A convergent synthesis of polysubstituted aromatic nitriles via palladium-catalyzed C-H functionalization

Journal of the American Chemical Society

Volumn 129, Issue 49, 2007, Pages 15372-15379

  Mariampillai, Brian ^a   Alliot, Julien ^a   Li, Mengzhou ^a   Lautens, Mark ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYST ACTIVITY; CHEMICAL BONDS; NITRILE RESINS; PALLADIUM; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ALKYL HALIDES; AROMATIC NITRILES; METAL CYANIDES;

AROMATIC COMPOUNDS;

AROMATIC COMPOUND; BROMIDE; CYANIDE; HALIDE; NITRILE; PALLADIUM;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; METALLATION; SUBSTITUTION REACTION; SYNTHESIS;

ALKYLATION; BENZENE DERIVATIVES; HYDROCARBONS, HALOGENATED; NITRILES; NORBORNANES; PALLADIUM;

EID: 37049008699     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja075599i     Document Type: Article

References (28)

1. Mariampillai, B.; Alberico, D.; Bidau, V.; Lautens, M. J. Am. Chem. Soc. 2006, 128, 14436-14437.
2. For recent work and review on palladium-catalyzed C-H functionalization, see: (a) Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7274-7276.
3. (b) Covell, D. J.; Vermeulen, N. A.; Labenz, N. A.; White, M. C. Angew. Chem., Int. Ed. 2006, 45, 8217-8220.
4. (c) Delcamp, J. H.; White, M. C. J. Am. Chem. Soc. 2006, 128, 15076-15077.
5. (d) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172-1175.
6. (e) Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496-16497.
7. (f) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238.
8. For recent work on Palladium(IV) chemistry, see: (a) Welbes, L. L.; Lyons, T. W.; Cychosz, K. A.; Sanford, M. S. J. Am. Chem. Soc. 2007, 129, 5836-5837.
9. (b) Tong, X.; Beller, M.; Tse, M. K. J. Am. Chem. Soc. 2007, 129, 4906-4907.
10. (c) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924-1935.
11. Catellani, M.; Frignani, F.; Rangoni, A. Angew. Chem., Int. Ed. 1997, 36, 119-122.
12. For recent work on synthesis and mechanistic studies, see: (a) Ferraccioli, R.; Carenzi, D.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2006, 128, 722-723.
13. (b) Catellani, M.; Motti, E.; Faccini, F.; Ferraccioli, R. Pure Appl. Chem. 2005, 77, 1243-1248.
14. (c) Rudolph, A.; Rackelmann, N.; Lautens, M. Angew. Chem., Int. Ed. 2007, 46, 1485-1488.
15. (d) Martins, A.; Alberico, D.; Lautens, M. Org. Lett. 2006, 8, 4827-4829.
16. (e) Cardenas, D. J.; Martin-Matute, B.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 5033-5040.
17. (f) Canty, A. J. In Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-i., de Meijere, A., Eds.; Wiley-Interscience: New York, 2002; pp 189-211.
18. For a review on microwave-assisted organic synthesis, see: Lidstrom, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron 2001, 57, 9225-9283.
19. (a) Schareina, T.; Zapf, A.; Beller, M. Chem. Commun. 2004, 12, 388-1389.
20. (b) Schareina, T.; Zapf, A.; Maegerlein, W.; Mueller, N.; Beller, M. Tetrahedron Lett. 2007, 48, 1087-1090.
21. (a) Zhou, J.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 12527-12530.
22. (b) Hills, I. D.; Netherton, M. R.; Fu, G. C. Angew. Chem., Int. Ed. 2003, 42, 5749-5752.
23. (c) Kirchhoff, J. H.; Dai, C.; Fu, G. C. Angew. Chem., Int. Ed. 2002, 41, 1945-1947.
24. (d) Fujii, Y.; Terao, J.; Kuniyasu, H.; Kambe, N. J. Organomet. Chem. 2007, 692, 375-381.
25. Netherton, M. R.; Fu, G. C. Org. Lett. 2001, 3, 4295-4298.
26. Faccini, F.; Motti, E.; Catellani, M. J. Am. Chem. Soc. 2004, 126, 78-79.
27. Motti, E.; Faccini, F.; Ferrari, I.; Catellani, M.; Ferraccioli, R. Org. Lett. 2006, 8, 3967-3970.
28. Previously reported by Beugelmans, R.; Bois-Choussy, M.; Chastanet, J.; Le Gleuher, M.; Zhu, J. Heterocycles 1993, 36, 2723-2732.