Ruthenium-catalyzed coupling of aromatic carbon-hydrogen bonds in aromatic imidates with olefins

Chemistry Letters

Volumn , Issue 1, 1999, Pages 19-20

  Kakiuchi, Fumitoshi ^a   Sato, Taisuke ^a   Yamauchi, Masakazu ^a   Chatani, Naoto ^a   Murai, Shinji ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033238893     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.19     Document Type: Article

References (21)

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4. b) F. Kakiuchi, S. Sekine, Y. Tanaka, A. Kamatani, M. Sonoda, N. Chatani, and S. Murai, Bull. Chem. Soc. Jpn., 68, 62 (1995).
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6. d) F. Kakiuchi, M. Yamauchi, N. Chatani, and S. Murai Chem. Lett. 1996, 111.
7. 12 complex is effective in the coupling reaction of aromatic imines with olefins. See, Ref. 3d.
8. For the examples of the cleavage of a C-H bond adjacent to a nitrogen atom, see: S.-I. Murahashi, T. Naota, and K. Yonemura, J. Am. Chem. Soc., 110, 8256 (1988).
9. Very recently, we reported on a new catalytic reaction involving the cleavage of a C-H bond adjacent to a nitrogen atom, see: Y. Ishii, N. Chatani, F. Kakiuchi, and S. Murai, Organometallics, 16, 3615 (1997); Y. Ishii, N. Chatani, F. Kakiuchi, and S. Murai, Tetrahedron Lett., 38, 7565 (1997).
10. Very recently, we reported on a new catalytic reaction involving the cleavage of a C-H bond adjacent to a nitrogen atom, see: Y. Ishii, N. Chatani, F. Kakiuchi, and S. Murai, Organometallics, 16, 3615 (1997); Y. Ishii, N. Chatani, F. Kakiuchi, and S. Murai, Tetrahedron Lett., 38, 7565 (1997).
11. A similar olefinic product was observed in the catalytic reaction of aromatic imines but only in low yields (Ref. 3d)
12. The Ru-catalyzed coupling of aromatic ketones with olefins did not give rise to any unsaturated by-products. See, Refs. 3a-c.
13. The introduction of a methyl group on the aromatic ring is important in suppressing the formation of the 1:2 coupling product.
14. J. Y. Corey, "Advances in Silicon Chemistry," ed by G. L. Larson, JAI Press, Greenwich, Conneticut (1991), pp. 327-387.
15. B. Marciniec and J. Guliñski, J. Organomet. Chem., 266, C19 (1984); Y. Seki, K. Takeshita, and K. Kawamoto, J. Organomet. Chem., 369, 117 (1989); Y. Wakatsuki, H. Yamazaki, M. Nakano, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1991, 703; B. Marciniec and C. Pietraszuk, J. Chem. Soc., Chem. Commun., 1995, 2003.
16. B. Marciniec and J. Guliñski, J. Organomet. Chem., 266, C19 (1984); Y. Seki, K. Takeshita, and K. Kawamoto, J. Organomet. Chem., 369, 117 (1989); Y. Wakatsuki, H. Yamazaki, M. Nakano, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1991, 703; B. Marciniec and C. Pietraszuk, J. Chem. Soc., Chem. Commun., 1995, 2003.
17. B. Marciniec and J. Guliñski, J. Organomet. Chem., 266, C19 (1984); Y. Seki, K. Takeshita, and K. Kawamoto, J. Organomet. Chem., 369, 117 (1989); Y. Wakatsuki, H. Yamazaki, M. Nakano, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1991, 703; B. Marciniec and C. Pietraszuk, J. Chem. Soc., Chem. Commun., 1995, 2003.
18. B. Marciniec and J. Guliñski, J. Organomet. Chem., 266, C19 (1984); Y. Seki, K. Takeshita, and K. Kawamoto, J. Organomet. Chem., 369, 117 (1989); Y. Wakatsuki, H. Yamazaki, M. Nakano, and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1991, 703; B. Marciniec and C. Pietraszuk, J. Chem. Soc., Chem. Commun., 1995, 2003.
19. The corresponding bis(silyl)ethylenes have been detected in ca. 20-40% yields (2 mmol-4 mmol) based the vinylsilane charged.
20. Since the reactions of 7 with vinylsilanes were carried out in vigorously refluxing toluene, ethylene that should have been generated by the disproportionation of the vinylsilanes seemed to have gone away from the reaction mixture. So, the corresponding ethylation product could have not been detected by GC analysis.
21. Carbon monoxide is assumed to arise from the ruthenium carbonyl complex.