[(CyPF-Bu)PdCI2]: An air-stable, one-component, highly efficient catalyst for amination of heteroaryl and aryl halides

Organic Letters

Volumn 10, Issue 18, 2008, Pages 4109-4112

  Shen, Qilong ^a,b   Hartwig, John F ^a,b  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HALOGEN; ORGANOMETALLIC COMPOUND; PALLADIUM;

AIR; AMINATION; ARTICLE; CATALYSIS; CHEMISTRY;

AIR; AMINATION; CATALYSIS; HALOGENS; ORGANOMETALLIC COMPOUNDS; PALLADIUM;

EID: 55949111083     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol801615u     Document Type: Article

References (42)

1. (a) Hartwig, J. F.; Shekhar, S.; Shen, Q.; Barrios-Landeros, F. In Chemistry of Anilines; Rappoport, Z., Ed.; John Wiley & Sons Ltd.: Chichester, UK, 2007; Vol. 1, p 455.
2. (b) Hartwig, J. F. In Modern Arene Chemistry; Austruc, C., Ed.; Wiley-VCH: Weinheim, 2002; p 107.
3. (c) Hartwig, J. F. Handbook of Organopalladium Chemistry for Organic Synthesis; Negoshi, E., Ed.; Wiley-Intescience: New York, 2002; p 1051.
4. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 279, 131.
5. (e) Belfield, A. J.; Brown, G. R.; Foubister, A. J.; Ratcliffe, P. D. Tetrahedron 1999, 55, 13285.
6. (f) Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125.
7. (a) Buchwald, S. L.; Mauger, C.; Mignani, G.; Scholz, U. Adv. Synth. Catal. 2006, 348, 23.
8. (b) King, A. O.; Yasuda, N. In Organometallics in Process Chemistry; Larsen, R. D., Ed.; Springer: Berlin, 2004; p 205.
9. Shen, Q.; Shekhar, S.; Stambuli, J. P.; Hartwig, J. F. Angew. Chem., Int. Ed. 2005, 44, 1371.
10. Schlosser, M. Organometallics in Synthesis: A Manual, 2nd ed.; John Wiley & Sons, Ltd.: Chichester, 2002.
11. (a) Hooper, M. W.; Utsunomiya, M.; Hartwig, J. F. J. Org. Chem. 2003, 68, 2861.
12. (b) Yin, J.; Zhao, M. M.; Huffman, M. A.; McNamara, J. M. Org. Lett. 2002, 4, 3481.
13. (c) Jonckers, T. H. M.; Maes, B. U. W.; Lemiere, G. L. F.; Dommisse, R. Tetrahedron 2001, 57, 7027.
14. (d) Maes, B. U. W.; Loones, K. T. J.; Lemiere, G. L. F.; Dommisse, R. A. Synlett 2003, 1822.
15. (e) Burton, G.; Cao, P.; Li, G.; Rivero, R. Org. Lett. 2003, 5, 4373.
16. (f) Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240.
17. (g) Ji, J.; Li, T.; Bunnelle, W. H. Org. Lett. 2003, 5, 4611.
18. (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1996, 61, 1133.
19. (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
20. (c) Ali, M. H.; Buchwald, S. L. J. Org. Chem. 2001, 66, 2560.
21. (d) Parrot, I.; Ritter. G.; Wermuth, C. G.; Hibert, M. Synlett 2002, 1123.
22. (a) Littke, A. F.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 4176.
23. (b) Stambuli, J. P.; Kuwano, R.; Hartwig, J. F. Angew. Chem., Int. Ed. 2002, 41, 4746.
24. (c) Wolfe, J. P.; Tomori, H.; Sadighi, J. P.; Yin, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1158.
25. (d) Huang, X.; Anderson, K. W.; Zim, D.; Jiang, L.; Klapars, A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
26. (e) Kataoka, N.; Shelby, Q.; Stambuli, J. P.; Hartwig, J. F. J. Org. Chem. 2002, 67, 5553.
27. (f) Urgaonkar, S.; Xu, J.-H.; Verkade, J. G. J. Org. Chem. 2003, 68, 8416.
28. (g) Viciu, M. S.; Kissling, R. M.; Stevens, E. D.; Nolan, S. P. Org. Lett. 2002, 4, 2229.
29. (h) Grasa, G. A.; Viciu, M. S.; Huang, J.; Nolan, S. P. J. Org. Chem. 2001, 66, 7729.
30. (i) Li. G. Y. Angew. Chem., Int. Ed. 2001, 40, 1513.
31. (j) Rataboul, F.; Zapf, A.; Jackstell, R.; Harkal, S.; Riermeier, T.; Monsees, A.; Dingerdissen, U.; Beller, M. Chem. Eur. J. 2004, 10, 2983.
32. Stauffer, S. R.; Lee, S.; Stambuli, J. P.; Hauck, S. I.; Hartwig, J. F. Org. Lett. 2000, 2, 1423.
33. Louie, J.; Hartwig, J. F. Tetrahedron Lett. 1995, 36, 3609.
34. (a) Harris, M. C.; Huang, X.; Buchwald, S. L. Org. Lett. 2002, 4, 2885.
35. (b) Urgaonkar, S.; Verkade, J. G. Adv. Synth. Catal. 2004, 346, 611.
36. (a) Wolfe, J. P.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6359.
37. (b) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144.
38. (c) Lee, S.; Jorgensen, M.; Hartwig, J. F. Org. Lett. 2001, 3, 2729.
39. (a) Nishiyama, M.; Yamamoto, T.; Koie, Y. Tetrahedron Lett. 1998, 39, 617.
40. (b) Navarro, O.; Marion, N.; Mei, J.; Nolan, S. P. Chem. - Eur. J. 2006, 12, 5142.
41. (c) Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101.
42. (d) Marion, N.; Ecarnot, E. C.; Navarro, O.; Amoroso, D.; Bell, A.; Nolan, S. P. J. Org. Chem. 2006, 71, 3816.