Ruthenium-catalyzed coupling reactions of alkynes and alkenes

Synlett

Volumn , Issue 3, 1999, Pages 281-287

  Yi, Chae S ^a   Liu, Nianhong ^a  

^a Marquette University   (United States)

Author keywords

Alkenes; Alkynes; Metallacyclopentadiene; Ruthenium acetylide

Indexed keywords

ACETYLENE; ACRYLIC ACID DERIVATIVE; ALKENE DERIVATIVE; ALKYNE DERIVATIVE; RUTHENACYCLOPENTADIENE COMPLEX; RUTHENIUM; RUTHENIUM ACETYLIDE COMPLEX; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; DIMERIZATION; REACTION ANALYSIS;

EID: 0344923768     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2593     Document Type: Article

References (71)

1. (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd Ed.; John Wiley & Sons: New York, 1992.
2. (b) Bönnemann, H; Brijoux, W. In Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B.; Herrmann, W. A. Eds.; VCH: New York, 1996, Vol. 2.
3. (c) Melikyan, G. G.; Nicholas, K. M. In Modem Acetylene Chemistry, Stang, P. J.; Diederich, F. Eds.; VCH: New York, 1995.
4. (d) Schore, N. E. In Comprehensive Organic Synthesis, Trost, B. M. Ed.; Pergamon Press: New York, 1990, Vol. 5.
5. (a) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539.
6. (b) Grotjahn, D. B. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Pergamon Press: New York, 1994, Vol. 12.
7. For recent examples on the metal-mediated intermolecular alkyne coupling reactions, see: (a) Takeda, A.; Ohno, A.; Kadota, I.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 4547.
8. (b) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem.Soc. 1997, 119, 11313.
9. (c) Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086.
10. (d) O'Connor, J. M.; Hiibner, K.; Merwin, R.; Gantzel, P. K.; Fong, B. S.; Adams, M.; Rheingold, A. L. J. Am. Chem. Soc. 1997, 119, 3631.
11. (e) van Belzen, R.; Hoffmann, H.; Elsevier, C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
12. (a) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259 and references cited therein.
13. (b) Trost, B. M.; Müller, T. J. J. J. Am. Chem. Soc. 1994, 116, 4985.
14. (c) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
15. (d) Trost, B. M.; Sorum, M. T.; Chan, C.; Harms, A. E.; Rühter, G. J. Am. Chem. Soc. 1997, 119, 698.
16. (e) Trost, B. M.; Krause, L.; Portnoy, M. J. Am. Chem. Soc. 1997, 119, 11319.
17. (a) Kim, S.-H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 116, 10801.
18. (b) Kinoshita, A.; Sakakaibara, N.; Mori, M. J. Am. Chem. Soc. 1997, 119, 12388.
19. (c) Stragies, R.; Schuser, M. Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2518.
20. Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131.
21. (a) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968.
22. (a) Bianchini, C.; Casares, J. A.; Peruzzini, M.; Romerosa, A.; Zanobini, F. J. Am. Chem. Soc. 1996, 118, 4585.
23. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272.
24. Yi. C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M.; Guzei, I. A. Organometallics 1997, 16, 3729.
25. (a) Behr, A. Carbon Dioxide Activation by Metal Complexes, VCH: New York, 1988.
26. (b) Leitner, W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2207.
27. Yi, C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 1997, 16, 3910.
28. For similar ruthenium-butadienyl complexes, see: (a) Bruce, M. I.; Rodgers, J. R.; Snow, M. R.; Swincer, A. G. J. Chem. Soc., Chem. Commun. 1981, 271.
29. (b) Bruce, M. I.; Hambley, T. W.; Snow, M. R.; Swincer, A. G. Organometallics 1985, 4, 501.
30. (c) Bruce, M. I.; Duffy, D. N.; Liddell, M. J.; Tiekink, E. R. T.; Nicholson, B. K. Organometallics 1992, 11, 1527.
31. Yi, C. S.; Liu, N. Organometallics 1998, 17, 3158.
32. For examples of metal-enynyl complexes on alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508.
33. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272.
