Benzannulation from alkyne without metallic catalysts at room temperature to 100 °C

Organic Letters

Volumn 12, Issue 2, 2010, Pages 388-390

  Jin, Tienan ^a   Yang, Fan ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 74949130206     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol902742u     Document Type: Article

References (31)

1. (a) Berthelot, M. C. R. Acad. Sci. 1866, 62, 905-909.
2. (b) Repee, W.; Schweckendiek, W. J. Justus Liebigs Ann. Chem. 1948, 560, 104-116.
3. (c) Vollhardt, K. P. C. Angew. Chem., Int. Ed. 1984, 23, 539-556.
4. For reviews, see: (a) Koüia, S.; Misra, S.; Halder, S. Tetrahedron 2008, 64, 10775-10790.
5. (b) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915.
6. (c) Dotz, K. H.; Tomuschat, P. Chem. Soc. Rev. 1999, 28, 187-198.
7. (d) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
8. (e) Trost, B. M. Science 1991, 254, 1471-1477.
9. For reviews, see: (a) Gevorgyan, V.; Yamamoto, Y. J. Orgnomet. Chem. 1999, 576, 232-247.
10. (b) Yamamoto, Y. J. Org. Chem. 2007, 72, 7817-7831.
11. Horvath, I. T.; Anastas, P. T. Chem. Rev. 2007, 107, 2169-2173.
12. (a) Merlic, C. A.; Burns, E. E.; Xu, D.; Chen, S. Y. J. Am. Chem. Soc. 1992, 114, 8722-8724.
13. (b) Merlic, C. A.; Aldrich, C. C.; AlbanezeWalker, J.; Saghatelian, A.; Mammen, J. Org. Chem. 2001, 66, 1297-1309.
14. (c) Merlic, C. A.; Xu, D.; Gladstone, B. G. J. Org. Chem. 1993, 58, 538-545.
15. (a) Herndon, J. W.; Zhang, Y.; Wang, K. J. Organomet. Chem. 2001, 634, 1-4.
16. (b) Belmont, P.; Belhadj, T. Org. Lett. 2005, 7, 1793-1795.
17. (c) Tiano, M.; Belmont, P. J. Org. Chem. 2008, 73, 4101-4109.
18. (d) Facoetti, D.; Abbiati, G.; Rossi, E. Eur. J. Org. Chem. 2009, 2872-2882.
19. (a) Sagar, P.; Fröhlich, R.; Würthwein, E.-U. Angew. Chem., Int. Ed. 2004, 43, 5694-5697.
20. (b) Lyaskovskyy, V.; Fröhlich, R.; Würthwein, E.-U. Synthesis 2007, 2135-2144.
21. (a) Tipton, K. F.; McCrodden, J. M.; Kalir, A. S.; Youdim, M. B. H. Biochem. Pharmacol. 1982, 31, 1251-1255.
22. (b) Dukat, M.; Abdel-Rahman, A. A.; Ismaiel, A. M.; Ingher, S.; Teitler, M.; Gyermek, L.; Glennon, R. A. J. Med. Chem. 1996, 39, 4017-4026.
23. (c) Kabankin, A. S.; Kurlyandskii, B. A. Phaarm. Chem. J. 2001, 35, 257-259.
24. (d) Agdeppa, E. D.; Kepe, V.; Liu, J.; Flores-Torres, S.; Satyamurthy, N.; Petrie, A.; Cole, G. M.; Small, G. W.; Huang, S.-C.; Barrio, J. R. J. Neurosci. 2001, 21, RC189 1-5.
25. (e) Kim, H. M.; Jung, C. J.; Kim, B. R.; Jung, S.-Y.; Hong, J. H.; Ko, Y.-G.; Lee, K. J.; Cho, B. R. Angew. Chem., Int. Ed. 2007, 46, 3460-3463.
26. (k) Saudan, C.; Balzani, V.; Gorka, M.; Lee, S.-K.; Maestri, M.; Vicinelli, V.; Vogtle, F. J. Am. Chem. Soc. 2003, 125, 4424-4425.
27. Gou, F.-R.; Huo, P.-F.; Bi, H.-P.; Guan, Z.-H.; Liang, Y.-M. Org. Lett. 2009, 11, 3418-3421.
28. (a) Jin, T.; Yamamoto, Y. Org. Lett. 2007, 9, 5259-5262.
29. (b) Jin, T.; Yamamoto, Y. Org. Lett. 2008, 10, 3137-3139.
30. (c) Jin, T.; Yang, F.; Liu, C.; Yamamoto, Y. Chem. Commun. 2009, 3533-3535.
31. An alternative plausible reaction mechanism for the formation of 2-aminonaphth.alenes is a 6-electrocyclization pathway as shown below. Chemical Equation Presentation