Tandem olefin metathesis/hydrogenation at ambient temperature: Activation of ruthenium carbene complexes by addition of hydrides

Organic and Biomolecular Chemistry

Volumn 1, Issue 14, 2003, Pages 2512-2517

  Schmidt, Bernd ^a   Pohler, Michael ^a  

^a TU DORTMUND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CHEMICAL ACTIVATION; COMPLEXATION; HYDRIDES; HYDROGENATION; OLEFINS; THERMAL EFFECTS;

PRECURSORS;

RUTHENIUM COMPOUNDS;

EID: 0141841782     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b303441k     Document Type: Article

References (38)

1. Reviews: (a) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (b) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed., 1997, 36, 2036; (d) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3013.
2. Reviews: (a) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (b) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed., 1997, 36, 2036; (d) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3013.
3. Reviews: (a) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (b) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed., 1997, 36, 2036; (d) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3013.
4. Reviews: (a) S. K. Armstrong, J. Chem. Soc., Perkin Trans. 1, 1998, 371; (b) R. H. Grubbs and S. Chang, Tetrahedron, 1998, 54, 4413; (c) M. Schuster and S. Blechert, Angew. Chem., Int. Ed., 1997, 36, 2036; (d) A. Fürstner, Angew. Chem., Int. Ed., 2000, 39, 3013.
5. For applications in target molecule synthesis, see: (a) H. Mizutani, M. Watanabe and T. Honda, Tetrahedron, 2002, 58, 8929; (b) M. G. Organ, J.-L. Xu and B. N'Zemba, Tetrahedron Lett., 2002, 43, 8177; (c) A. Fürstner, F. Jeanjean and P. Razon, Angew. Chem., Int. Ed, 2002, 41, 2097; (d) D. E. Williams, K. S. Craig, B. Patrick, L. M. McHardy, R. van Soest, M. Roberge and R. J. Andersen, J. Org. Chem., 2002, 67, 245.
6. For applications in target molecule synthesis, see: (a) H. Mizutani, M. Watanabe and T. Honda, Tetrahedron, 2002, 58, 8929; (b) M. G. Organ, J.-L. Xu and B. N'Zemba, Tetrahedron Lett., 2002, 43, 8177; (c) A. Fürstner, F. Jeanjean and P. Razon, Angew. Chem., Int. Ed, 2002, 41, 2097; (d) D. E. Williams, K. S. Craig, B. Patrick, L. M. McHardy, R. van Soest, M. Roberge and R. J. Andersen, J. Org. Chem., 2002, 67, 245.
7. For applications in target molecule synthesis, see: (a) H. Mizutani, M. Watanabe and T. Honda, Tetrahedron, 2002, 58, 8929; (b) M. G. Organ, J.-L. Xu and B. N'Zemba, Tetrahedron Lett., 2002, 43, 8177; (c) A. Fürstner, F. Jeanjean and P. Razon, Angew. Chem., Int. Ed, 2002, 41, 2097; (d) D. E. Williams, K. S. Craig, B. Patrick, L. M. McHardy, R. van Soest, M. Roberge and R. J. Andersen, J. Org. Chem., 2002, 67, 245.
8. For applications in target molecule synthesis, see: (a) H. Mizutani, M. Watanabe and T. Honda, Tetrahedron, 2002, 58, 8929; (b) M. G. Organ, J.-L. Xu and B. N'Zemba, Tetrahedron Lett., 2002, 43, 8177; (c) A. Fürstner, F. Jeanjean and P. Razon, Angew. Chem., Int. Ed, 2002, 41, 2097; (d) D. E. Williams, K. S. Craig, B. Patrick, L. M. McHardy, R. van Soest, M. Roberge and R. J. Andersen, J. Org. Chem., 2002, 67, 245.
9. R. Grigg, V. Sridharan and M. York, Tetrahedron Lett., 1998, 39, 4139.
10. (a) J. Cossy, F. C. Bargiggia and S. BouzBouz, Org. Lett., 2003, 5, 459;
11. (b) J. Cossy, F. C. Bargiggia and S. BouzBouz, Tetrahedron Lett, 2002, 43, 6715.
12. The mechanism of the formation of ruthenium-hydride species from ruthenium carbene complexes and hydrogen has been investigated: S. D. Drouin, G. P. A. Yap and D. E. Fogg, Inorg. Chem., 2000, 39, 5412.
13. Applications to hydrogenation of ROMP or RCM products: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872; (b) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (c) S. D. Drouin, F. Zamanian and D. E. Fogg, Organometallics, 2001, 20, 5495; (d) P. Borsting and P. Nielsen, Chem. Commun., 2002, 2140; (e) A. Fürstner and A. Leitner, Angew, Chem., Int. Ed, 2003, 42, 308.
14. Applications to hydrogenation of ROMP or RCM products: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872; (b) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (c) S. D. Drouin, F. Zamanian and D. E. Fogg, Organometallics, 2001, 20, 5495; (d) P. Borsting and P. Nielsen, Chem. Commun., 2002, 2140; (e) A. Fürstner and A. Leitner, Angew, Chem., Int. Ed, 2003, 42, 308.
