Ruthenium complexes bearing η5-pyrazolato ligands

Journal of the American Chemical Society

Volumn 121, Issue 18, 1999, Pages 4536-4537

  Perera, Jayani R ^a   Heeg, Mary Jane ^a   Schlegel, H Bernhard ^a   Winter, Charles H ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND; PYRAZOLE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; MOLECULAR DYNAMICS; SYNTHESIS;

EID: 0033549132     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990109a     Document Type: Article

References (44)

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23. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
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25. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
26. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
27. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
28. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
29. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
30. 5-pyrrolyl ligands, see: Rakowski DuBois, M.; Parker, K. G.; Ohman, C.; Noll, B. C. Organometallics 1997, 16, 2325. Janiak, C.; Kuhn, N. Adv. Nitrogen Heterocycl. 1996, 2, 179. Schumann, H.; Rosenthal, E. C. E.; Winterfeld, J.; Kociok-Köhn, G. J. Organomet. Chem. 1995, 495, C12. Schumann, H.; Winterfeld, J.; Hemling, H.; Kuhn, N. Chem. Ber. 1993, 126, 2657. Kelly, W. J.; Parthun, W. E. Organometallics 1992, 11, 4348. Kuhn, N.; Henkel, G.; Stubenrauch, S. J. Chem. Soc., Chem. Commun. 1992, 760. Kuhn, N.; Köckerling, M.; Stubenbrauch, S.; Bläser, D.; Boese, R. J. Chem. Soc., Chem. Commun. 1991, 1368. Kuhn, N.; Kuhn, A.; Lampe, E.-M. Chem. Ber. 1991, 124, 997. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1989, 28, 342. Kuhn, N.; Horn, E.-M.; Boese, R.; Augart, N. Angew. Chem., Int. Ed. Engl. 1988, 27, 1368. Kuhn, N.; Horn, E.-M.; Zauder, E.; Bläser, D.; Boese, R. Angew. Chem., Int. Ed. Engl. 1988, 27, 579. Efraty, A.; Jubran, N. Inorg. Chim. Acta 1980, 44, L191.
31. Fagan, P. J.; Ward, M. D.; Calabrese, J. C. J. Am. Chem. Soc. 1989, 111, 1698.
32. Preparative procedures, spectral data, and analytical data for 1-3 are contained in the Supporting Information.
33. The cyclic voltammetry experiments were conducted with a BAS-100 electrochemical analyzer using a glassy carbon working electrode and a Ag/AgCl reference electrode. The solvent was acetonitrile containing 0.1 M tetrabutylammonium hexafluorophosphate. The sweep rate was 100 mV/s. The reported potential values are for irreversible oxidations. The oxidation potentials are relative to an internal ferrocene standard (E° = 0.31 V): Gagne, R. R.; Koval, C. H.; Lisensky, G. C. Inorg. Chem. 1980, 19, 2854.
34. Gassman, P. G.; Winter, C. H. J. Am. Chem. Soc. 1988, 110, 6131.
35. -3, R(F) = 3.00% for 3479 observed reflections (4.92° ≤ 2Θ ≤ 56.60°). All non-hydrogen atoms in 1 were refined with anisotropic displacement parameters. Full data for the X-ray crystal structure determination of 1 are enclosed in the Supporting Information. The X-ray crystal structure of 2 was also determined and reveals a sandwich structure similar to that of 1. Complete details will be reported in a later full paper.
36. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
37. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
38. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
39. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
40. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
41. Computed with Gaussian 98 (Frisch, M. J.; et al., Gaussian, Inc., Pittsburgh, PA, 1998). The LANL2DZ basis set and pseudopotentials (Hay, P. J.; Wadl, W. R. J. Chem. Phys. 1985, 82, 270, 284, 299) were used with the B3LYP (Becke, A. D. Phys. Rev. A 1988, 38, 3098; Lee, C.; Yang W.; Parr, R. D. Phys. Rev. B 1988, 37, 785; Becke, A. D. J. Chem. Phys. 1993, 98, 5648) hybrid density functional method. Geometries were fully optimized using redundant internal coordinates (Peng, C.; Ayala, P. Y.; Schlegel, H. B.; Frisch, M. J. J. Comput. Chem. 1996, 17, 49.
42. Seel, F.; Sperber, V. J. Organomet. Chem. 1968, 14, 405.
43. Recent work from the Fu group has demonstrated that azametallocenes can function as nucleophilic catalysts in a variety of organic transformations. For leading references, see: Garrett, C. H.; Fu, G. C. J. Am. Chem. Soc. 1998, 120, 7479.
44. Initial reactivity studies have demonstrated that 1 can be mercurated and forms an adduct with boron trifluoride. Reactivity studies of 1-3 are ongoing.