[Ru(η3-2-C3H4Me)(CO)(dppf)][SbF 6]: A mononuclear 16e- ruthenium(II) catalyst for propargylic substitution and isomerization of HC≡CCPh2(OH)

Chemical Communications

Volumn , Issue 23, 2004, Pages 2716-2717

  Cadierno, Victorio ^a   Díez, Josefina ^a   García Garrido, Sergio E ^a   Gimeno, José ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; RUTHENIUM;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERIZATION; MOLECULAR INTERACTION; PHASE TRANSITION; REACTION ANALYSIS; STOICHIOMETRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 11144277521     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b410812d     Document Type: Article

References (22)

1. For reviews on the Nicholas reaction see: K. M. Nicholas, Acc. Chem. Res., 1987, 20, 207; J. R. Green, Curr. Org. Chem., 2001, 5, 809; B. J. Teobald, Tetrahedron, 2002, 58, 4133.
2. For reviews on the Nicholas reaction see: K. M. Nicholas, Acc. Chem. Res., 1987, 20, 207; J. R. Green, Curr. Org. Chem., 2001, 5, 809; B. J. Teobald, Tetrahedron, 2002, 58, 4133.
3. For reviews on the Nicholas reaction see: K. M. Nicholas, Acc. Chem. Res., 1987, 20, 207; J. R. Green, Curr. Org. Chem., 2001, 5, 809; B. J. Teobald, Tetrahedron, 2002, 58, 4133.
4. Cu(I)-, Ti(IV)- and Ir(I)-catalyzed nucleophilic substitution of propargylic esters with alcohols, amines, amides and enoxysilanes are known: Y. Imada, M. Yuasa, I. Nakamura and S.-I. Murahashi, J. Org. Chem., 1994, 59, 2282; R. Mahrwald and S. Quint, Tetrahedron, 2000, 56, 7463; R. Mahrwald and S. Quint, Tetrahedron Lett., 2001, 42, 1655; R. Mahrwald, S. Quint and S. Scholtis, Tetrahedron, 2002, 58, 9847; I. Matsuda, K.-I. Komori and K. Itoh, J. Am. Chem. Soc., 2002, 124, 9072.
5. Cu(I)-, Ti(IV)- and Ir(I)-catalyzed nucleophilic substitution of propargylic esters with alcohols, amines, amides and enoxysilanes are known: Y. Imada, M. Yuasa, I. Nakamura and S.-I. Murahashi, J. Org. Chem., 1994, 59, 2282; R. Mahrwald and S. Quint, Tetrahedron, 2000, 56, 7463; R. Mahrwald and S. Quint, Tetrahedron Lett., 2001, 42, 1655; R. Mahrwald, S. Quint and S. Scholtis, Tetrahedron, 2002, 58, 9847; I. Matsuda, K.-I. Komori and K. Itoh, J. Am. Chem. Soc., 2002, 124, 9072.
6. Cu(I)-, Ti(IV)- and Ir(I)-catalyzed nucleophilic substitution of propargylic esters with alcohols, amines, amides and enoxysilanes are known: Y. Imada, M. Yuasa, I. Nakamura and S.-I. Murahashi, J. Org. Chem., 1994, 59, 2282; R. Mahrwald and S. Quint, Tetrahedron, 2000, 56, 7463; R. Mahrwald and S. Quint, Tetrahedron Lett., 2001, 42, 1655; R. Mahrwald, S. Quint and S. Scholtis, Tetrahedron, 2002, 58, 9847; I. Matsuda, K.-I. Komori and K. Itoh, J. Am. Chem. Soc., 2002, 124, 9072.
7. Cu(I)-, Ti(IV)- and Ir(I)-catalyzed nucleophilic substitution of propargylic esters with alcohols, amines, amides and enoxysilanes are known: Y. Imada, M. Yuasa, I. Nakamura and S.-I. Murahashi, J. Org. Chem., 1994, 59, 2282; R. Mahrwald and S. Quint, Tetrahedron, 2000, 56, 7463; R. Mahrwald and S. Quint, Tetrahedron Lett., 2001, 42, 1655; R. Mahrwald, S. Quint and S. Scholtis, Tetrahedron, 2002, 58, 9847; I. Matsuda, K.-I. Komori and K. Itoh, J. Am. Chem. Soc., 2002, 124, 9072.
8. Cu(I)-, Ti(IV)- and Ir(I)-catalyzed nucleophilic substitution of propargylic esters with alcohols, amines, amides and enoxysilanes are known: Y. Imada, M. Yuasa, I. Nakamura and S.-I. Murahashi, J. Org. Chem., 1994, 59, 2282; R. Mahrwald and S. Quint, Tetrahedron, 2000, 56, 7463; R. Mahrwald and S. Quint, Tetrahedron Lett., 2001, 42, 1655; R. Mahrwald, S. Quint and S. Scholtis, Tetrahedron, 2002, 58, 9847; I. Matsuda, K.-I. Komori and K. Itoh, J. Am. Chem. Soc., 2002, 124, 9072.
9. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
10. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
11. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
12. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
13. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
14. See for example: (a) Y. Nishibayashi, I. Wakiji and M. Hidai, J. Am. Chem. Soc., 2000, 122, 11019; (b) Y. Nishibayashi, I. Wakiji, Y. Ishii, S. Uemura and M. Hidai, J. Am. Chem. Soc., 2001, 123, 3393; (c) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Am. Chem. Soc., 2002, 124, 11846; (d) Y. Nishibayashi, G. Onodera, Y. Inada, M. Hidai and S. Uemura, Organometallics, 2003, 22, 873; (e) Y. Nishibayashi, H. Imajima, G. Onodera, M. Hidai and S. Uemura, Organometallics, 2004, 23, 26; (f) Y. Nishibayashi, M. Yoshikawa, Y. Inada, M. Hidai and S. Uemura, J. Org. Chem., 2004, 69, 3408.
15. For general reviews on the chemistry of allenylidene complexes see: M. I. Bruce, Chem. Rev., 1998, 98, 2797; V. Cadierno, M. P. Gamasa and J. Gimeno, Eur. J. Inorg. Chem., 2001, 571.
16. For general reviews on the chemistry of allenylidene complexes see: M. I. Bruce, Chem. Rev., 1998, 98, 2797; V. Cadierno, M. P. Gamasa and J. Gimeno, Eur. J. Inorg. Chem., 2001, 571.
17. 2]: V. Cadierno, S. Conejero, M. P. Gamasa and J. Gimeno, Dalton Trans., 2003, 3060 and references therein.
18. 2 = COD) have been found to catalyze the S-propargylation of thiols with internal propargylic carbonates via (σ-propargyl)-ruthenium intermediates: T. Kondo, Y. Kanda, A. Baba, K. Fukuda, A. Nakamura, K. Wada, Y. Morisaki and T. Mitsudo, J. Am. Chem. Soc., 2002, 124, 12960.
19. V. Cadierno, P. Crochet, J. Díez, S. E. García-Garrido, J. Gimeno and S. García-Granda, Organometallics, 2003, 22, 5226.
20. 2O) has been recently reported (disubstituted propargylic alcohols do not react at all): T. Suzuki, M. Tokunaga and Y. Wakatsuki, Tetrahedron Lett., 2002, 43, 7531;
21. 2H/PTSA catalytic system is known: M. Picquet, A. Fernández, C. Bruneau and P. H. Dixneuf, Eur. J. Org. Chem., 2000, 2361.
22. 2) in 67% yield after 6 h (an uncharacterised by-product is also formed in ca. 30% yield).