recent reviews, see: Verkade, J. G. Top. Curr. Chem. 2002, 233, 1.
32. (b) Kisanga, P. B.; Verkade, J. G. Tetrahedron 2003, 59, 7819.
33. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Tetrahedron Lett. 2002, 43, 8921.
34. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. J. Org. Chem. 2003, 68, 452.
35. Urgaonkar, S.; Nagarajan, M.; Verkade, J. G. Org. Lett. 2003, 5, 815.
36. Urgaonkar, S.; Verkade, J. G. Adv. Synth. Catal. 2004, 346, 611.
37. You, J.; Verkade, J. G. Angew. Chem., Int. Ed. 2003, 42, 5051.
38. You, J.; Verkade, J. G. J. Org. Chem. 2003, 68, 8003.
39. (a) Su, W.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2004, 6, 1421.
40. (b) Su, W.; Urgaonkar, S.; Mclaughlin, P. A.; Verkade, J. G. J. Am. Chem. Soc., in press.
41. Urgaonkar, S.; Xu, J.-H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416.
42. Our preliminary studies of Pd/3-catalyzed animations of aryl chlorides were recently communicated, see ref 28.
43. Stambuli, J. P.; Buhl, M.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 9346.
44. Vigalok, A.; Milstein, D. Acc. Chem. Res. 2001, 34, 798.
45. Broekkamp, C. L. E.; Leysen, D. B.; Peeters, W. M. M.; Pinder, R. M. J. Med. Chem. 1995, 38, 4615.
46. Hepperle, M.; Eckart, J.; Gala, D. Tetrahedron Lett. 1999, 40, 5655.
47. Hagibara, M.; Kashiwase, H.; Katsube, T.; Kimura, T.; Komai, T.; Momota, K.; Ohmine, T.; Nishigaki, T.; Kimura, S.; Shimada, K. Bioorg. Med. Chem. Lett. 1999, 9, 3063.
48. Chen, Y.-L.; Fang, K.-C.; Sheu, J.-Y.; Hsu, S.-L.; Tzeng, C.-C. J. Med. Chem. 2001, 44, 2374.
49. Xia, Y.; Mirzai, B.; Chackamannil, S.; Czamiecki, M.; Wang, S.; Clemmons, A.; Ahn, H.-S.; Boykow, G. C. Bioorg. Med. Chem. Lett. 1996, 6, 919.
50. Littke, A. F.; Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 4020.
51. For mechanistic studies, see: (a) Singh, U. K.; Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 14104.
52. (b) Alcazar-Roman, L. M.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 12905.
53. (c) Alcazar-Roman, L. M.; Hartwig, J. F.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. J. Am. Chem. Soc. 2000, 122, 4618 and references therein. Also, see ref 35.
54. For the use of alkali metal hydroxides as bases in animation chemistry, see: Kuwano, R.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2002, 67, 6479.
55. Wüllner, G.; Jänsch, H.; Kannenberg, S.; Schubert, F.; Boche, G. Chem. Commun. 1998, 1509.