A new class of tethered-arene ruthenium(II) complexes with pendant P and C donor atoms: Synthesis of η6:η1:η1 phosphonio-azabutadienyl ruthenabicycles via allenylidene intermediates

Chemical Communications

Volumn , Issue 16, 2004, Pages 1820-1821

  Cadierno, Victorio ^a   Díez, Josefina ^a   García Álvarez, Joaquín ^a   Gimeno, José ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIPHENYL 2 PROPYN 1 OL; CARBENOID; DICHLOROMETHANE; IMINOPHOSPHORANE COMPLEX; LIGAND; PHOSPHORANE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RUTHENIUM CARBON LIGAND; RUTHENIUM COMPLEX; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CYCLOADDITION; LIGAND BINDING; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STOICHIOMETRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 4644309502     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b404971c     Document Type: Article

References (22)

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3. M. I. Bruce, Chem. Rev., 1998, 98, 2797; V. Cadierno, M. P. Gamasa and J. Gimeno, Eur. J. Inorg. Chem., 2001, 571.
4. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
5. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
6. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
7. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
8. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
9. Ruthenium(II) allenylidene complexes have shown to be active precatalysts in: (a) ROMP: R. Castarlenas and P. H. Dixneuf, Angew. Chem., Int. Ed., 2003, 42, 4524; (b) RCM: M. Bassetti, F. Centola, D. Sémeril, C. Bruneau and P. H. Dixneuf, Organometallics, 2003, 22, 4459; (c) Dimerization of tin hydrides: S. M. Maddock and M. G. Finn, Angew. Chem., Int. Ed., 2001, 40, 2138; (d) Propargylic substitutions: Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (e) Allenylidene-ene reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2003, 125, 6060; (f) Cycloaddition reactions: Y. Nishibayashi, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 7900.
10. T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067; V. Ritleng, C. Stirling and M. Pfeffer, Chem. Rev., 2002, 102, 1731.
11. T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067; V. Ritleng, C. Stirling and M. Pfeffer, Chem. Rev., 2002, 102, 1731.
12. T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599; B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067; V. Ritleng, C. Stirling and M. Pfeffer, Chem. Rev., 2002, 102, 1731.
13. V. Cadierno, S. Conejero, M. P. Gamasa and J. Gimeno, Dalton Trans., 2003, 3060 and references therein.
14. 6-arene)-Ru(II) complexes containing pendant N,N- and N,O-donor arms have been recently reported: J. Hannedouche, G. J. Clarkson and M. Wills, J. Am. Chem. Soc., 2004, 126, 986.
15. We have described the synthesis and hemilabile behaviour of complexes 1a-b and 3-4: V. Cadierno, J. Díez, S. E. García-Garrido, S. García-Granda and J. Gimeno, J. Chem. Soc., Dalton Trans., 2002, 1465; V. Cadierno, P. Crochet, J. García-Álvarez, S. E. García-Garrido and J. Gimeno, J. Organomet. Chem., 2002, 663, 32.
16. We have described the synthesis and hemilabile behaviour of complexes 1a-b and 3-4: V. Cadierno, J. Díez, S. E. García-Garrido, S. García-Granda and J. Gimeno, J. Chem. Soc., Dalton Trans., 2002, 1465; V. Cadierno, P. Crochet, J. García-Álvarez, S. E. García-Garrido and J. Gimeno, J. Organomet. Chem., 2002, 663, 32.
17. 4], are known: (a) D. J. Bernad, M. A. Esteruelas, A. M. López, J. Modrego, M. C. Puerta and P. Valerga, Organometallics, 1999, 18, 4995; (b) M. L. Buil, M. A. Esteruelas, A. M. López and E. Oñate, Organometallics, 2003, 22, 162.
18. 4], are known: (a) D. J. Bernad, M. A. Esteruelas, A. M. López, J. Modrego, M. C. Puerta and P. Valerga, Organometallics, 1999, 18, 4995; (b) M. L. Buil, M. A. Esteruelas, A. M. López and E. Oñate, Organometallics, 2003, 22, 162.
19. The P(1)-N(1) distance (1.638(6) Å) shows also the expected value for a P-N single bond. See for example: F. H. Allen, O. Kennard, D. G. Watson, A. G. Orpen, L. Brammer and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1. These structural parameters seem to rule out any important contribution from the carbenic resonance form: 10 See for example: H. Butenschon, Chem. Rev., 2000, 100, 1527; J. W. Faller and D. G. D'Alliessi, Organometallics, 2003, 22, 2749; B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P. H. Dixneuf, Chem. Eur. J., 2003, 9, 2323.
20. The P(1)-N(1) distance (1.638(6) Å) shows also the expected value for a P-N single bond. See for example: F. H. Allen, O. Kennard, D. G. Watson, A. G. Orpen, L. Brammer and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1. These structural parameters seem to rule out any important contribution from the carbenic resonance form: 10 See for example: H. Butenschon, Chem. Rev., 2000, 100, 1527; J. W. Faller and D. G. D'Alliessi, Organometallics, 2003, 22, 2749; B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P. H. Dixneuf, Chem. Eur. J., 2003, 9, 2323.
21. The P(1)-N(1) distance (1.638(6) Å) shows also the expected value for a P-N single bond. See for example: F. H. Allen, O. Kennard, D. G. Watson, A. G. Orpen, L. Brammer and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1. These structural parameters seem to rule out any important contribution from the carbenic resonance form: 10 See for example: H. Butenschon, Chem. Rev., 2000, 100, 1527; J. W. Faller and D. G. D'Alliessi, Organometallics, 2003, 22, 2749; B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P. H. Dixneuf, Chem. Eur. J., 2003, 9, 2323.
22. The P(1)-N(1) distance (1.638(6) Å) shows also the expected value for a P-N single bond. See for example: F. H. Allen, O. Kennard, D. G. Watson, A. G. Orpen, L. Brammer and R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, S1. These structural parameters seem to rule out any important contribution from the carbenic resonance form: 10 See for example: H. Butenschon, Chem. Rev., 2000, 100, 1527; J. W. Faller and D. G. D'Alliessi, Organometallics, 2003, 22, 2749; B. Çetinkaya, S. Demir, I. Özdemir, L. Toupet, D. Sémeril, C. Bruneau and P. H. Dixneuf, Chem. Eur. J., 2003, 9, 2323.