Heterodinuclear complex Cp*Ru(Co)2Co(Co)4 (Cp* = η5-C5Me5) induced selective dimerization of terminal alkynes

Chemistry Letters

Volumn , Issue 11, 1998, Pages 1175-1176

  Matsuzaka, Hiroyuki ^a   Ichikawa, Koji ^a   Ishii, Tomohiko ^a   Kondo, Mitsuru ^a,b   Kitagawa, Susumu ^a,b  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001989131     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1998.1175     Document Type: Article

References (29)

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6. 6Ru: C, 41.47; H, 3.26%.
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10. 1H NMR analysis of the crude reaction mixture indicates the absence of free oligomers derived from the alkyne such as (F)-TolCH=CHC≡CTol.
11. 2(Fo)] for 2683 reflections with 1 > 3σ(1) (5° < 2θ < 55°, 325 parameters). The structure was solved and refined with teXsan program package.
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19. 2O. however we must await further investigation on the mechanism of its formation.
20. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
21. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
22. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
23. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
24. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
25. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
26. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
27. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
28. Selective head-to-head coupling of terminal alkynesto form trans-enynes has been reported. See: M. Ishikawa, J. Ohshita, K. Furumori, A. Matsuguchi, and M. Ishikawa, J. Org. Chem., 55, 3277 (1990); C.-H. Jun, Z. Lu, and R. H. Crabtree, Tetrahedron Lett., 1992, 33, 7119; M. A. Esteruelas, L. A. Oro, and N. Ruiz, Organometallics, 13, 1507 (1994); C. Bianchini, P. Frediani, M. Peruzzini, and F. Zanobini, Organoemetallics, 13, 4616 (1994); T. Rappert and A. Yamamuto, Organometallics, 13, 4984 (1994); C. Slugovc, K. Mereiter, E. Zobetz, R. Schmid, and K. Kirchner, Organometallics, 15, 5275 (1996); C. S. Yi and N. Liu, Organometallics, 15, 3968 (1996); M. D. Fryzuk, M. J. Jonker, and S. J. S. Rettig, J. Chem. Soc., Chem. Commun., 1997, 377; C. Gemel, G. Kickelbick, R. Schmid, and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 2113.
29. 1H NMR analysis indicates the absence of 1 in the crude reaction mixture but instead several Cp* resonances were observed around δ 2 ppm.