Synthesis of fused polycyclic aromatics by palladium-catalyzed annulation of arynes using 2-halobiaryls

Journal of the American Chemical Society

Volumn 127, Issue 45, 2005, Pages 15716-15717

  Liu, Zhijian ^a   Zhang, Xiaoxia ^a   Larock, Richard C ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BIPHENYL DERIVATIVE; HALIDE; METAL; PALLADIUM; POLYCYCLIC AROMATIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ANNULATION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 27844442610     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055781o     Document Type: Article

References (21)

1. (a) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. T. Chem. Rev. 1996, 96, 935.
2. (b) Rubin, M.; Sromek, A. W.; Gevorgyan, V. Synlett 2003, 2265.
3. (a) Larock, R. C. Pure Appl. Chem. 1999, 71, 1435.
4. (b) Larock, R. C. In Topics in Organometallic Chemistry; Springer: Berlin, Germany, 2005; p 147.
5. (a) Peña, D.; Escudero, S.; Pérez, D.; Guitián, E.; Castedo, L. Angew. Chem., Int. Ed. 1998, 37, 2659.
6. (b) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. Org. Lett. 1999, 1, 1555.
7. (c) Peña, D.; Cobas, A.; Pérez, D.; Guitián, E.; Castedo, L. Org. Lett. 2000, 2, 1629.
8. (a) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Am. Chem. Soc. 1999, 121, 5827.
9. (b) Peña, D.; Pérez, D.; Guitián, E.; Castedo, L. J. Org. Chem. 2000, 65, 6944.
10. (c) Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 7280.
11. (d) Radhakrishnan, K. V.; Yoshikawa, E.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 7533.
12. Yoshikawa, E.; Yamamoto, Y. Angew. Chem., Int. Ed. 2000, 39, 173.
13. Yoshikawa, E.; Radhakrishnan, K. V.; Yamamoto, Y. Tetrahedron Lett. 2000, 41, 729.
14. Zhansi, X.; Larock, R. C. Org. Lett. 2005, 7, 3973.
15. Watson, M. D.; Fethtenkötter, A.; Müllen, K. Chem. Rev. 2001, 101, 1267.
16. Larock, R. C.; Tian, Q. J. Org. Chem. 1998, 63, 2002.
17. For the Pd-catalyzed formation of naphthalenes from an aryl halide and two alkynes, see: (a) Kawasaki, S.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 6836.
18. (b) Wu, G.; Rheingold, A. L.; Geib, S. L.; Heck, R. F. Organometallics 1987, 6, 1941.
19. (a) Matsubara, T. Organametallics 2003, 22, 4297.
20. (b) Yoshida, H.; Tanino, K.; Ohshita, J.; Kunai, A. Angew. Chem., Int. Ed. 2004, 43, 5052.
21. (c) Retbøll, M.; Edwards, A. J.; Rae, A. D.; Willis, A. C.; Bennett, M. A.; Wenger, E. J. Am. Chem. Soc. 2002, 124, 8348.