Selective dimerization of arylalkynes to (E)-1,4-diaryl enynes catalyzed by the [Ru(p-cymene)Cl2]2/acetic acid system under phosphine-free conditions

Journal of Organic Chemistry

Volumn 72, Issue 12, 2007, Pages 4558-4561

  Bassetti, Mauro ^a   Pasquini, Chiara ^a   Raneri, Antonino ^a   Rosato, Deborah ^a  

^a SAPIENZA UNIVERSITY OF ROME   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

APROTIC COSOLVENTS; AROMATIC ALKYNES; PHOSPHINE;

ACETIC ACID; AROMATIC COMPOUNDS; DIMERIZATION; PHOSPHORUS COMPOUNDS; STEREOSELECTIVITY;

HYDROCARBONS;

1,4 DIARYLBUT 1 ENE 3 YNE DERIVATIVE; ACETIC ACID; ALKYNE DERIVATIVE; DI MU CHLOROBIS[(4 CYMENE)CHLORORUTHENIUM]; PHOSPHINE; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIMERIZATION; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 34250163523     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0702692     Document Type: Article

References (55)

1. (a) Handbook of C-H Transformations; Dyker, G., Ed.; Wiley-VCH: Weinheim, 2005; Vol. 1, Chapter II, p 62.
2. (b) Wakatsuki, Y. J. Organomet. Chem. 2004, 689, 4092-4109.
3. (c) Trost, B. M.; Toste, F. D.; Pinkerton, A. B. Chem. Rev. 2001, 101, 2067-2096.
4. (d) Bruneau, C.; Dixneuf, P. H. Acc. Chem. Res. 1999, 32, 311-323.
5. Nicolau, K. C.; Dai, W. M.; Tsay, S. C.; Estevez, V. A.; Wrasidlo, W. Science 1992, 256, 1172-1178.
6. (a) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem. Int. Ed. 2000, 39, 2632-2657 and references therein.
7. (b) Pahadi, N. K.; Camacho, D. H.; Nakamura, I.; Yamamoto, Y. J. Org. Chem. 2006, 71, 1152-1155.
8. (c) Liu, Y.; Nishiura, M.; Wang, Y.; Hou, Z. J. Am. Chem. Soc. 2006, 128, 5592-5593.
9. (a) Korolev, A. V.; Guzei, I. A.; Jordan, R. F. J. Am. Chem. Soc. 1999, 121, 11605-11606.
10. (b) Dash, A. K.; Eisen, M. S. Org. Lett. 2000, 2, 737-740.
11. (a) Straub, T.; Haskel, A.; Eisen, M. J. Am. Chem. Soc. 1995, 117, 6364-6365.
12. (b) Nishiura, M.; Hou, Z.; Wakatsuki, Y.; Yamaki. T.; Miyamoto, T. J. Am. Chem. Soc. 2003, 125, 1184-1185.
13. (c) Nishiura, M.; Hou, Z. J. Mol. Catal. A 2004, 213, 101-106.
14. (a) Trost, B. M.; Chan, C.; Ruhter, G. J. Am. Chem. Soc. 1987, 109, 3486-3487.
15. (b) Jun, C.-H.; Lu, Z.; Crabtree, R. H. Tetrahedron Lett. 1992, 33, 7119-7120.
16. (c) Balcioǧlu, N.; Uraz, İ.; Bozkurt, C.; Sevin, F. Polyhedron 1997, 16, 327-334.
17. (d) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508-4510.
18. (e) Field, L. D.; Ward, A. J.; Turner, P. Aust. J. Chem. 1999, 52, 1085-1092.
19. (f) Ogoshi, S.; Ueta, M.; Oka, M.; Kurosawa, H. Chem. Commun. 2004, 2732-2733.
20. (a) Rubina, M.; Gevorgyan, V. J. Am. Chem. Soc. 2001, 123, 11107-11108.
21. (b) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591-593.
22. (a) Ohshita, J.; Furumori, K.; Matsuguchi, A.; Ishikawa, M. J. Org. Chem. 1990, 55, 3277-3280.
23. (b) Kovalev, I. P.; Yevdakov, K. V.; Strelenko, Y. A.; Vinogradov, M. G.; Nikishin, G. I. J. Organomet. Chem. 1990, 386, 139-146.
24. (c) Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782-786.
25. (a) Wendt, J.; Klinger, U.; Singer, H. Inorg. Chim. Acta 1991, 183, 133-143.
