Synthesis of polycyclic benzonitriles via a one-pot aryl alkylation/cyanation reaction

Journal of the American Chemical Society

Volumn 128, Issue 45, 2006, Pages 14436-14437

  Mariampillai, Brian ^a   Alberico, Dino ^a   Bidau, Valérie ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

BENZONITRILE; PALLADIUM; POLYCYCLIC HYDROCARBON;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL MODIFICATION; CYANATION; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 33750967058     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja064742p     Document Type: Article

References (31)

1. For selected articles on palladium-catalyzed cyanation, see (a) Sundermeier, M.; Zapf, A.; Beller, M. Angew. Chem., Int. Ed. 2003, 42, 1661-1664.
2. (b) Sundermeier, M.; Zapf, A.; Mutyala, S.; Baumann, W.; Sans, J.; Weiss, S.; Beller, M. Chem.-Eur. J. 2003, 9, 1828-1836.
3. (c) Schareina, T.; Zapf. A.; Beller, M. Chem. Commun. 2004, 1388-1389.
4. (d) Anderson, B. A.; Bell, E. C.; Ginah, F. O.; Harn, N. K.; Pagh, L. M.; Wepsiec, J. P. J. Org. Chem. 1998, 63, 8224-8228.
5. (e) Sundermeier, M.; Mutyala, S.; Zapf, A.; Spannenberg, A.; Beller, M. J. Organomet. Chem. 2003, 684, 50-55.
6. (f) Schareina, T.; Zapf, A.; Beller, M.; J. Organom. Chem. 2004, 689, 4576-4583.
7. (g) Yang, C.; Williams, J. M. Org. Lett. 2004, 6, 2837-2840.
8. (h) Marcantonio, K. M.; Frey, L. F.; Liu, Y.; Chen, Y.; Strine, J.; Phenix, B.; Wallace, D. J.; Chen, C. Org. Lett. 2004, 6, 3723-3725.
9. (i) Grossman, O.; Gelman, D. Org. Lett. 2006, 8, 1189-1191.
10. (j) Weissman, S. A.; Zewge, D.; Chen, C. J. Org. Chem. 2005, 70, 1508-1510.
11. For tandem palladium-catalyzed cyanation reactions, see (a) Larock, R. C.; Takagi, K.; Hershberger, S. S.; Mitchell, M. A. Tetrahedron Lett. 1981, 22, 5231-5234.
12. (b) Larock, R. C.; Hershberger, S. S.; Takagi, K.; Mitchell, M. A. J. Org. Chem. 1986, 51, 2450-2457.
13. (c) Torii, S.; Okumoto, H.; Ozaki, S.; Nakayasu, S.; Kotani, T. Tetrahedron Lett. 1990, 31, 5319-5322.
14. (d) Torii, S.; Okumoto, H.; Ozaki, S.; Nakayasu, S.; Tadokoro, T.; Kotani, T. Tetrahedron Lett. 1992, 33, 3499-3502.
15. (e) Grigg, R.; Santhakumar, V.; Sridharan, V. Tetrahedron Lett. 1993, 34, 3163-3164.
16. (f) Nakamura, H.; Shibata, H.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 2911-2914.
17. (g) Tanaka, M. Bull. Chem. Soc. Jpn. 1981, 54, 637-638.
18. (h) Nozaki, K.; Sato, N.; Takaya, H. J. Org. Chem. 1994, 59, 2679-2681.
19. For previous work by our group on norbornene-mediated ortho-alkylation chemistry, see (a) Lautens, M.; Alberico, D.; Bressy, C.; Fang, Y.-Q.; Mariampillai, B.; Wilhelm, T. Pure Appl. Chem. 2006, 78, 351-361.
20. (b) Martins, A.; Marquardt, U.; Kasravi, N.; Alberico, D.; Lautens, M. J. Org. Chem. 2006, 71, 4937-4942.
21. (c) Martins, A.; Alberico, D.; Lautens, M. Org. Lett. 2006, 8, 4827-4829.
22. (d) Blaszykowski, C.; Aktoudianakis, E.; Bressy, C.; Alberico, D.; Lautens, M. Org. Lett. 2006, 8, 2043-2045.
23. (e) Alberico, D.; Paquin, J.-F.; Lautens, M. Tetrahedron 2005, 61, 6283-6296.
24. (f) Pache, S.; Lautens, M. Org. Lett. 2003, 5, 4827-4830.
25. For recent work by Catellani and co-workers on norbornene-mediated ortho-functionalization chemistry, see (a) Ferraccioli, R.; Carenzi, D.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2006, 128, 722-723.
26. (b) Catellani, M.; Motti, E.; Faccini, F.; Ferraccioli, R. Pure and Appl. Chem. 2005, 77, 1243-1248.
27. (c) Deledda, S.; Motti, E.; Catellani, M. Can. J. Chem. 2005, 83, 741-747.
28. (d) Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78-79.
29. (e) Catellani, M. Synlett 2003, 298-313.
30. The reaction could also be carried out in a sealed tube at 150 °C using conventional heating for 4000 seconds to give 2 in a 77% yield.
31. Alterman, M.; Hallberg, A. J. Org. Chem. 2000, 65, 7984-7989.