Ruthenium-catalyzed addition of aromatic esters at the ortho C-H bonds to olefins

Chemistry Letters

Volumn , Issue 2, 1996, Pages 109-110

  Sonoda, Motohiro ^a   Kakiuchi, Fumitoshi ^a   Kamatani, Asayuki ^a   Chatani, Naoto ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030532360     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.109     Document Type: Article

References (19)

1. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Nature (London), 366, 529 (1993).
2. S. Murai, F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, and N. Chatani, Pure Appl. Chem., 66, 1527 (1994).
3. S. Murai, J. Synth. Org. Chem., Jpn., 52, 992 (1994).
4. F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
5. F. Kakiuchi, Y. Tanaka, T. Sato, N. Chatani, and S. Murai, Chem. Lett., 1995, 679.
6. F. Kakiuchi, Y. Yamauchi, N. Chatani, and S. Murai, Chem. Lett., in press (accompanying paper).
7. F. Kakiuchi, Y. Yamamoto, N. Chatani, and S. Murai, Chem. Lett., 1995, 681.
8. a) Y.-G. Lim, Y. H. Kim, and J.-B. Kang, J. Chem. Soc., Chem. Commun., 1994, 2267;
9. b) H. Guo and W. P. Weber, Polymer Bull., 32, 525 (1994);
10. c) H. Guo, M. A. Tapsak, and W. P. Weber, Polymer Bull., 33, 417 (1994);
11. d) B. M. Trost, K. Imi, and I. W. Davies, J. Am. Chem. Soc., 117, 5371 (1995);
12. e) N. A. Williams, Y. Uchimaru, and M. Tanaka, J. Chem. Soc., Chem. Commun., 1995, 1129.
13. The yields were determined by GC unless otherwise noted.
14. 3) was vigorously refluxed (oil bath temperature, 135 °C) with stirring. After heating for 24 hours, the mixture was allowed to cool to room temperature, and toluene and 2 were removed by rotary evaporation. The product was isolated by bulb-to-bulb distillation (170 °C/2 mmHg) in 97% yield. The GC yield was determined by a separate run under the same reaction conditions except for addition of hexadecane as an internal standard for GC.
15. M. Sonoda, F. Kakiuchi, N. Chatani, and S. Murai, J. Organomet. Chem., in press.
16. The σ-electron withdrawing group can accelerate either the C-H cleavage step or the reductive elimination step.
17. The Rh-catalyzed dimerization of methyl acrylate seems to proceed via a hydrometallation-carbometallation-dehydrometallation mechanism, see: a) M. Brookhart and S. Sabo-Etienne, J. Am. Chem. Soc., 113, 2777 (1991);
18. b) M. Brookhart and E. Hauptman, J. Am. Chem. Soc., 114, 4437 (1992);
19. c) E. Hauptman, S. Sabo-Etienne, P. S. White, M. Brookhart, J. M. Garner, P. J. Pagan, and J. C. Calabrese, J. Am. Chem. Soc., 116, 8038 (1994).