Low-valent niobium-mediated synthesis of indenes: Intramolecular coupling reaction of CF3 group with alkene C-H bond

Chemistry Letters

Volumn 36, Issue 1, 2007, Pages 24-25

  Fuchibe, Kohei ^a   Mitomi, Ken ^a   Akiyama, Takahiko ^a  

^a GAKUSHUIN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 34247229206     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2007.24     Document Type: Article

References (37)

1. a) A. Korte, J. Legros, C. Bolm, Synlett 2004, 2397.
2. b) D. C. Harrowven, N. A. Newman, C. A. Knight, Tetrahedron Lett, 1998, 39, 6757.
3. c) Y. Ishiguro, K. Okamoto, F. Ojima, Y. Sododa, Chem. Lett. 1993, 1139.
4. d) Y. Wang, S.-Y. Mo, S.-J. Wang, S. Li, Y.-C. Yang, J.-G. Shi, Org. Lett. 2005, 7, 1675.
5. a) R. Leino, P. Lehmus, A. Lehtonen, Eur. J. Inorg. Chem. 2004, 3201.
6. b) V. Cadiemo, J. Díez, M. P. Gamasa, J. Gimeno, E. Lastra, Coord. Chem. Rev. 1999, 193-195, 147.
7. c) D. Zargarian, Coord. Chem. Rev. 2002, 233-234, 157.
8. J. Yang, M. V. Lakshmikantham, M. P. Cava, J. Org. Chem. 2000, 65, 6739.
9. J. Barbera, O. A. Rakitin, M. B. Ros, T. Torroba, Angew. Chem., Ind. Ed. 1998, 37, 296.
10. a) M. K. Seery, S. M. Draper, J. M. Kelly, T. McCabe, T. B. H. McMurry, Synthesis 2005, 470.
11. b) Z. Xi, R. Guo, S. Mito, H. Yan, K.-i. Kanno, K. Nakajima, T. Takahashi, J. Org. Chem. 2003, 68, 1252.
12. c) P. G. Karmarkar, V. R. Chinchore, M. S. Wadia, Synthesis 1981, 228.
13. d) K. R. Romines, K. D. Lovasz, S. A. Mizsak, J. K. Morris, E. P. Seest, F. Han, J. Tulinsky, T. M. Judge, R. B. Gammill, J. Org. Chem. 1999, 64, 1733.
14. a) R. L. Halterman, C. Zhu, Tetrahedron Lett. 1999, 40, 7445.
15. b) V. G. Nenajdenko, D. I. Denisenko, E. S. Balenkova, Russ. Chem. Bull. 2002, 51, 2090.
16. a) L. G. Quan, V. Gevorgyan, Y. Yamamoto, J. Am. Chem. Soc. 1999, 121, 3545.
17. b) K.-J. Chang, D. K. Rayabarapu, C.-H. Cheng, J. Org. Chem. 2004, 69, 4781.
18. c) A. A. Pletnev, Q. Tian, R. C. Larock, J. Org. Chem. 2002, 67, 9276.
19. d) Y. Kuninobu, A. Kawata, K. Takai, J. Am. Chem. Soc. 2005, 127, 13498.
20. See also: a) H. Yamabe, A. Mizuno, H. Kusama, N. Iwasawa, J. Am. Chem. Soc. 2005, 127, 3248.
21. b) R. Shintani, K. Okamoto, T. Hayashi, J. Am. Chem. Soc. 2005, 127, 2872.
22. c) M. F. Semmelhack, S. Ho, D. Cohen, M. Steigerwald, M. C. Lee, G. Lee, A. M. Gilbert, W. D. Wulff, R. G. Ball, J. Am. Chem. Soc. 1994, 116, 7108.
23. d) T. Fukuyama, N. Chatani, F. Kakiuchi, S. Murai, J. Org. Chem. 1997, 62, 5647.
24. e) T. Jobashi, K. Maeyama, K. Noguchi, Y. Yoshida, N. Yonezawa, Bull. Chem. Soc. Jpn. 2006, 79, 627.
25. f) W. A. L. van Otterlo, E. M. Coyanis, J.-L. Panayides, C. B. de Koning, M. A. Fernandes, Synlett 2005, 501.
26. a) K. Fuchibe, T. Akiyama, J. Am. Chem. Soc. 2006, 128, 1434. See also:
27. b) K. Fuchibe, T. Akiyama, Synlett 2004, 1282.
28. 3 group: a) V. J. Scott, R. Çelenligil-Çetin, O. V. Ozerov, J. Am. Chem. Soc. 2005, 127, 2852.
29. b) H. Amii, Y. Hatamoto, M. Seo, K. Uneyama, J. Org. Chem. 2001, 66, 7216.
30. c) C. Saboureau, M. Troupel, S. Sibille, J. Périchon, J. Chem. Soc., Chem. Commun. 1989, 1138.
31. d) P. Gavel, M.-P. Léger-Lambert, C. Biran, F. Serein-Spirau, M. Bordeau, N. Roques, H. Marzouk, Synthesis 1999, 829.
32. General review on activation of inactive bonds: e) Activation of Unreactive Bonds and Organic Synthesis, ed. by S. Murai, Topics in Organometallic Chemistry, Springer, Berlin, 1999, Vol. 3.
33. Other reports on C-C bond formation via alkene C-H activation: a) M. D. K. Boele, G. P. F. van Strijdonck, A. H. M. de Vries, P. C. J. Kamer, J. G. de Vries, P. W. N. M. van Leeuwen, J. Am. Chem. Soc. 2002, 124, 1586.
34. b) Y.-G. Lim, J.-B. Kang, Y. H. Kim, Chem. Commun. 1996, 585. For general review, see reference 10e.
35. 1-Fluoro-2-phenylindene was not detected at all.
36. This selectivity is of great interest, but the reason is not clear at this moment.
37. For instance: I. E. Nifant'ev, A. A. Sitnikov, N. V. Andriukhova, I. P. Laishevtsev, Y. N. Luzikov, Tetrahedron Lett. 2002, 43, 3213.