Rhenium-catalyzed insertion of nonpolar and polar unsaturated molecules into an olefinic C-H bond

Organic Letters

Volumn 11, Issue 12, 2009, Pages 2711-2714

  Kuninobu, Yoichiro ^a   Fujii, Yasuo ^a   Matsuki, Takashi ^a   Nishina, Yuta ^a   Takai, Kazuhiko ^a  

^a OKAYAMA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 67149131858     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900962v     Document Type: Article

References (26)

1. Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009-3066.
2. Jia, C.; Piao, D.; Oyamada, J.; Lu, W.; Kitamura, T.; Fujiwara, Y. Science 2000, 287, 1992-1995.
3. (a) Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043
4. (b) Trnka, T. M.; Grubbs, R. H. Ace. Chem. Res. 2001, 34, 18-29.
5. (a) Kakiuchi, F.; Tanaka, Y.; Sato, T.; Chatani, N.; Murai, S. Chem. Lett. 1995, 679-680
6. (b) Trost, B. M.; Imi, K.; Davies, I. W. J. Am. Chem. Soc. 1995, 117, 5371-5372
7. (c) Kakiuchi, F.; Sato, T.; Igi, K.; Chatani, N.; Murai, S. Chem. Lett. 2001, 386-387
8. (d) Lim, Y.-G.; Kang, J.-B.; Lee, K.; Kim, Y. H. Heteroatom Chem. 2002, 13, 346-350.
9. Fujii, N.; Kakiuchi, R.; Yamada, A.; Chatani, N.; Murai, S. Chem. Lett. 1997, 425-426.
10. Chatani, N.; Ishii, Y.; Ie, Y.; Kakiuchi, F.; Murai, S. J. Org. Chem. 1998, 63, 5129-5136.
11. There have been several reports on ruthenium- and rhodium-catalyzed transformations via C-H bond activation, (a) Kakiuchi, F.; Murai, S. Top. Organomet. Chem. 1999, 3, 47-79
12. (b) Guari, Y.; Sabo-Etienne, S.; Chaudret, B. Em. J. Inorg. Chem. 1999, 1047-1055
13. (c) Dyker, G. Angew, Chem., Int. Ed. 1999, 38, 1698-1712.
14. We have reported on rhenium- and manganese-catalyzed transformations via C-Ft bond activation, (a) Kuninobu, Y.; Kawata, A.; Takai, K. J. Am. Chem. Soc. 2005, 127, 13498-13499
15. (b) Kuninobu, Y.; Nishina, Y.; Shouho, M.; Takai, K. Angew. Chem., Int. Ed. 2006, 45, 2766-2768
16. (c) Kuninobu, Y.; Inoue, Y.; Takai, K. Chem. Leu. 2006, 35, 1376-1377
17. (d) Kuninobu, Y.; Kikuchi, K.; Takai, K. Chem, Lett. 2008, 37, 740-741
18. (e) Kuninobu, Y.; Nishina, Y.; Matsuki, T.; Takai, K. J. Am. Chem. Soc. 2008, 130, 14062-14063.
19. 3, did not promote the reaction.
20. Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2006, 128, 5604-5605.
21. Silyl ether 7a was decomposed slightly during the isolation process. Therefore, the isolated vield was decreased compared with IH NMR yield.
22. For the insertion of internal alkynes into an olefinic C-H bond, see: (a) Yotphan, S.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 2452-2453
23. (b) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645-3651,
24. For rhenium-catalyzed insertion of aldehydes into an aromatic C-H bond, see: (a) Kuninobu, Y.; Nishina, Y.; Nakagawa, C.; Takai, K. J. Am. Chem. Soc. 2006, 128. 12376-12377
25. (b) Kuninobu, Y.; Nishina, Y.; Takai, K. Tetrahedron 2007, 63, 8463-8468.
26. For manganese-catalyzed insertion of aldehydes into an aromatic C-H bond, see: (a) Kuninobu, Y.; Nishina, Y.; Takeuchi, T.; Takai, K. Angew. Chem., Int. Ed. 2007, 46, 6518-6520.