A novel palladium-catalyzed amination of aryl halides with amines using rac-P-phos as the ligand

Chinese Journal of Chemistry

Volumn 27, Issue 7, 2009, Pages 1382-1386

  Chen, Huansheng ^a   Wang, Quanrui ^a   Tao, Fenggang ^a  

^a FUDAN UNIVERSITY   (China)

Author keywords

Aromatic amine; Buchwald Hartwig amination; Palladium; Rac P Phos

Indexed keywords

EID: 70449356936     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.200990231     Document Type: Article

References (37)

1. Czarnik, A. W. Acc. Chem. Res. 1996, 29, 112, and references cited therein.
2. MacDiarmid, A. G. Synth. Met. 1997, 84, 27.
3. Gospodinova, N.; Terlemezyan, L. Prog. Polym. Sci. 1998, 23, 1443.
4. For recent reviews on construction of C-N bonds on the copper-mediated cross-coupling reactions, see: (a) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400.
5. Kunz, K.; Scholz, U.; Ganzer, D. Synlett 2003, 2428.
6. Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248(21-24), 2337.
7. For selected reviews, see: (a) Hartwig, J. F. Angew. Chem., Int. Ed. 1998, 37, 2046.
8. Wolfe, J. P.; Buchwald, S. L. Angew. Chem., Int. Ed. 1999, 38, 2413.
9. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
10. Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348, 23.
11. For arbitrary examples, see: (a) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
12. Burgos, C. H.; Barder, T. E.; Huang, X.; Buchwald, S. L. Angew. Chem., Int. Ed. 2006, 45, 4321.
13. Hill, L. L.; Moore, L. R.; Huang, R. C.; Craciun, R.; Vincent, A. J.; Dixon, D.; Chou, A. J.; Woltermann, C. J.; Shaughnessy, K. H. J. Org. Chem. 2006, 71, 5117.
14. For a recent explanation of the air stability of electron-rich dialkylbiaryl phosphines, see: Barder, T. E.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 5096.
15. Shi, J.; Cao, X.; Zheng, Y.; Jia, L. Acta Chim. Sinica 2007, 65, 1702 (in Chinese).
16. Shi, J.; Cao, X.; Zheng, Y.; Jia, L. Chin. J. Org. Chem. 2007, 27, 666 (in Chinese).
17. For reviews, see: Au-Yeung, T. T. L.; Chan, A. S. C. Coord. Chem. Rev. 2004, 248(21-24), 2154.
18. Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
19. Singer, R. A.; Caron, S.; McDermott, R. E.; Arpin, P.; Do, N. M. Synthesis 2003, 1727.
20. 10 Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004, 10, 2983.
21. Dai, Q.; Gao, W.; Liu, D.; Kapes, L. M.; Zhang, X. J. Org. Chem. 2006, 71, 3928.
22. Pai, C. C.; Lin, C. W.; Lin, C. C.; Chen, C. C.; Chan, A. S. C. J. Am. Chem. Soc. 2000, 122, 11513.
23. Wu, J.; Chan, A. S. C. Acc. Chem. Res. 2006, 39, 711.
24. Xie, X. X.; Zhang, T. Y.; Zhang, Z. G. J. Org. Chem. 2006, 71, 6522.
25. Martineau, D.; Gros, P.; Fort, Y. J. Org. Chem. 2004, 69, 7914.
26. Old, D. W.; Wolfe, J. P.; Buchwald, S. L.; Ohta, T. J. Org. Chem. 1984, 49, 3359.
27. Zhang, H.; Cai, Q.; Ma, D. J. Org. Chem. 2005, 70, 5164.
28. Lane, B. S.; Sames, D. Org. Lett. 2004, 6, 2897.
29. Spagnolo, P.; Zanirato, P. Tetrahedron Lett. 1987, 28, 961.
30. Pachter, I. J.; Kloetzel, M. C. J. Am. Chem. Soc. 1952, 74, 1321.
31. Kremer, C. B.; Meltsner, M.; Greenstein, L. J. Am. Chem. Soc. 1939, 61, 2552.
32. Anderson, K. W.; Mendez-Perez, M.; Priego, J.; Buchwald, S. L. J. Org. Chem. 2003, 68, 9563.
33. Urgaonkar, S.; Verkade, J. G. Adv. Synth. Catal. 2004, 346, 611.
34. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1998, 120, 9722.
35. Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054.
36. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 61, 7240.
37. Krein, D. M.; Lowary, T. L. J. Org. Chem. 2002, 67, 4965.