Palladium-catalyzed amination of aryl and heteroaryl tosylates at room temperature

Journal of the American Chemical Society

Volumn 130, Issue 42, 2008, Pages 13848-13849

  Ogata, Tokutaro ^a   Hartwig, John F ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

PALLADIUM; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; TOLUENESULFONIC ACID DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION KINETICS; HYDROLYSIS; OXIDATION KINETICS; REDUCTION KINETICS; ROOM TEMPERATURE; TEMPERATURE SENSITIVITY;

AMINATION; AMINES; CATALYSIS; IMINES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; PALLADIUM; STEREOISOMERISM; TEMPERATURE; TOSYL COMPOUNDS;

EID: 54249087134     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja805810p     Document Type: Article

References (30)

1. (a) Hartwig, J. F. Acc. Chem. Res. published online, Aug. 6, 2008, http://dx.doi.org/10.1021/ar800098p.
2. (b) Hartwig, J. F. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; pp 107.
3. (c) Hartwig, J. F. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E., Ed.; Wiley-Interscience: New York, 2002; pp 1051.
4. (d) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
5. For a recent review of aminations conducted with o-biaryl dialkylphosphine ligands, see: Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338.
6. For a recent report of aminations conducted with N-heterocyclic carbenes, see: Marion, N.; Navarro, O.; Mei, J.; Stevens, E. D.; Scott, N. M.; Nolan, S. P. J. Am. Chem. Soc. 2006, 128, 4101.
7. (a) Tang, Z.-Y.; Hu, Q.-S. J. Am. Chem. Soc. 2004, 126, 3058.
8. (b) Tang, Z.-Y.; Spinella, S.; Hu, Q.-S. Tetrahedron Lett. 2006, 47, 2427.
9. (c) Kobayashi, Y.; Mizojiri, R. Tetrahedron Lett. 1996, 37, 8531.
10. (d) Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364.
11. (e) Fürstner, A.; Leitner, A.; Mendez, M.; Krause, H. J. Am. Chem. Soc. 2002, 124, 13856.
12. (f) Fürstner, A.; Leitner, A. Angew. Chem., Int. Ed. 2002, 41, 609.
13. (a) Roy, A. H.; Hartwig, J. F. J. Am. Chem. Soc. 2003, 125, 8704.
14. For two examples of the amination of aryl tosylates at elevated temperatures with a related catalyst, see: (b) Hamann, B. C.; Hartwig, J. F. J. Am. Chem. Soc. 1998, 120, 7369.
15. For recent work on the amination of aryl mesylates, at elevated temperatures, see: (c) So, C. M.; Zhou, Z.; Lau, C. P.; Kwong, F. Y. Angew. Chem., Int. Ed. 2008, 47, 6402.
16. Ligand 3 is commercially available from Solvias and Strem.
17. (a) Paul, F.; Patt, J.; Hartwig, J. F. Organometallics 1995, 14, 3030.
18. (b) Böhm, V. P. W.; Herrmann, W. A. Chem. - Eur. J. 2001, 7, 4191.
19. Dai, C.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 2719.
20. Complex 2 is commercially available from Johnson-Matthey and Strem Chemicals (#46-0262).
21. 31P NMR spectroscopy.
22. Naber, J. R.; Buchwald, S. L. Adv. Synth. Catal. 2008, 350, 957.
23. For reactions of activated aryl tosylates with 0.5 mol % palladium, see refs 13 and 14.
24. Ackermann, L.; Althammer, A. Org. Lett. 2006, 8, 3457.
25. Zhang, L.; Meng, T.; Wu, J. J. Org. Chem. 2007, 72, 9346.
26. Shelby, Q.; Kataoka, N.; Mann, G.; Hartwig, J. F. J. Am. Chem. Soc. 2000, 122, 10718.
27. Huang, X.; Anderson, K. W.; Zim. D.; Jiang, L.; Klapars. A.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 6653.
28. 2 and 5 mol % X-phos at 110°C for 18 h occurred to 84% conversion.
29. Åhman, J.; Buchwald, S. L. Tetrahedron Lett. 1997, 38, 6363.
30. Nguyen, H. N.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2003, 125, 11818.