The ruthenium acetylide catalyzed cross-coupling reaction of terminal and internal alkynes: Isolation of a catalytically active β-agostic intermediate species

Organometallics

Volumn 17, Issue 15, 1998, Pages 3158-3160

  Yi, Chae S ^a   Liu, Nianhong ^a  

^a MARQUETTE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001344076     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om980405g     Document Type: Article

References (37)

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3. Recent reviews: (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992. (b) Bönnemann, H.; Brijoux, W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol. 2, p 1102. (c) 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. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1990; Vol. 5.
4. Recent reviews: (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992. (b) Bönnemann, H.; Brijoux, W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol. 2, p 1102. (c) 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. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1990; Vol. 5.
5. Recent reviews: (a) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis, 2nd ed.; Wiley: New York, 1992. (b) Bönnemann, H.; Brijoux, W. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: New York, 1996; Vol. 2, p 1102. (c) 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. (d) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1995, 34, 259. (e) Schore, N. E. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1990; Vol. 5.
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17. See the Supporting Information for the spectroscopic data of 3 and 7.
18. CH values are 9-10 Hz for cis complexes and 15-16 Hz for trans complexes. For a detailed treatment, see: Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; Wiley: New York, 1988.
19. 45PRu: C, 72.01; H, 7.16. Found C, 71.89; H, 7.17.
20. For examples of metal-enynyl complexes in alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (c) Schäfer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
21. For examples of metal-enynyl complexes in alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (c) Schäfer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
22. For examples of metal-enynyl complexes in alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (c) Schäfer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
23. For examples of metal-enynyl complexes in alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (c) Schäfer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
24. For examples of metal-enynyl complexes in alkyne coupling reactions, see: (a) Yoshida, M.; Jordan, R. F. Organometallics 1997, 16, 4508. (b) Bianchini, C.; Innocenti, P.; Peruzzini, M.; Romerosa, A.; Zanobini, F. Organometallics 1996, 15, 272. (c) Schäfer, M.; Mahr, N.; Wolf, J.; Werner, H. Angew. Chem., Int. Ed. Engl. 1993, 32, 1315. (d) Wakatsuki, Y.; Yamazaki, H.; Kumegawa, N.; Satoh, T.; Satoh, J. Y. J. Am. Chem. Soc. 1991, 113, 9604. (e) Yasuda, T.; Kai, Y.; Yasuoka, N.; Kasai, N. Bull. Chem. Soc. Jpn. 1977, 50, 2888.
25. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
26. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
27. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
28. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
29. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
30. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
31. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
32. For recent examples of β-agostic alkyl complexes, see: (a) Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1 and references therein. (b) Brookhart, M.; Volpe, A. F., Jr.; Lincoln, D. M.; Horváth, I. T.; Millar, J. M. J. Am. Chem. Soc. 1990, 112, 5634. (c) Jordan, R. F.; Bradley, P. K.; Baenziger, N. C.; LaPointe, R. E. J. Am. Chem. Soc. 1990, 112, 1289. (d) Carmona, E.; Contreras, L.; Poveda, M. L.; Sánchez, L. J. J. Am. Chem. Soc. 1991, 113, 4322. (e) Lemke, F. R.; Szalda, D. J.; Bullock, R. M. J. Am. Chem. Soc. 1991, 113, 8466. (f) Brookhart, M.; Hauptman, E.; Lincoln, D. M. J. Am. Chem. Soc. 1992, 114, 10394. (g) Ogasawara, M.; Saburi, M. Organometallics 1994, 13, 1911. (h) Tanner, M. J.; Brookhart, M.; DeSimone, J. M. J. Am. Chem. Soc. 1997, 119, 7617.
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