Catalytic and highly regioselective cross-coupling of aromatic C-H substrates

Journal of the American Chemical Society

Volumn 129, Issue 39, 2007, Pages 11904-11905

  Hull, Kami L ^a   Sanford, Melanie S ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; CARBON; HYDROGEN; PALLADIUM;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; LIGAND BINDING; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

BENZENE DERIVATIVES; CATALYSIS; HETEROCYCLIC COMPOUNDS; OXIDATION-REDUCTION; PALLADIUM; PYRAZOLES; PYRIDINES; PYRIMIDINES; QUINOLINES;

EID: 34848899222     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja074395z     Document Type: Article

References (21)

1. Hassan, J.; Sevignon, M.; Gozzi, C.; Schulz, E.; Lemaire, M. Chem. Rev. 2002, 102, 1359 and references therein.
2. 6 oxidative coupling, see: (a) van Helden, R.; Verberg, G. Recl. Trav. Chim. Pays-Bas 1965, 84, 1263.
3. (b) Burton, H. A.; Kozhevnikov, I. V. J. Mol. Catal. A 2002, 185, 285.
4. Takahashi, M.; Masui, K.; Sekiguchi, H.; Kobayashi, N.; Mori, A.; Funahashi, M.; Tamaoki, N. J. Am. Chem. Soc. 2006, 128, 10930.
5. Hull, K. L.; Lanni, E. L.; Sanford, M. S. J. Am. Chem. Soc. 2006, 128, 14047.
6. For recent elegant advances in Pd-catalyzed oxidative heterocoupling, see: (a) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
7. (b) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
8. (c) Li, R.; Jiang, L.; Lu, W. Organometallics 2006, 25, 5973.
9. For oxidative C-H cross-coupling with Cu, see: Li, X. L.; Hewgley, J. B.; Mulrooney, C. A.; Yang, J. M.; Kozlowski, M. C. J. Org. Chem. 2003, 68, 5500.
10. Dunina, V. V.; Zalevskaya, O. A.; Potapov, V. M. Russ. Chem. Rev. 1988, 57, 250.
11. Ryabov, A. D. Inorg. Chem. 1987, 26, 1252.
12. II that is promoted by BQ, see: Chen, X.; Li, J.-J.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 78.
13. II/DMSO catalysts in oxidation reactions, see: Steinhoff, B. A.; Stahl, S. S. J. Am. Chem. Soc. 2006, 128, 4348 and references therein.
14. (a) Maleczka, R. E.; Shi, F.; Holmes, D.; Smith, M. R. J. Am. Chem. Soc. 2003, 125, 7792.
15. (b) Ishiyama, T.; Takagi, J.; Ishida, K.; Miyaura, N.; Anastasi, N. R.; Hartwig, J. F. J. Am. Chem. Soc. 2002, 124, 390.
16. (c) Cho, J.-Y.; Iverson, C. N.; Smith, M. R. J. Am. Chem. Soc. 2000, 122, 12868.
17. II, see: (a) Älbeniz, A. C.; Espinet, P.; Martin-Ruiz, B. Chem. - Eur. J. 2001, 7, 2481.
18. (b) Backvall, J.-E.; Bystrom, S. E.; Nordberg, R. E. J. Org. Chem. 1984, 49, 4619.
19. This is believed to be due to a combination of steric and electronic factors. Studies are underway to definitively establish the role that each plays in these transformations.
20. For example, see: Jia, C.; Lu, W.; Oyamada, J.; Kitamura, T.; Matsuda, K.; Irie, M.; Fujiwara, Y. J. Am. Chem. Soc. 2000, 122, 7252.
21. Lafrance, M.; Rowley, C. N.; Woo, T. K.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 8754.