Selective linear coupling reaction of acetylene and acrylonitrile catalyzed by the well-defined metallacyclopentadiene complex C5Me5(PPh3)(Cl)RuCH=CHCH=CH

Organometallics

Volumn 17, Issue 7, 1998, Pages 1257-1259

  Yi, Chae S ^a   Torres Lubian, J Roman ^a   Liu, Nianhong ^a   Rheingold, Arnold L ^b   Guzei, Ilia A ^b  

^a Marquette University   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001581970     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9800647     Document Type: Article

References (42)

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10. 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. (b) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313. (c) Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086. (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. (e) van Belzen, R.; Hoffmann, H.; Elsevier: C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
11. 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. (b) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313. (c) Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086. (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. (e) van Belzen, R.; Hoffmann, H.; Elsevier: C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
12. 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. (b) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313. (c) Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086. (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. (e) van Belzen, R.; Hoffmann, H.; Elsevier: C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
13. 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. (b) Gevorgyan, V.; Takeda, A.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 11313. (c) Johnson, E. S.; Balaich, G. J.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 11086. (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. (e) van Belzen, R.; Hoffmann, H.; Elsevier: C. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1743.
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22. See the Supporting Information for the characterization data of complexes 1, 3, 4, and 6.
23. 3. For a recent example, see: Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887 and references therein.
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25. 3, R(F) = 3.63% for 3354 observed independent reflections (2 ≤ 2θ < 22.5°).
26. For discussion and examples of the metallacyclopentatriene complexes, see: (a) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712. (b) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609. (c) Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218. (d) Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235.
27. For discussion and examples of the metallacyclopentatriene complexes, see: (a) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712. (b) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609. (c) Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218. (d) Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235.
28. For discussion and examples of the metallacyclopentatriene complexes, see: (a) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712. (b) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609. (c) Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218. (d) Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235.
29. For discussion and examples of the metallacyclopentatriene complexes, see: (a) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 2712. (b) Pu, L.; Hasegawa, T.; Parkin, S.; Taube, H. J. Am. Chem. Soc. 1992, 114, 7609. (c) Hirpo, W.; Curtis, M. D. J. Am. Chem. Soc. 1988, 110, 5218. (d) Kerschner, J. L.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1988, 110, 8235.
30. (a) Campion, B. K.; Heyn, R. H.; Tilley, T. D. Organometallics 1990, 9, 1106.
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32. -1, The numbering scheme of 3 is equation presented
33. The volatile portion of the solution contained mostly unreacted acetylene and only a trace amount of acetylene homooligomers as analyzed by GC-MS.
34. -1) matched well with the previously reported values of trans-polyacetylene: (a) Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 11. (b) Landon, S. J.; Shulman, P. M.; Geoffroy, G. L. J. Am. Chem. Soc. 1985, 107, 6739.
35. -1) matched well with the previously reported values of trans-polyacetylene: (a) Ito, T.; Shirakawa, H.; Ikeda, S. J. Polym. Sci., Polym. Chem. Ed. 1974, 12, 11. (b) Landon, S. J.; Shulman, P. M.; Geoffroy, G. L. J. Am. Chem. Soc. 1985, 107, 6739.
36. 3, R(F) = 4.77% for 2746 observed independent reflections (2 ≤ 2θ ≤ 22.5°).
37. 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. (b) Bianchini, C.; Caulton, K. G.; Folting, K.; Meli, A.; Peruzzini, M.; Polo, A.; Vizza, F. J. Am. Chem. Soc. 1992, 114, 7290. (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. (d) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 709, 6525.
38. 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. (b) Bianchini, C.; Caulton, K. G.; Folting, K.; Meli, A.; Peruzzini, M.; Polo, A.; Vizza, F. J. Am. Chem. Soc. 1992, 114, 7290. (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. (d) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 709, 6525.
39. 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. (b) Bianchini, C.; Caulton, K. G.; Folting, K.; Meli, A.; Peruzzini, M.; Polo, A.; Vizza, F. J. Am. Chem. Soc. 1992, 114, 7290. (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. (d) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 709, 6525.
40. 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. (b) Bianchini, C.; Caulton, K. G.; Folting, K.; Meli, A.; Peruzzini, M.; Polo, A.; Vizza, F. J. Am. Chem. Soc. 1992, 114, 7290. (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. (d) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 709, 6525.
41. 1H NMR.
42. 2 hydrogen, we cannot rigorously rule out this mechanism at this time.