Carbon-nitrogen bond formation involving well-defined aryl-copper(III) complexes

Journal of the American Chemical Society

Volumn 130, Issue 29, 2008, Pages 9196-9197

  Huffman, Lauren M ^a   Stahl, Shannon S ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBON; COPPER COMPLEX; DIPYRONE; NITROGEN; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CORRELATION ANALYSIS; KINETICS; PKA; SPECTROSCOPY;

AMIDES; AMINES; COPPER; HYDROCARBONS, AROMATIC; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLIC COMPOUNDS; PHTHALIMIDES; PYRIDONES;

EID: 47749101331     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja802123p     Document Type: Article

References (24)

1. Ullmann, F. Ber. Dtsch. Chem. Ges. 1903, 36, 2382-2384.
2. Cu-mediated coupling reactions continue to be the focus of extensive interest. For reviews, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
3. (b) Hassan, J.; Sévignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359-1469.
4. (c) Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400-5449.
5. Krause, N. Modern Organocopper Chemistry; Wiley-VCH: Weinheim, Germany, 2002.
6. For representative examples, see: (a) Willert-Porada, M. A.; Burton, D. J.; Baenziger, N. C. J. Chem. Soc., Chem. Commun. 1989, 1633-1634.
7. (b) Naumann, D.; Roy, T.; Tebbe, K.-F.; Crump, W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1482-1483.
8. (c) Furuta, H.; Maeda, H.; Osuka, A. J. Am. Chem. Soc. 2000, 122, 803-807.
9. (d) Ribas, X.; Jackson, D. A.; Donnadieu, B.; Mahía, J.; Parella, T.; Xifra, R.; Hedman, B.; Hodgson, K. O.; Llobet, A.; Stack, T. D. P. Angew. Chem., Int. Ed. 2002, 41, 2991-2994.
10. (e) Santo, R.; Miyamoto, R.; Tanaka, R.; Nishioka, T.; Sato, K.; Toyota, K.; Obata, M.; Yano, S.; Kinoshita, I.; Ichimura, A.; Takui, T. Angew. Chem., Int. Ed. 2006, 45, 7611-7614.
11. (a) Bertz, S. H.; Cope, S.; Murphy, M.; Ogle, C. A.; Taylor, B. J. J. Am. Chem. Soc. 2007, 129, 7208-7209.
12. (b) Hu, H.; Snyder, J. P. J. Am. Chem. Soc. 2007, 129, 7210-7211.
13. (c) Bertz, S. H.; Cope, S.; Dorton, D.; Murphy, M.; Ogle, C. A. Angew. Chem., Int. Ed. 2007, 46, 7082-7085.
14. (d) Gartner, T.; Henze, W.; Gschwind, R. M. J. Am. Chem. Soc. 2007, 129, 11362-11363.
15. For recent development of efficient Cu-catalyzed C-N coupling reactions, see the following leading references: (a) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
16. (b) Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8742-8743.
17. In addition to aryl-halide cross-coupling reactions (ref 6), Cu-catalyzed oxidative C-N coupling reactions aryl boronic acids have been reported: (a) Chan, D. M. T.; Monaco, K. L.; Wang, R.-P.; Winters, M. P. Tetrahedron Lett. 1998, 39, 2933-2936.
18. (b) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Winters, M. P.; Chan, D. M. T.; Combs, A. Tetrahedron Lett. 1998, 39, 2941-2944.
19. Xifra, R.; Ribas, X.; Llobet, A.; Poater, A.; Duran, M.; Sola, M.; Stack, T. D. P.; Benet-Buchholz, J.; Donnadieu, B.; Mahia, J.; Parella, T. Chem. - Eur. J. 2005, 11, 5146-5156.
20. 3CN, 24°C.
21. See section 1 of the Supporting Information for further details.
22. In acetonitrile at 25°C, the pyridone tautomer is more stable than 2-hydroxypyridine by approx 3 kcal/mol: Frank, J.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 2 1976, 1428-1431.
23. Mechanistic evidence suggests the nitrogen nucleophile coordinates to the Cu center before C-N bond formation in Cu-catalyzed cross-coupling reactions. See, for example: Strieter, E. R.; Blackmond, D. G.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 4120-4121.
24. 2) react more rapidly than benzamide (see section 2 of the Supporting Information for details).