15. Applications to hydrogenation of ROMP or RCM products: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872; (b) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (c) S. D. Drouin, F. Zamanian and D. E. Fogg, Organometallics, 2001, 20, 5495; (d) P. Borsting and P. Nielsen, Chem. Commun., 2002, 2140; (e) A. Fürstner and A. Leitner, Angew, Chem., Int. Ed, 2003, 42, 308.
16. Applications to hydrogenation of ROMP or RCM products: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872; (b) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (c) S. D. Drouin, F. Zamanian and D. E. Fogg, Organometallics, 2001, 20, 5495; (d) P. Borsting and P. Nielsen, Chem. Commun., 2002, 2140; (e) A. Fürstner and A. Leitner, Angew, Chem., Int. Ed, 2003, 42, 308.
17. Applications to hydrogenation of ROMP or RCM products: (a) C. W. Bielawski, J. Louie and R. H. Grubbs, J. Am. Chem. Soc., 2000, 122, 12872; (b) J. Louie, C. W. Bielawski and R. H. Grubbs, J. Am. Chem. Soc., 2001, 123, 11312; (c) S. D. Drouin, F. Zamanian and D. E. Fogg, Organometallics, 2001, 20, 5495; (d) P. Borsting and P. Nielsen, Chem. Commun., 2002, 2140; (e) A. Fürstner and A. Leitner, Angew, Chem., Int. Ed, 2003, 42, 308.
18. A. E. Sutton, B. A. Seigal, D. F. Finnegan and M. L. Snapper, J. Am. Chem. Soc., 2002, 124, 13390.
19. B. Schmidt, Eur. J. Org. Chem., 2003, 816.
20. Recently, a study describing the formation of a ruthenium-carbonylhydride complex by alcoholysis of ruthenium carbene complexes appeared: M. B. Dinger and J. C. Mol, Organometallics, 2003, 22, 1089. A ruthenium hydride complex has previously been described as a by-product in the synthesis of catalysts for olefin metathesis: A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236.
21. Recently, a study describing the formation of a ruthenium-carbonylhydride complex by alcoholysis of ruthenium carbene complexes appeared: M. B. Dinger and J. C. Mol, Organometallics, 2003, 22, 1089. A ruthenium hydride complex has previously been described as a by-product in the synthesis of catalysts for olefin metathesis: A. Fürstner, L. Ackermann, B. Gabor, R. Goddard, C. W. Lehmann, R. Mynott, F. Stelzer and O. R. Thiel, Chem. Eur. J., 2001, 7, 3236.
22. B. Schmidt and H. Wildemann, Eur. J. Org. Chem., 2000, 3145.
23. B. Schmidt and H. Wildemann, J. Chem. Soc., Perkin Trans. 1, 2002, 1050. It has previously been reported that diallyl carbinols show comparatively low reactivity in RCM with catalyst A: D. L. J. Clive and H. Cheng, Chem. Commun., 2001, 605.
24. B. Schmidt and H. Wildemann, J. Chem. Soc., Perkin Trans. 1, 2002, 1050. It has previously been reported that diallyl carbinols show comparatively low reactivity in RCM with catalyst A: D. L. J. Clive and H. Cheng, Chem. Commun., 2001, 605.
25. B. Schmidt and M. Westhus, Tetrahedron, 2000, 56, 2421.
26. M. Scholl, S. Ding, C. W. Lee and R. H. Grubbs, Org. Lett., 1999, 1, 953.
27. (a) R. L. Snowden, S. M. Linder, B. L. Müller and K. H. Schulte, Heb. Chim. Acta, 1987, 70, 1858;
28. (b) J. Barluenga, J. Florez and M. Yus, J. Chem. Soc., Perkin Trans. 1, 1983, 3019;
29. (c) V. J. Bryan and T.-H. Chan, Tetrahedron Lett., 1997, 38, 6493;
30. (d) H. L. Yale, E. J. Pribyl, W. Braker, J. Bernstein and W. A. Lott, J. Am. Chem. Soc., 1950, 72, 3716;
31. (e) D. J. Wallace, P. G. Bulger, D. J. Kennedy, M. S. Ashwood, I. F. Cottrell and U.-H. Dolling, Synlett, 2001, 357;
32. (f) C. Kashima, X. C. Huang, Y. Harada and A. Hosomi, J. Org. Chem., 1993, 58, 793.
33. (a) H.-J. Schneider, N. Nguyen-Ba and F. Thomas, Tetrahedron, 1982, 38, 2327;
34. (b) T. Imamoto, T. Hatajima, N. Takiyama, T. Takeyama, Y. Kamiya and T. Yoshizawa, J. Chem. Soc., Perkin Trans. 1, 1991, 3127;
35. (c) V. Nyzam, C. Belaud, F. Zammattio and J. Villieras, Bull Soc. Chim. Fr., 1997, 134, 583;
36. (d) P. Le Gendre, T. Braun, C. Bruneau and P. H. Dixneuf, J. Org. Chem., 1996, 61, 8453;
37. (e) S. Celebi, D. A. Modarelli, S. Leyva and M. S. Platz, J. Am. Chem. Soc., 1993, 115, 8613;
38. (f) A. Inoue, H. Shinokubo and K. Ochima, Synlett, 1999, 1582.