FeCl3-mediated reaction of 1,4-dilithio-1,3-dienes with alkynes affording benzene derivatives

Chinese Journal of Chemistry

Volumn 21, Issue 3, 2003, Pages 219-221

  Li, Guo Tao ^a   Fang, Hong Yun ^a   Li, Zhi Ping ^a   Xi, Zhen Feng ^a,b  

^a PEKING UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

1,4 Dilithio 1,3 dienes; Alkenyl iron; Alkynes; Aromatic compounds; FeCl3; Formal 4 + 2 cycloaddition; Organolithium compounds

Indexed keywords

EID: 0142229844     PISSN: 1001604X     EISSN: None     Source Type: Journal    
DOI: 10.1002/cjoc.20030210302     Document Type: Article

References (20)

1. (a) Whitmire, K. H. In Comprehensive Organometallic Chemistry II, Vol. 7, Eds.: Abel, E. D.; Stone, F. G. A.; Wilkinson, G.; Shriver, D. F.; Bruce, M. I., Pergamon, Oxford, 1995, p. 1.
2. (b) Keiber, R. C. In Comprehensive Organometallic Chemistry II, Vol. 7, Eds.: Abel, E. D.; Stone, F. G. A.; Wilkinson, G.; Shriver, D. F.; Bruce, M. I., Pergamon, Oxford, 1995, p. 101.
3. (c) Fagan, P. J. In Comprehensive Organometallic Chemistry II, Vol. 7, Eds.: Abel, E. D.; Stone, F. G. A.; Wilkinson, G.; Shriver, D. F.; Bruce, M. I., Pergamon, Oxford, 1995, p. 231.
4. (d) Akita, M. In Comprehensive Organometallic Chemistry II, Vol. 7, Eds.: Abel, E. D.; Stone, F. G. A.; Wilkinson, G.; Shriver, D. F.; Bruce, M. I., Pergamon, Oxford, 1995, p. 259.
5. (e) Dotz, K. H.; Popall, M. Tetrahedron 1985, 41, 5797.
6. Xi, Z. F.; Song, Q. L. J. Org. Chem. 2000, 65, 9157.
7. (a) Xi, Z. F.; Song, Q. L.; Chen, J. L.; Guan, H. R.; Li, P. X. Angew. Chem., Int. Ed. 2001, 40, 1913.
8. (b) Chen, J. L.; Song, Q. L.; Li, P. X.; Guan, H. R.; Jin, X. L. Org. Lett. 2002, 4, 2269.
9. Xi, Z. F.; Li, P. X.; Song, Q. L.; Chen, J. L. Chin. J. Org. Chem. 2001, 21, 824 (in Chinese).
10. Chen, J. L.; Song, Q. L.; Xi, Z. F. Tetrahedron Lett. 2002, 43, 3533.
11. Song, Q. L.; Chen, J. L.; Jin, X. L.; Xi, Z. F. J. Am. Chem. Soc. 2001, 123, 10419.
12. Chen, J. L.; Song, Q. L.; Wang, C. Y.; Xi, Z. F. J. Am. Chem. Soc. 2002, 124, 6238.
13. Transition metal mediated preparation of aromatic compounds involving alkynes, see: (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
14. (b) Schore, N. E. Chem. Rev. 1988, 88, 1081.
15. (c) Lautens, M.; Mute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
16. (d) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
17. (e) Takahashi, T.; Xi, Z. F.; Yamazaki, A.; Liu, Y. H.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1998, 120, 1672.
18. (f) Takahashi, T.; Tsai, F.; Li, Y. Z.; Nakajima, K.; Kotora, M. J. Am. Chem. Soc. 1999, 121, 11093.
19. (g) Xi, Z. F; Takahashi, T. Acta Chim. Sinica 2000, 58, 1177 (in Chinese).
20. 42 330.3286, found 330.3281.