Direct and transfer hydrogenation of ketones and imines with a ruthenium N-heterocyclic carbene complex

Advanced Synthesis and Catalysis

Volumn 347, Issue 4, 2005, Pages 591-594

  Burling, Suzanne ^a   Whittlesey, Michael K ^a   Williams, Jonathan M J ^a  

^a University of Bath Claverton Down   (United Kingdom)

Author keywords

Homogeneous catalysis; N heterocyclic carbenes; Ruthenium; Transfer hydrogenation

Indexed keywords

BASE; CARBENOID; IMIDAZOLE DERIVATIVE; IMINE; KETONE DERIVATIVE; RUTHENIUM COMPLEX;

ARTICLE; CATALYST; CHEMICAL REACTION; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 17144409059     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200404308     Document Type: Article

References (31)

1. a) G. Zassinovich, G. Mestroni, S. Gladiali, Chem. Rev. 1992, 92, 1051;
2. b) H.-U. Blaser, C. Malan, B. Pugin, F. Spindler, H. Steiner, M. Studer, Adv. Synth. Catal. 2003, 345, 103.
3. a) T. Naota, H. Takaya, S.-I. Murahashi, Chem. Rev. 1998, 98, 2599;
4. b) R. Noyori, S. Hashiguchi, Acc. Chem. Res. 1997, 30, 97;
5. c) M. J. Palmer, M. Wills, Tetrahedron: Asymmetry 1999, 10, 2045;
6. d) J.-E. Bäckvall, J. Organomet. Chem. 2002, 652, 105.
7. a) A. A. Danopoulos, S. Winston, W. B. Motherwell, Chem. Commun. 2002, 1376;
8. b) J. Louie, C. W. Bielawski, R. H. Grubbs, J. Am. Chem. Soc. 2001, 123, 11312;
9. c) M. Poyatos, J. A. Mata, E. Falomir, R. H. Crabtree, E. Peris, Organometallics 2003, 22, 1110.
10. 3 is referred to in this paper.
11. R. F. R. Jazzar, S. A. Macgregor, M. F. Mahon, S. P. Richards, M. K. Whittlesey, J. Am. Chem. Soc. 2002, 124, 4944.
12. V. Rautenstrauch, X. Hoang-Cong, R. Churland, K. Abdur-Rashid, R. H. Morris, Chem. Eur. J. 2003, 9, 4954.
13. S. Hashiguchi, A. Fujii, K-J. Haack, K. Matsumura, T. Ikariya, R. Noyori, Angew. Chem. Int. Ed. 1997, 36, 288.
14. The equilibrium position reached depends on the relative oxidation potentials of the carbonyl compounds involved: H. Adkins, R. M. Elofson, A. G. Rossow, C. C. Robinson, J. Am. Chem. Soc. 1949, 71, 3622.
15. 1H NMR after work-up.
16. Reduction of acetophenone 4a to phenethyl alcohol 3a was performed on a synthetic scale (1 mmol) with 70% conversion observed after 6 hours at 50°C.
17. a) F. Porta, S. Cenini, S. Giordano, M. Pizzotti, J. Organomet. Chem. 1978, 150, 261;
18. b) J. M. Bray, R. J. Mawby, J. Chem. Soc. Dalton. Trans. 1987, 2989;
19. c) M. Helliwell, J. D. Vessey, R. J. Mawby, J. Chem. Soc. Dalton. Trans. 1994, 1193.
20. a) B. Schmidt, Chem. Commun. 2004, 742;
21. b) S. H. Hong, M. W. Day, R. H. Grubbs, J. Am. Chem. Soc. 2004, 126, 7414;
22. c) D. Banti, J. C. Mol, J. Organomet. Chem. 2004, 689, 3113.
23. a) J. S. M. Samec, J.-E. Bäckvall, Chem. Eur. J. 2002, 8, 2955;
24. b) G. Z. Wang, J.-E. Bäckvall, J. Chem. Soc. Chem. Commun. 1992, 980;
25. c) E. Mizushima, M. Yamaguchi, T. Yamagishi, Chem. Lett. 1997, 26, 237;
26. d) M. Albrecht, R. H. Crabtree, J. Mata, E. Peris, Chem. Commun. 2002, 32;
27. e) J. R. Miecznikowski, R. H. Crabtree, Polyhedron 2004, 23, 2857.
28. a) N. Uematsu, A. Fujii, S. Hashiguchi, T. Ikariya, R. Noyori, J. Am. Chem. Soc. 1996, 118, 4916;
29. b) S. Kobayashi, H. Ishitani, Chem. Rev. 1999, 99, 1069;
30. c) J. Mao, D. C. Baker, Org. Lett. 1999, 1, 841;
31. d) S. Kuhl, R. Schneider, Y. Fort, Organometallics 2003, 22, 4184.