Ruthenium-promoted Z-selective head-to-head dimerization of terminal alkynes in organic and aqueous media

Organometallics

Volumn 24, Issue 18, 2005, Pages 4330-4332

  Chen, Xingguo ^a   Xue, Peng ^a   Sung, Herman H Y ^a   Williams, Ian D ^a   Peruzzini, Maurizio ^b   Bianchini, Claudio ^b   Jia, Guochen ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

^b ICCOM CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSIS; ORGANIC CHEMICALS; RUTHENIUM; STEREOCHEMISTRY;

ALIPHATIC ALKYNES; AROMATIC ALKYNES; FUNCTIONAL GROUPS; STEREOSELECTIVITY;

DIMERIZATION;

EID: 24944453067     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om050355x     Document Type: Article

References (33)

1. Reviews: (a) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311.
2. (b) Ritleng, V.; Sirlin, C.; Pfeffer, M. Chem. Rev. 2002, 102, 1731.
3. (c) Katayama, H.; Ozawa, F. Coord. Chem. Rev. 2004, 248, 1703.
4. (d) Yi, C. S.; Liu, N. Synlett 1999, 281.
5. Z-Selective head-to-head dimerization of aromatic alkynes: (a) Nishiura, M.; Hou, Z.; Wakatsuki, Y.; Yamaki, T.; Miyamoto, T. J. Am. Chem. Soc. 2003, 125, 1184.
6. (b) Tazelaar, C. G. J.; Bambirra, S.; van Leusen, D.; Meetsma, A.; Hessen, B.; Teuben, J. H. Organometallics 2004, 23, 936.
7. (c) Katayama, H.; Nakayama, M.; Nakano, T.; Wada, C.; Akamastsu, K.; Ozawa, F. Macromolecules 2004, 37, 13.
8. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
9. (e) Echevarren, A. M.; Lopez, J.; Santos, A.; Montoya, J. J. Organomet. Chem. 1991, 414, 393.
10. Z-Selective head-to-head dimerization of aliphatic alkynes: (a) Qu, J. P.; Masui, D.; Ishii, Y.; Hidai, M. Chem. Lett. 1998, 1003.
11. (b) Jun, C.-H.; Lu, Z.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119.
12. (c) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275.
13. (d) Pavlik, S.; Gemel, C.; Slugovc, C.; Mereiter, K.; Schmid, R.; Kichner, K. J. Organomet. Chem. 2001, 617, 301.
14. (a) Bianchini, C.; Peruzzini, M.; Zanobini, F.; Frediani, P.; Albinati, A. J. Am. Chem. Soc. 1991, 113, 5453.
15. (b) Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616.
16. (c) Barbaro, C.; Bianchini, C.; Peruzzini, M.; Polo, A.; Zanobini, F.; Frediani, P. Inorg. Chim. Acta 1994, 220, 5.
17. (d) Bianchini, C.; Bohanna, C.; Esteruelas, M. A.; Frediani, P.; Meli, A.; Oro, L. A.; Peruzzini, M. Organometallics 1992, 11, 3837.
18. Dahlenburg, L.; Frosin, K.-M.; Kerstan, S.; Werner, D. J. Organomet. Chem. 1991, 407, 115.
19. Additional examples of recent work: (a) Schafer, M.; Wolf, J.; Werner, H. Organometallics 2004, 23, 5173.
20. (b) Horacek, M.; Stepnicka, P.; Kubista, J.; Gyepes, R.; Mach, K. Organometallics 2004, 23, 3388.
21. (c) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591.
22. (d) Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 11107.
23. (e) Lee, C. C.; Lin, Y. C.; Liu, Y. H.; Wang, Y. Organometallics 2005, 24, 136.
24. See the Supporting Information for experimental and spectroscopic details of the new compounds.
25. Trost, B. M.; Rudd, M. T. J. Am. Chem. Soc. 2001, 123, 8862.
26. (a) Doucet, H.; Martin-Vaca, B.; Bruneau, C.; Dixneuf, P. H. J. Org. Chem. 1995, 60, 7247.
27. (b) Le Paih, J.; Monnier, F.; Derien, S.; Dixneuf, P. H.; Clot, E.; Eisenstein, O. J. Am. Chem. Soc. 2003, 125, 11964.
28. Bianchini, C.; Meli, A.; Peruzzini, M.; Zanobini, F.; Bruneau, C.; Dixneuf, P. H. Organometallics 1990, 9, 1155.
29. Joo, F. Aqueous Organometallic Catalysis; Kluwer: Dordrecht, The Netherlands, 2001.
30. Rh-catalyzed dimerization reactions of arylalkynes to give mixtures of enynes in toluene/pyridine/water are known: Baidossi, W.; Goren, N.; Blum, J.; Schumann, H.; Hemling, H. J. Mol. Catal. 1993, 85, 153.
31. Tokunaga, M.; Suzuki, T.; Koga, N.; Fukushima, T.; Horiuchi, A.; Wakatsuki, Y. J. Am. Chem. Soc. 2001, 123, 11917.
32. (b) Grotjahn, D. B.; Lev, D. A. J. Am. Chem. Soc. 2004, 126, 12232.
33. Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585.