34. (c) Schafer, M.; Maher, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315.
35. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604.
36. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
37. For recent examples on the β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references cited therein,
38. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634.
39. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289.
40. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322.
41. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466.
42. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394.
43. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911.
44. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
45. Shirakawa, E.; Yoshid, H.; Kurahashi, T.; Nakao, Y.; Hiyama, T. J. Am. Chem. Soc. 1998, 120, 2975.
46. (a) Wakatsuki, Y.; Aoki, K.; Yamazaki, H. J. Am. Chem. Soc. 1974, 96, 5284.
47. (b) Wakatsuki, Y.; Aoki, K.; Yamazaki, H. J. Am. Chem. Soc. 1979, 101, 1123.
48. (c) Mitsudo, T.; Zhang, S.; Nagao, M.; Watanabe, Y. J. Chem. Soc., Chem. Commun. 1991, 598.
49. (d) Trost, B. M.; Indolese, A. F.; Müller, T. J. J.; Treptow, B. J. Am. Chem. Soc. 1995, 117, 615.
50. (e) Bianchini, C.; Caulton, K. G.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Vizza, F. Organometallics 1995, 14, 933.
51. Yi, C. S.; Torres-Lubian, J. R.; Liu, N.; Rheingold, A. L.; Guzei, I. A. Organometallics 1998, 17, 1257.
52. For discussion and examples on the metallacyclopentatriene complexes, see: (a) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712.
53. (b) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609.
54. (c) Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218.
55. (d) Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235.
56. For the similar ruthenacyclopentadiene complexes: (a) Albers, M. O.; deWaal, D. J. A.; Liles, D. C.; Robinson, D. J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986, 1680.
57. (b) Campion, B. K.; Heyn, R. H.; Tilley, T. D. Organometallics 1990, 9, 1106.
58. (c) Braun, T.; Laubender, H.; Aevert, D.; Werner, H. Chem. Ber. 1997, 130, 559.
59. 4-arene species and their implication in alkyne cyclotrimerization reactions, see: (a) Bianchini, C.; Caulton, K. G.; Chardon, C.; Doublet, M.-L.; Eisenstein, O.; Jackson, S. A.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Streib, W. E.; Vacca, A.; Vizza, F. Organometallics 1994, 13, 2010.
60. (b) Bianchini, C.; Caulton, K. G.; Foiling, K.; Meli, A.; Peruzzini, M.; Polo, A.; Vizza, F. J. Am. Chem. Soc. 1992, 114, 7290.
61. (c) Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. J. Am. Chem. Soc. 1991, 113, 5127.
62. (d) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 109, 6525.
63. (a) Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, University Science Books: Mill Valley, CA, 1987.
64. (b) Klein, R.; Schmid, R. In Applied Homogeneous Catalysis with Organometallic Compounds, Cornils, B.; Herrmann, W. A. Eds.; VCH: New York, 1996, Vol. 2.
65. (c) Koga, N.; Morokuma, K. In Theoretical Aspects of Homogeneous Catalysis, van Leeuwen, P. W. N. M.; Morokuma, K.; van Lenthe, J. H. Eds.; Kluwer Academic Publishers: Boston, 1995.
66. Yi, C. S.; Liu, N. J. Organomet. Chem. 1998, 553, 157.
67. (a) Grenouillet, P.; Neibecker, D.; Tkatchenko, I. Organometallics 1989, 13, 1130.
68. (b) McKinny, R. J.; Cotton, M. C. Organometallics 1986, 5, 1080.
69. (c) Kovalev, I. P.; Kolmogorov, Y. N.; Ignatenko, A. V.; Vinogradov, M. G.; Nikishin, G. I. Izv. Akad. Nauk SSSR, Ser. Khim. 1989, 1098.
70. (d) Suzuki, H.; Lee, D. H.; Oshima, N.; Moro-oka, Y. Organometallics 1987, 6, 1569.
71. (e) Loren, S. D.; Campion, B. K.; Heyn, R. H.; Tilley, T. D.; Bursten, B. E.; Luth, K. W. J. Am. Chem. Soc. 1989, 111, 4712.