Transfer hydrogenation of ketones with 2-propanol and Raney® nickel

Synthetic Communications

Volumn 37, Issue 16, 2007, Pages 2787-2791

  Mebane, Robert C ^a   Holte, Kimberly L ^a   Gross, Benjamin H ^a  

^a UNIVERSITY OF TENNESSEE AT CHATTANOOGA   (United States)

Author keywords

Ketone reduction; Raney nickel; Transfer hydrogenation

Indexed keywords

2 PROPANOL; ALCOHOL; ALDEHYDE; ALKENE DERIVATIVE; HYDROCHLORIC ACID; KETONE DERIVATIVE; NICKEL; NITRILE; PHENOL DERIVATIVE;

ARTICLE; CATALYSIS; HYDROGENATION; REDUCTION;

EID: 34547956468     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701481211     Document Type: Article

References (14)

1. Mebane, R. C.; Mansfield, A. J. Transfer hydrogenation of aldehydes with 2-propanol and Raney nickel. Synth. Commun. 2005, 35 (24), 3083-3086.
2. Smith, M. B. Organic Synthesis, 2nd Ed.; McGraw-Hill: New York, 2002; pp. 306-343.
3. Vijayalakshmi, P.; Subbarao, R. Hydrogenation of heptaldehyde to heptyl alcohol with nickel catalysts. J. Am. Oil Chem. Soc. 1993, 70, 435-436.
4. Mebane, R. C.; Jensen, D. R.; Rickerd, K. R.; Gross, B. H. Transfer hydrogenation of nitriles with 2-propanol and Raney nickel. Synth. Commun. 2003, 33 (19), 3373-3379.
5. Mebane, R. C.; Grimes, K. D.; Jenkins, S. R.; Deardorff, J. D.; Gross, B. H. Deiodination of iodolactones by transfer hydrogenolysis using Raney nickel and 2-propanol. Synth. Commun. 2002, 32 (13), 2049-2054.
6. Gross, B. H.; Mebane, R. C.; Armstrong, D. L. Transfer hydrogenolysis of aromatic alcohols using Raney catalysts and 2-propanol. Appl. Catal. A 2001, 219, 281-289.
7. Andrews, M. J.; Pillai, C. N. Hydrogen transfer reactions, part VII: Hydrogen transfer reactions catalyzed by Raney nickel. Indian J. Chem. 1978, 16B, 465-468.
8. Kuo, E.; Srivastava, S.; Cheung, C. K.; le Noble, W. J. Facile reduction of aromatic nitro compounds to anilines with 2-propanol and Raney nickel. Synth. Commun. 1985, 15 (7), 599-602.
9. Srivastava, S.; Minore, J.; Cheung, C. K.; le Noble, W. J. Reduction of aromatic rings by 2-propanol with Raney nickel catalysis. J. Org. Chem. 1985, 50, 394-396.
10. Gonikberg, E. M.; le Noble, W. J. Face selection in reductions of 5,7-diazaadamantane-2-one derivatives: Mutual influence of remote substitutents. J. Org. Chem. 1995, 60, 7751-7755.
11. Mitsui, S.; Saito, H.; Yamashita, M.; Kaminaga, M.; Senda, Y. Stereochemistry and mechanism of catalytic hydrogenation of substituted cyclohexanones. Tetrahedron 1973, 29, 1531-1539.
12. Brieger, G.; Nestrick, T. J. Catalytic transfer hydrogenation. Chem. Rev. 1974, 74, 567-580.
13. Freifelder, M. Practical Catalytic Hydrogenation; Wiley: New York, 1971; pp. 66-68.
14. Augustine, R. L. Heterogeneous Catalysis for the Synthetic Chemist; Marcel Dekker: New York, 1996; pp. 447-452.