Improving catalyst scope: Use of multiple aniline substrates to optimize a palladium-catalyzed bisdiene cyclization

Organic Letters

Volumn 6, Issue 18, 2004, Pages 3099-3102

  Takacs, James M ^a   Han, Jianxin ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; PALLADIUM;

ARTICLE; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; REACTION ANALYSIS; STEREOSPECIFICITY; SUBSTITUTION REACTION;

ALKENES; ANILINE COMPOUNDS; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; PALLADIUM;

EID: 4544272757     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0488791     Document Type: Article

References (23)

1. Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662.
2. (b) Poli, G.; Giambastiani, G.; Heumann, A. Tetrahedron 2000, 56, 5959-5989.
3. Takacs, J. M.; Schroeder, S. D.; Han, J.; Gifford, M.; Jiang, X.-t.; Saleh, T.; Vayalakkada, S.; Yap. A. H. Org. Lett. 2003, 5, 3595-3598.
4. (b) Takacs, J. M.; Leonov, A. P. Org. Lett. 2003, 5, 4317-4320.
5. Palencia, H.; Garcia-Jimenez, F.; Takacs, J. M. Tetrahedron Lett. 2004, 45, 3849-3853.
6. Takacs, J. M. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., Ed.; John Wiley & Sons: New York, 2002; Vol. 1, pp 1579-1633.
7. Takahashi, S.; Shibano, T.; Hagihara, N. Bull. Chem. Soc. Jpn. 1968, 41, 454-460.
8. (b) Dzhemilev, U. M.; Tolstikov, G. A.; Telin, A. G.; Dolomatov, M. Y.; Galkin, E. G.; Tolstikov, G. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1980, 163-167.
9. (c) Zakharkin, L. I.; Petrushkiria, E. A. Izv. Akad. Nauk SSSR, Ser. Khim. 1986, 1344-1347.
10. (d) Viciu, M. S.; Zinn, F. K.; Stevens, E. D.; Nolan, S. P. Organometallics 2003, 22, 3175-3177.
11. Dzhemilev, U. M.; Sirazova, M. M.; Kunakova, R. V.; Panasenko, A. A.; Khalilov, L. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 372-376.
12. Dzhemilev, U. M.; Fakhretdinov, R. N.; Safuanova, R. M. Izv. Akad. Nauk SSSR, Ser. Khim. 1985, 2098-2101.
13. Jolly, P. W.; Mynott, R.; Raspel, B.: Schick, K. P. Organometallics 1986, 5, 473-481.
14. All reactions were run at 65°C for 4 h. The 4 h reaction time is arbitrary but selected to favor catalyst systems with higher turnover frequency, a key component of catalyst efficiency. The yield is determined by HPLC analysis of an aliquot taken from the crude reaction mixture.
15. See a discussion of the related nickel-catalyzed reactions of 1,3-dienes: Tobisch, S.; Ziegler, T. J. Am. Chem. Soc. 2002, 124, 13290-13301.
16. (a) Dahmen, S.; Brase, S. Synthesis 2001, 1431-1449.
17. (b) de Vries, J. G.; de Vries, A. H. M. Eur. J. Org. Chem. 2003, 799-811.
18. (c) Reetz, M. T. In Comprehensive Coordination Chemistry II; McCleverty, J. A., Meyer, T. J., Eds.; Elsevier Pergamon: Boston, 2004; Vol. 9, pp 509-548.
19. (a) Maddock, S. M.; Finn, M. G. Organometallics 2000, 19, 2684-2689.
20. (b) Basato, M.; Crociani, L.; Benvenuti, F.; Galletti, A. M. R.; Sbrana, G. J. Mol. Catal. A: Chem. 1999, 145, 313-316.
21. Chalk, A. J.; Magennis, S. A. Ann. N. Y. Acad. Sci. 1980, 333, 286-301.
22. Rodriguez, A.; Nomen, M.; Spur, B. W.; Godfroid, J.-J.; Lee, T. H. Eur. J. Org. Chem. 2000, 2991-3000.
23. All reactions were run in toluene at 65°C for 4 h. Approximately 20% of the combinations were run in duplicate, and from another 20% two aliquots were removed and analyzed separately as control experiments.