Palladium-catalyzed chloroimination of imidoyl chlorides to a triple bond: An intramolecular reaction leading to 4-chloroquinolines

Organic Letters

Volumn 10, Issue 13, 2008, Pages 2657-2659

  Isobe, Akira ^a   Takagi, Jun ^a   Katagiri, Toshimasa ^a   Uneyama, Kenji ^a  

^a OKAYAMA UNIVERSITY   (Japan)

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Indexed keywords

EID: 49049107857     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800512m     Document Type: Article

References (26)

1. (a) Negishi, E.; Meijere, A. D.; Bäckvall, J. E.; Cacchi, S.; Hayashi, T.; Ito, Y.; Kosugi, M.; Murahashi, S. I.; Oshima, K.; Yamamoto, Y. Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002; Vols. 1 and 2.
2. (b) Li, J. J.; Gribble, G. W. Tetrahedron Organic Chemistry Series 20: Palladium in Heterocyclic Chemistry: A Guide for the Synthetic Chemist; Pergamon: Amsterdam, The Netherlands, 2000.
3. (a) Wiger, G.; Albelo, G.; Rettig, M. F. J. Chem. Soc., Dalton 1974, 2242.
4. (b) Wipke, W. T.; Goeke, G. L. J. Am. Chem. Soc. 1974, 93, 4244.
5. (c) Mann, B. E.; Bailey, P. M.; Maitlis, P. M. J. Am. Chem. Soc. 1975, 97, 1275.
6. (d) Kaneda, K.; Uchiyama, T.; Fujiwara, Y.; Imanaka, T.; Teranishi, S. J. Org. Chem. 1979, 44, 55.
7. (e) Ma, S.; Lu, X. J. Chem. Soc., Chem. Commun. 1990, 733.
8. (f) Ma, S.; Lu, X. J. Org. Chem. 1991, 51, 5120.
9. (g) Ma, S.; Zhu, G.; Lu, X. J. Org. Chem. 1993, 58, 3692.
10. (h) Bäckvall, J.-E.; Nilsson, Y. I. M.; Andersson, P. G.; Gatti, R. G. P.; Wu, J. Tetrahedron Lett. 1994, 35, 5713.
11. (i) Bäckvall, J.-E.; Nilsson, Y. I. M.; Gatti, R. G. P. Organometallics 1995, 14, 4242.
12. (j) Ji, J.; Wang, Z.; Lu, X. Organometallics 1996, 15, 2821.
13. (k) Huang, X.; Sun, A. J. Org. Chem. 2000, 65, 6561.
14. (l) Lu, X. In Handbook of Organopalladium Chemistry for Organic Synthesis; Wiley-Interscience: New York, 2002; Vol. 2, p 2267.
15. (m) Ma, S.; Wu, B.; Zhao, S. Org. Lett. 2003, 5, 4429.
16. (n) Zhu, G.; Zhang, Z. J. Org. Chem. 2005, 70, 3339.
17. (a) Kokubo, K.; Matsumasa, K.; Miura, M.; Nomura, M. J. Org. Chem. 1996, 61, 6941.
18. (b) Hua, R.; Shimada, S.; Tanaka, M. J. Am. Chem. Soc. 1998, 120, 12365.
19. (c) Sugihara, T.; Satoh, T.; Miura, M.; Nomura, M. Adv. Synth. Catal 2004, 346, 1765.
20. (d) Hua, R.; Onozawa, S.; Tanaka, M. Chem. Eur. J. 2005, 11, 3621.
21. (e) Kashiwabara, T.; Kataoka, K.; Hua, R.; Shimada, S.; Tanaka, M. Org. Lett. 2005, 7, 2241.
22. See the Supporting Information [Spectroscopic Data and Experimental methods for 4-chloro-2-polyfluoroalkyl quinolines and the substrates].
23. Schlosser, M.; Cottet, F.; Heiss, C.; Lefebvre, O.; Marull, M.; Masson, E.; Scopelliti, R. Eur. J. Org. Chem. 2006, 729.
24. (a) Uneyama, K.; Watanabe, H. Tetrahedron Lett. 1991, 32, 1459.
25. (b) Watanabe, H.; Hashizume, Y.; Uneyama, K. Tetrahedron Lett. 1992, 33, 4333.
26. (c) Amii, H.; Kishikawa, Y.; Kageyama, K.; Uneyama, K. J. Org. Chem. 2000, 65, 3404.