Cyclometalated ruthenium(II) complexes as highly active transfer hydrogenation catalysts

Angewandte Chemie - International Edition

Volumn 43, Issue 27, 2004, Pages 3584-3588

  Baratta, Walter ^a   Da Ros, Paolo ^a   Del Zotto, Alessandro ^a   Sechi, Alessandra ^a   Zangrando, Ennio ^b   Rigo, Pierluigi ^a  

^a UNIVERSITY OF UDINE   (Italy)

^b UNIVERSITY OF TRIESTE   (Italy)

Author keywords

Cyclometalation; Homogeneous catalysis; Noncovalent interactions; P ligands; Ruthenium

Indexed keywords

ALCOHOLS; CATALYSTS; CRYSTAL STRUCTURE; HYDROGENATION; KETONES;

ELECTRON COMPLEX; PHOSPHANE GROUP;

RUTHENIUM COMPOUNDS;

ALCOHOL; KETONE; METHYL GROUP; PYRIDINE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL INTERACTION; CHEMICAL MODIFICATION; CHEMICAL REACTION KINETICS; COMPLEX FORMATION; CRYSTAL STRUCTURE; HYDROGENATION; QUANTITATIVE ANALYSIS; STOICHIOMETRY; X RAY DIFFRACTION;

EID: 4544336124     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454199     Document Type: Article

References (46)

1. a) M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866; Angew. Chem. Int. Ed. 2001, 40, 3750;
2. a) M. Albrecht, G. van Koten, Angew. Chem. 2001, 113, 3866; Angew. Chem. Int. Ed. 2001, 40, 3750;
3. b) M. E. van der Boom, D. Milstein, Chem. Rev. 2003, 103, 1759;
4. c) J. T. Singleton, Tetrahedron 2003, 59, 1837;
5. d) M. Ohff, A. Ohff, M. E. van der Boom, D. Milstein, J. Am. Chem. Soc. 1997, 119, 11687;
6. e) F. Miyazaki, K. Yamaguchi, M. Shibasaky, Tetrahedron Lett. 1999, 40, 7379;
7. f) S. Gibson, D. F. Foster, G. R. Eastham, R. P. Tooze, D. J. Cole-Hamilton, Chem. Commun. 2001, 779;
8. g) M. Gupta, C. Hagen, W. C. Kaska, R. E. Cramer, C. M. Jensen, J. Am. Chem. Soc. 1997, 119, 840;
9. h) F. Liu, E. B. Pak, B. Singh, C. M. Jensen, A. S. Goldman, J. Am. Chem. Soc. 1999, 121, 4086;
10. i) P. Dani, T. Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem. 2000, 112, 759; Angew. Chem. Int. Ed. 2000, 39, 743.
11. P. Dani, T Karlen, R. A. Gossage, S. Gladiali, G. van Koten, Angew. Chem. 2000, 112, 759; Angew. Chem. Int. Ed. 2000, 39, 743.
12. a) A. D. Ryabov, Chem. Rev. 1990, 90, 403;
13. b) I. Omae, Coord. Chem. Rev. 1980, 32, 235.
14. a) W. A. Herrmann, C. Brossmer, C.-P. Reisinger, T. H. Riermeier, K. Öfele, M. Beller, Chem. Eur. J. 1997, 3, 1357;
15. b) V. P. W. Böhm, W. A. Herrmann, Chem. Eur. J. 2001, 7, 4191;
16. c) J. Dupont, M. Pfeffer, J. Spencer, Eur. J. Inorg. Chem. 2001, 1917.
17. T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599.
18. a) L. N. Lewis, J. Am. Chem. Soc. 1986, 168, 743;
19. b) L. N. Lewis, J. F. Smith, J. Am. Chem. Soc. 1986, 108, 2728.
20. W. Baratta, E. Herdtweck, P. Rigo, Angew. Chem. 1999, 111, 1733; Angew. Chem. Int. Ed. 1999, 38, 1629.
21. W. Baratta, E. Herdtweck, P. Rigo, Angew. Chem. 1999, 111, 1733; Angew. Chem. Int. Ed. 1999, 38, 1629.
22. W. Baratta, S. Stoccoro, A. Doppiu, E. Herdtweck, A. Zucca, P. Rigo, Angew. Chem. 2003, 115, 109; Angew. Chem. Int. Ed. 2003, 42, 105.
23. W. Baratta, S. Stoccoro, A. Doppiu, E. Herdtweck, A. Zucca, P. Rigo, Angew. Chem. 2003, 115, 109; Angew. Chem. Int. Ed. 2003, 42, 105.
24. W. Baratta, E. Herdtweck, P. Martinuzzi, P. Rigo, Organometallics 2001, 20, 305.
25. a) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 1992, 92, 1051;
26. b) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97;
27. c) J. E. Bäckvall, J. Organomet. Chem. 2002, 652, 105;
28. d) S. Gladiali, G. Mestroni in Transition Metals for Organic Synthesis, Vol. 2 (Eds.: M. Beller, C. Bolm), Wiley-VCH, Weinheim, 1998, p. 97.
29. 2Ru: C 66.2, H 5.0; found: C 65.9, H 5.0.
30. Kα, radiation (λ = 0.71073 Å).
31. Kα. radiation (λ = 0.71073 Å). CCDC-224572 (2) and CCDC-224573 (3) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB21EZ, UK; fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk).
32. 2OPRu. C 57.7, H 4.7, N 5.0; found: C 57.3, H 4.6, N 5.0.
33. a) R. L. Chowdhury, J. E. Bäckvall, J. Chem. Soc. Chem. Commun. 1991, 1063;
34. b) H. Yang, M. Alvarez, N. Lugan, R. Mathieu, J. Chem. Soc. Chem. Commun. 1995, 1721;
35. c) H. Yang, M. Alvarez-Gressier, N. Lugan, R. Mathieu, Organometallics 1997, 16, 1401;
36. d) P. Crochet, J. Gimeno, S. García-Granada, J. Borge, Organometallics 2001, 20, 4369.
37. T. Ohkuma, M. Koizumi, H. Ikehira, T. Yokozawa, R. Noyori, Org. Lett. 2000, 2, 659.
38. a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997, 36, 285;
39. a) K.-J. Haack, S. Hashiguchi, A. Fujii, T. Ikariya, R. Noyori, Angew. Chem. 1997, 109, 297; Angew. Chem. Int. Ed. Engl. 1997, 36, 285;
40. A. Aranyos, G. Csjernyik, K. J. Szabó, J. E. Bäckvall, Chem. Commun. 1999, 351.
41. a) M. Yamakawa, H. Ito, R. Noyori, J. Am. Chem. Soc. 2000, 122, 1466;
42. b) K. Abdur-Rashid, S. E. Clapham, A. Hadzovic, J. N. Harvey, A. J. Lough, R. H. Morris, J. Am. Chem. Soc. 2002, 124 15104;
43. c) V. Rautenstrauch, X. Hoang-Cong, R. Churlaud, K. Abdur-Rashid, R. H. Morris, Chem. Eur. J. 2003, 9, 4954.
44. a) E. Mizushima, H. Ohi, M. Yamaguchi, T. Yamagishi, J. Mol. Catal. A 1999, 149, 43;
45. b) H. Brunner, M. Niemetz, Monatsh. Chem. 2002, 133, 115;
46. c) H. Brunner, F. Henning, M. Weber, Tetrahedron: Asymmetry 2002, 13, 37.