Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions

Journal of the American Chemical Society

Volumn 131, Issue 39, 2009, Pages 13888-13889

  Wu, Junliang ^a   Cui, Xiuling ^a   Chen, Lianmei ^a   Jiang, Guojie ^a   Wu, Yangjie ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SPECIES; ALKENYLATION; C-H ACTIVATION; CATALYTIC PROCESS; CH-BOND ACTIVATION; CHEMICAL EQUATIONS; CROSS-COUPLINGS; HECK COUPLING; ISOQUINOLINES; N-OXIDES; PALLADIUM ACETATE; REDUCTANTS;

ACTIVATION ANALYSIS; CHEMICAL BONDS; CHEMICAL REACTIONS; OLEFINS; ORGANOMETALLICS; OXIDANTS; PALLADIUM COMPOUNDS;

PALLADIUM;

ALKENE DERIVATIVE; OXIDE; OXIDIZING AGENT; PALLADIUM ACETATE; QUINOLINE DERIVATIVE; REDUCING AGENT;

ARTICLE; CATALYSIS; CROSS COUPLING REACTION; HECK REACTION; HYDROGEN BOND;

ACRYLATES; ALKENES; CATALYSIS; CYCLIC N-OXIDES; PALLADIUM; QUINOLINES;

EID: 70349617692     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja902762a     Document Type: Article

References (34)

1. For reviews, see: (a) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
2. (b) Jia, C.; Kitamura, T.; Fujiwara, Y. Acc. Chem. Res. 2001, 34, 633.
3. (c) Shilov, A. E.; Shul'pin, G. B. Chem. Rev. 1997, 97, 2879.
4. (d) Labinger, J. A.; Bercaw, J. E. Nature 2002, 417, 507.
5. (e) Fujiwara, Y.; Jia, C. Pure Appl. Chem. 2001, 73, 319.
6. (f) Kakiuchi, F.; Murai, S. Acc. Chem. Res. 2002, 35, 826.
7. (g) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174.
8. (a) Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Angew. Chem., Int. Ed. Engl. 1997, 36, 1740.
9. (b) Bedford, R. B.; Coles, S. J.; Hursthouse, M. B.; Limmert, M. E. Angew. Chem., Int. Ed. 2003, 42, 112.
10. (c) Bedford, R. B.; Limmert, M. E. J. Org. Chem. 2003, 68, 8669.
11. (a) Kakiuchi, F.; Kan, S.; Igi, K.; Chatani, N.; Murai, S. J. Am. Chem. Soc. 2003, 125, 1698.
12. (b) Kakiuchi, F.; Matsuura, Y.; Kan, S.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 5936.
13. (c) Satoh, T.; Kametani, Y.; Terao, Y.; Miura, M.; Nomura, M. Tetrahedron Lett. 1999, 40, 5345.
14. (d) Kawatsura, M.; Hartwig, J. J. Am. Chem. Soc. 1999, 121, 1473.
15. (a) Oi, S.; Ogino, Y.; Fukita, S.; Inoue, Y. Org. Lett. 2002, 4, 1783.
16. (b) Ackermann, L. Org. Lett. 2005, 7, 3123.
17. (c) Ueura, K.; Satoh, T.; Miura, M. Org. Lett. 2005, 7, 2229.
18. (a) Kalyani, D.; Deprez, N. R.; Desai, L. V.; Sanford, M. S. J. Am. Chem. Soc. 2005, 127, 7330.
19. (b) Shabashov, D.; Daugulis, O. Org. Lett. 2005, 7, 3657.
20. (c) Zhang, Y.; Feng, J.; Li, C. J. J. Am. Chem. Soc. 2008, 130, 2900.
21. Oi, S.; Aizawa, E.; Ogino, Y.; Inoue, Y. J. Org. Chem. 2005, 70, 3113.
22. (a) Kametani, Y.; Satoh, T.; Miura, M.; Nomura, M. Tetrahedron Lett. 2000, 41, 2655.
23. (b) Shi, Z.; Li, B.; Wan, X.; Cheng, J.; Fang, Z.; Cao, B.; Qin, C.; Wang, Y. Angew. Chem., Int. Ed. 2007, 46, 5554.
24. (a) Campeau, L. C.; Rousseaux, S.; Fagnou, K. J. Am. Chem. Soc. 2005, 127, 18020.
25. (b) Leclerc, J. P.; Fagnou, K. Angew. Chem., Int. Ed. 2006, 45, 7781.
26. (c) Campeau, L. C.; Bertrand-Laperle, M.; Leclerc, J. P.; Villemure, E.; Gorelsky, S.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3266.
27. (d) Campeau, L. C.; Schipper, D. J.; Fagnou, K. J. Am. Chem. Soc. 2008, 130, 3276.
28. (e) Kanyiva, K. S.; Nakao, Y.; Hiyama, T. Angew. Chem., Int. Ed. 2007, 46, 8872.
29. (f) Cho, S. H.; Hwang, S. J.; Chang, S. J. Am. Chem. Soc. 2008, 130, 9254.
30. Pool, J.; Scott, B.; Kiplinger, J. J. Am. Chem. Soc. 2005, 127, 1338.
31. Heimgärtner, G.; Raatz, D.; Reiser, O. Tetrahedron 2005, 61, 643.
32. For the Heck reaction, see: (a) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
33. (b) Negishi, E.; Copéret, C.; Ma, S.; Liou, S.; Liu, F. Chem. Rev. 1996, 96, 365.
34. (c) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.