An efficient and chemoselective iron catalyst for the hydrogenation of ketones

Journal of the American Chemical Society

Volumn 129, Issue 18, 2007, Pages 5816-5817

  Casey, Charles P ^a   Guan, Hairong ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLETHANOL; ACETOPHENONE; ALDEHYDE; IRON; IRON COMPLEX; KETONE; TOLUENE;

ARTICLE; CATALYST; HYDROGENATION; IRON BINDING CAPACITY; KINETICS; NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; STOICHIOMETRY;

CATALYSIS; HYDROGEN; IRON; KETONES;

EID: 34248588275     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071159f     Document Type: Article

References (27)

1. For examples, see: (a) Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.
2. (b) Ikariya, T.; Murata, K.; Noyori, R. Org. Biomol. Chem. 2006, 4, 393.
3. (c) Shvo, Y.; Czarkie, D.; Rahamim, Y.; Chodosh, D. F. J. Am. Chem. Soc. 1986, 108, 7400.
4. (d) Casey, C. P.; Singer, S. W.; Powell, D. R.; Hayashi, R. K.; Kavana, M. J. Am. Chem. Soc. 2001, 123, 1090.
5. Iron hydrogenase enzymes: (a) Peters, J. W.; Lanzilotta, W. N.; Lemon, B. J.; Seefeldt, L. C. Science 1998, 282, 1853.
6. (b) Nicolet, Y.; Piras, C.; Legrand, P.; Hatchikian, C. E.; Fontecilla-Camps, J. C. Structure 1999, 7, 13.
7. (c) Fan, H.-J.; Hall, M. B. J. Am. Chem. Soc. 2001, 123, 3828.
8. For Fe catalysts for selective alkene hydrogenation, see: (a) Schroeder, M. A.; Wrighton, M. S. J. Am. Chem. Soc. 1976, 98, 551.
9. (b) Bart, S. C.; Lobkovsky, E.; Chirik, P. J. J. Am. Chem. Soc. 2004, 126, 13794.
10. (c) Daida, E. J.; Peters, J. C. Inorg. Chem. 2004, 43, 7414.
11. 2. Radhi, M. A.; Markó, L. J. Organomet. Chem. 1984, 262, 359.
12. (a) Casey, C. P.; Johnson, J. B. J. Am. Chem. Soc. 2005, 127, 1883.
13. (b) Casey, C. P.; Bikzhanova, G. A.; Cui, Q.; Guzei, I. A. J. Am. Chem. Soc. 2005, 127, 14062.
14. (c) Casey, C. P.; Bikzhanova, G. A.; Guzei, I. A. J. Am. Chem. Soc. 2006, 128, 2286.
15. Hydride 1 was isolated as an intermediate in the synthesis of a cyclopentadienone from a dialkyne. Knölker, H.-J.; Baum, E.; Goesmann, H.; Klauss, R. Angew. Chem., Int. Ed. 1999, 38, 2064.
16. Early attempts to synthesize or spectroscopically observe analogous ruthenium alcohol complexes failed. Casey, C. P.; Bikzhanova, G. A.; Bäckvall, J.-E.; Johansson, L.; Park, J.; Kim, Y. H. Organometallics 2002, 21, 1955.
17. Pearson, A. J.; Shively, R. J., Jr.; Dubbert, R. A. Organometallics 1992, 11, 4096.
18. For an alternative mechanism involving coordination of the substrate and slippage of the Cp ring, see: Samec, J. S. M.; Ell, A. H.; Åberg, J. B.; Privalov, T.; Eriksson, L.; Bäckvall, J.-E. J. Am. Chem. Soc. 2006, 128, 14293.
19. -1 in toluene) was observed.
20. 2 pressure (see Supporting Information).
21. 13 1 neither hydrogenated nor isomerized 4-phenyl-1-butene.
22. (a) Bolm, C.; Legros, J.; Le Paih, J.; Zani, L. Chem. Rev. 2004, 104, 6217.
23. (b) Long, G. T.; Weitz, E. J. Am. Chem. Soc. 2000, 122, 1431 and references therein.
24. 3 in methanol. Brunet, J.-J.; Taillefer, M. J. Organomet. Chem. 1988, 348, C5.
25. The reduction of aromatic nitro compounds to anilines is catalyzed by iron complexes. Cann, K.; Cole, T.; Slegeir, W.; Pettit, R. J. Am. Chem. Soc. 1978, 100, 3969.
26. See Supporting Information.
27. For Ru-catalyzed transfer hydrogenation of ketones, see: Santosh Laxmi, Y. R.; Bäckvall, J.-E. Chem. Commun. 2000, 611.