26. (b) Lee, C.-C.; Lin, Y.-C.; Liu, Y.-H.; Wang, Y. Organometallics 2005, 24, 136-143.
27. (c) Weng, W.; Guo, C.; Çelenligil-Çetin, R.; Foxman, B. M.; Ozerov, O. V. Chem. Commun. 2006, 197-199.
28. (a) Dahlenburg, L.; Frosin, K.-M.; Kerstan, S.; Werner, D. J. Organomet. Chem. 1991, 407, 115-124.
29. (b) Bianchini, C.; Peruzzini, M.; Zanobini, F.; Frediani, P.; Albinati, A. J. Am. Chem. Soc. 1991, 113, 5453-5454.
30. (c) Echavarren, A. M.; Lopez, J.; Santos, A.; Montoya, J. J. Organomet. Chem. 1991, 414, 393-400.
31. (d) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968-3971.
32. (e) Slugovc, C.; Mereiter, K.; Zobetz, E.; Schmid, R.; Kirchner, K. Organometallics 1996, 15, 5275-5277.
33. (f) Fryzuk, M. D.; Jonker, M. J.; Rettig, S. J. Chem. Commun. 1997, 377-378.
34. (g) Yi, C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 1997, 16, 3910-3913.
35. (h) Qü, J.-P.; Masui, D.; Ishii, Y.; Hidai, M. Chem. Lett. 1998, 1003-1004.
36. (i) Matsuzaka, H.; Ichikawa, K.; Ishii, T.; Kondo, M.; Kitagawa, S. Chem. Lett. 1998, 1175-1176.
37. (j) Bassetti, M.; Marini, S.; Tortorella, F.; Cadierno, V.; Díez, J.; Gamasa, M. P.; Gimeno, J. J. Organomet. Chem. 2000, 593-594, 292-298.
38. (k) Baratta, W.; Herrmann, W. A.; Rigo, P.; Schwarz, J. J. Organomet. Chem. 2000, 593-594, 489-493.
39. (l) Pavlik, S.; Gemel, C.; Sluogovc, C.; Mereiter, K.; Schmid, R.; Kirchner, K. J. Organomet. Chem. 2001, 617-618, 301-310.
40. (m) Katayama, H.; Nakayama, M.; Nakano, T.; Wada, C.; Akamatsu, K.; Ozawa, F. Macromolecules 2004, 37, 13-17.
41. Chen, X.; Xue, P.; Sung, H. H. Y.; Williams, I. D.; Peruzzini, M.; Bianchini, C.; Jia, G. Organometallics 2005, 24, 4330-4332.
42. Katayama, H.; Yari, H.; Tanaka, M.; Ozawa, F. Chem. Commun. 2005, 4336-4338.
43. Bianchini, C.; Frediani, P.; Masi, D.; Peruzzini, M.; Zanobini, F. Organometallics 1994, 13, 4616-4632.
44. (a) Melis, K.; De Vos, D.; Jacobs, P.; Verpoort, F. J. Organomet. Chem. 2002, 659, 159-164.
45. (b) Melis, K.; De Vos, D.; Jacobs, P.; Verpoort, F. J. Organomet. Chem. 2003, 671, 131-136.
46. Bassetti, M.; Marini, S.; Diaz, J.; Gamasa, M. P.; Gimeno, J.; Rodríguez-Álvarez, Y.; García-Granda, S. Organometallics 2002, 21, 4815-4822.
47. (a) Melis, K.; Opstal, T.; Verpoort, F. Eur. J. Org. Chem. 2002, 3779-3784.
48. (b) le Paih, J.; Monnier, F.; Dérien, S.; Dixneuf, P. H.; Clot, E.; Eisenstein, O. J. Am. Chem. Soc. 2003, 125, 11964-11975.
49. Matsuzaka, H.; Takagi, Y.; Ishii, Y.; Nishio, M.; Hidai, M. Organometallics 1995, 14, 2153-2155.
50. Herberhold, M.; Yan, H.; Milius, W.; Wrackmeyer, B. J. Organomet. Chem. 2001, 623, 149-152.
51. Bassetti, M.; Floris, B.; Illuminati, G. Organometallics 1985, 4, 617-623.
52. (a) Menashe, N.; Shvo, Y. J. Org. Chem. 1993, 58, 7434-7439.
53. (b) Alonso, F.; Beletskaya, I. P.; Yus, M. Chem. Rev. 2004, 104, 3079-3159.
54. Tocher, D. A.; Gould, R. O.; Stephenson, T. A.; Bennett, M. A.; Ennett, J. P.; Matheson, T. W.; Sawyer, L.; Shah, V. K. J. Chem. Soc. Dalton Trans. 1983, 1571-1581.
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