Ligand effects in the synthesis of N-heterocycles by intramolecular Heck reactions

Journal of Organic Chemistry

Volumn 71, Issue 4, 2006, Pages 1732-1735

  Cropper, Emma L ^a   White, Andrew J P ^a   Ford, Agnes ^a,b   Hii, King Kuok ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOLACTAMS; DIHYDROPHENANTHRIDINE PRODUCT;

CONFORMATIONS; CRYSTALLOGRAPHY; X RAY ANALYSIS;

SYNTHESIS (CHEMICAL);

HETEROCYCLIC COMPOUND;

ARTICLE; CHEMICAL BOND; CYCLIZATION; HECK REACTION; ISOMERIZATION; MOLECULAR STABILITY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BENZENE DERIVATIVES; CRYSTALLOGRAPHY, X-RAY; HETEROCYCLIC COMPOUNDS; LACTAMS; LIGANDS; MOLECULAR CONFORMATION; NITROGEN;

EID: 33644508323     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0522660     Document Type: Article

References (36)

1. (a) Link, J. T. Org. React. (N.Y.) 2002, 60, 157.
2. (b) Dyker, G. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley: New York, 2002; Vol. 1.
3. Jeffery, T. Tetrahedron 1996, 52, 10113.
4. Rigby, J. H.; Hughes, R. C.; Heeg, M. J. J. Am. Chem. Soc. 1995, 117, 7834.
5. Lemaire-Audoire, S.; Savignac, M.; Dupuis, C.; Genet, J. P. Tetrahedron Lett. 1996, 37, 2003.
6. (a) Di Fabio, R.; Micheli, F.; Baraldi, D.; Bertani, B.; Conti, N.; Dal Forno, G.; Feriani, A.; Donati, D.; Marchioro, C.; Messen, T.; Missio, A.; Pasquarello, A.; Pentassuglia, G.; Pizzi, D. A.; Provera, S.; Quaglia, A. M.; Sabbatini, F. M. Farmaco 2003, 58, 723.
7. (b) Hayashi, M.; Sai, H.; Horikawa, H. Heterocycles 1998, 48, 1331.
8. (a) Arnold, L. A.; Luo, W.; Guy, R. K. Org. Lett. 2004, 6, 3005.
9. (b) Gibson, S. E.; Jones, J. O.; Kalindjinan, S. B.; Knight, J. D.; Steed, J. W.; Tozer, M. J. J. Chem. Soc., Chem. Commun. 2002, 1938.
10. (c) Alcaide, B.; Polanco, C.; Sierra, M. A. Eur. J. Org. Chem. 1998, 2913.
11. (d) Gibson, S. E.; Middleton, R. J. J. Chem. Soc., Chem. Commun. 1995, 1743.
12. For example, see: (a) Santos, L. S.; Pilli, R. A. Synthesis 2002, 87.
13. (b) Tietze, L. F.; Sommer, K. M.; Schneider, G.; Tapolzsányi, P.; Wölfling, J.; Müller, P.; Noltemeyer, M.; Terlau, H. Synlett 2003, 1494.
14. Qadir, M.; Cobb, J.; Sheldrake, P. W.; Whittall, N.; White, A. J. P.; Hu, K. K.; Horton, P. N.; Hursthouse, M. B. J. Org. Chem. 2005, 70, 1545.
15. (a) Kaoudi, T.; Quiclet-Sire, B.; Seguin, S.; Zard, S. Z. Angew. Chem., Int. Ed. 2000, 39, 731.
16. (b) Clark, A. J.; Jones, K.; McCarthy, C.; Storey, J. M. D. Tetrahedron Lett. 1991, 32, 2829.
17. Mori, M.; Hashimoto, Y.; Ban, Y. Tetrahedron Lett. 1980, 21, 631.
18. Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
19. For a review on intramolecular Heck reactions involving formal anti-elimination processes, see: Ikeda, M.; El Bialy, S. A. A.; Yakura, T. Heterocycles 1999, 51, 1957.
20. The reversibility of β-hydride migration and the convergence of the intermediates rules out the determination of reaction pathways by isotopic (deuterium) labeling.
21. CCDC reference code YUFFOU; see: Gupta, V. K.; Goswami, K. N.; Yadava, V. B. S.; Gupta, D. K.; Bhutani, K. K. Z. Kristallogr. 1995, 210, 154.
22. CCDC reference codes VABGUA, VABHAH, and COPTOQ: (a) Yoshida, K.; Nakajima, S.; Ohnuma, T.; Ban, Y.; Shibasaki, M.; Aoe, K.; Date, T. J. Org. Chem. 1988, 53, 5355.
23. (b) Oda, K.; Ohnuma, T.; Ban, Y.; Aoe, K. J. Am. Chem. Soc. 1984, 106, 5378.
24. -1 (ref 8).
25. -1: Qadir, M.; Cobb, J.; White, A. J. P.; Sheldrake, P. W.; Whittall, N.; Hu, K. K.; Horton, P. N.; Hursthouse, M. B. J. Org. Chem. 2005, 70, 1552.
26. Christmann, U.; Vilar, R. Angew. Chem., Int. Ed. 2005, 44, 366 and references therein.
27. (a) Littke, A. F.; Fu, G. C. J. Am. Chem. Soc. 2001, 123, 6989.
28. (b) Stambuli, J. P.; Stauffer, S. R.; Shaughnessy, K. H.; Hartwig, J. F. J. Am. Chem. Soc. 2001, 123, 2677.
29. Palladium hydride can be generated through β-hydride elimination of a coordinated triethylamine. The choice of base has been found to affect the generation and stability of palladium hydride species; see: Hills, I. D.; Fu, G. C. J. Am. Chem. Soc. 2004, 126, 13176.
30. Suzuki, K.; Ohmori, K. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., de Meijere, A., Eds.; Wiley: New York, 2002; Vol. 1.
31. Similar "Heck-type" biaryl coupling was effected by employing thallium and silver salts; see: (a) Grigg, R.; Savic, V.; Tambyrajah, V. Tetrahedron Lett. 2000, 41, 3003.
32. (b) Harayama, T.; Akiyama, T.; Kawano, K. Chem. Pharm. Bull. 1996, 44, 1634.
33. By adopting Jeffrey's conditions, see: (c) Garden, S. J.; Torres, J. C.; Pinto, A. C. J. Braz. Chem. Soc. 2000, 11, 441.
34. (d) Gómez-Lor, B.; Echavarren, A. M. Org. Lett. 2004, 6, 2993.
35. Li, W. R.; Lin, Y. S.; Hsu, N. M. J. Comb. Chem. 2001, 3, 634.
36. Kaslow, C. E.; Cook, D. J. J. Am. Chem. Soc. 1945, 67, 1969.