Regioselective nucleophilic addition of triphenylphosphine to the nitrosylruthenium alkynyl complexes having a hydrotris(pyrazol-1-yl)borate: Formation of phosphonio-alkenyl, alkynyl, and allenyl species

Dalton Transactions

Volumn , Issue 5, 2005, Pages 930-937

  Nishimura, Yoshimasa ^a   Arikawa, Yasuhiro ^a   Inoue, Takanori ^a   Onishi, Masayoshi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; COMPLEXATION; CRYSTALLOGRAPHY; KETONES; NUCLEAR MAGNETIC RESONANCE; ORGANOMETALLICS; REACTION KINETICS; RUTHENIUM COMPOUNDS; SINGLE CRYSTALS; STRUCTURE (COMPOSITION); X RAY ANALYSIS;

ALKYNL COMPLEXES; ALLENYL SPECIES; CATALYTIC TRANSFORMATION; KETONYL SPECIES;

AROMATIC COMPOUNDS;

ALKADIENE; ALKENE; ALKYNE; ALLENE; BORON DERIVATIVE; NITRO DERIVATIVE; ORGANOPHOSPHORUS COMPOUND; PYRAZOLE DERIVATIVE; RUTHENIUM; TRIPHENYLPHOSPHINE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; X RAY CRYSTALLOGRAPHY;

ALKADIENES; ALKENES; ALKYNES; BORON COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; MODELS, CHEMICAL; NITRO COMPOUNDS; ORGANOPHOSPHORUS COMPOUNDS; PYRAZOLES; RUTHENIUM;

EID: 15344341890     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/b415483e     Document Type: Article

References (32)

1. (a)M. I. Bruce, Chem. Rev., 1991, 91, 197-257;
2. (b) M. I. Bruce, Chem Rev., 1998, 98, 2797-2858;
3. (c) D. Touchard and P. H. Dixneuf, Coord. Chem. Rev., 1998, 178-180, 409-429;
4. (d) M. C. Puerta and P. Valerga, Coord. Chem. Rev., 1999, 193-195, 977-1025.
5. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
6. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
7. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
8. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
9. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
10. For recent Ru-mediated reactions, see: (a) B. M. Trost, F. D. Toste and A. B. Pinkerton, Chem. Rev., 2001, 101, 2067-2096; (b) T. Naota, H. Takaya and S.-I. Murahashi, Chem. Rev., 1998, 98, 2599-2660; (c) C. Bruneau and P. H. Dixneuf, Acc. Chem. Res., 1999, 32, 311-323; (d) K. Kirchner, M. J. Calhorda, R. Schmid and L. F. Veiros, J. Am. Chem. Soc., 2003, 125, 11721-11729; (e) Y. Yamamoto, T. Arakawa, R. Ogawa and K. Itoh, J. Am. Chem. Soc., 2003, 125, 12143-12160; (f) Y. Nishibayashi, H. Imajiraa, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26-30, and references cited therein.
11. (a) M. Onishi, Bull. Chem. Soc. Jpn., 1991, 64, 3039-3045;
12. (b) For other hydrotris(pyrazolyl)borate ruthenium, see: C. Slugovc, R. Schmid and K. Kirchner, Coord. Chem. Rev., 1999, 185-186, 109-126.
13. Y. Arikawa, Y. Nishimura, H. Kawano and M. Onishi, Organometallics, 2003, 22, 3354-3356.
14. Y. Arikawa, Y. Nishimura, K. Ikeda and M. Onishi, J. Am. Chem. Soc., 2004, 126, 3706-3707.
15. V. Cadierno, M. P. Gamasa, J. Gimeno, J. Borge and S. García-Granda, Organometallics, 1997, 16, 3178-3187.
16. V. Cadierno, M. P. Gamasa, J. Gimeno, C. González-Bernardo, E. Pérez-Carreño and S. García-Granda, Organometallics, 2001, 20, 5177-5188.
17. Y. Yamamoto, K. Ogata, K. Kuge and K. Tatsumi, Inorg. Chem. Commun., 2002, 5, 862-864.
18. 2).
19. C. Slugovc, V. N. Sapunov, P. Wiede, K. Mereiter, R. Schmid and K. Kirchner, J. Chem. Soc., Dalton Trans., 1997, 4209-4216.
20. (a) J. P. Collman and L. S. Hegedus, in Principles and Applications of Organotransition Metal Chemistry, University Science Books, Mill Valley, CA, 1980;
21. (b) S. Komiya, in Synthesis of Organometallic Compounds. A Practical Guide, John Wiley & Sons, Chichester, 1997.
22. 4 was observed without any intermediates.
23. V. Cadierno, M. P. Gamasa, J. Gimeno, M. C. López-González, J. Borge and S. García-Granda, Organometallics, 1997, 16, 4453-4463.
24. V. Cadierno, S. Conejero, M. P. Gamasa, J. Gimeno, I. Asselberghs, S. Houbrechts, K. Clays, A. Persoons, J. Borge and S. Garcia-Granda, Organometallics, 1999, 18, 582-597.
25. E. Bustelo, M. J. Tenorio, M. C. Puerta and P. Valerga, Organometallics, 1999, 18, 4563-4573.
26. V. Cadierno, S. Conejero, M. P. Gamasa, J. Gimeno and M. A. Rodriguez, Organometallics, 2002, 21, 203-209.
27. M. A. Esteruelas, A. V. Gómez, A. M. López, J. Modrego and E. Oñate, Organometallics, 1998, 17, 5434-5436.
28. H. D. Hansen and J. H. Nelson, Organometallics, 2000, 19, 4740-4755.
29. For a comprehensive review on the reactivities of allenylidene metal complexes, see: V. Cadierno, M. P. Gamasa and J. Gimeno, Eur. J. Inorg. Chem., 2001, 571-591.
30. M. I. Bruce, B. W. Skelton, A. H. White and N. N. Zaitseva, J. Chem. Soc., Dalton Trans., 2001, 355-356.
31. M. Peruzzini, P. Barbaro, V. Bertolasi, C. Bianchini, I. de los Rios, N. Mantovani, L. Marvelli and R. Rossi, Dalton Trans., 2003, 4121-4131.
32. p, route (a) would precede route (b) when the γ-hydroxyalkynyl ligand contain a tertiary alcohol moiety, being independent of the steric factor at the γ-carbon (ref. 4).