Browse > Article
http://dx.doi.org/10.5012/bkcs.2003.24.11.1664

A Mild and Convenient Method for the Reduction of Carbonyl Compounds with NaBH4 in the Presence of Catalytic Amounts of MoCl5  

Zeynizadeh, Behzad (Department of Chemistry, Faculty of Sciences, Urmia University)
Yahyaei, Saiedeh (Department of Chemistry, Faculty of Sciences, Urmia University)
Publication Information
Bulletin of the Korean Chemical Society / v.24, no.11, 2003 , pp. 1664-1670 More about this Journal
Abstract
$NaBH_4$ with catalytic amounts of $MoCl_5$ can readily reduce a variety of carbonyl compounds such as aldehydes, ketones, acyloins, ${\alpha}$-diketones and conjugated enones to their corresponding alcohols in good to excellent yields. Reduction reactions were performed under aprotic condition in $CH_3CN$ at room temperature or reflux. In addition, the chemoselective reduction of aldehydes over ketones was accomplished successfully with this reducing system.
Keywords
Reduction; Sodium borohydride; $MoCl_5$; Carbonyl compounds; Alcohols;
Citations & Related Records
Times Cited By KSCI : 2  (Citation Analysis)
Times Cited By Web Of Science : 16  (Related Records In Web of Science)
Times Cited By SCOPUS : 18
연도 인용수 순위
1 Hudlicky,M. Reductions in Organic Chemistry; Ellis Horwood Ltd.:Chichester, 1984.
2 Hajos, A. Complex Hydrides and RelatedReducing Agents in Organic Chemistry; Elsevier: Amsterdam,1979.
3 Zeynizadeh, B. Bull. Chem. Soc. Jpn. 2003, 76, 317.   DOI   ScienceOn
4 Seyden-Penne, J. Reductions by the Alumino and Borohydridesin Organic Synthesis, 2nd Ed.; Wiley-VCH: 1997.
5 Rubin, M. B.; Ben-Bassat, J. M. Tetrahedron Lett. 1971, 3403.
6 Ho, T.-L.; Olah, G.A.Synthesis 1976, 815.
7 Mori, T.; Nakahara, T.; Nozaki, H. Can.J. Chem. 1969, 47, 3266.   DOI
8 Mayer, R.; Hiller, G.; Nitzschke, M.;Jentzsch, J. Angew. Chem. 1963, 75, 1011.   DOI
9 Firouzabadi, H.; Zeynizadeh, B. Bull. Chem. Soc. Jpn. 1997, 70,155.   DOI   ScienceOn
10 Zeynizadeh, B.; Faraji, F. Bull. Korean Chem. Soc. 2003, 24, 453.   DOI   ScienceOn
11 Firouzabadi, H.; Zeynizadeh, B. Iranian J. Sci. & Tech., Trans. A1995, 19, 103.
12 Brown, H. C.; Subba Rao, B. C. J. Am. Chem. Soc. 1956, 78,2582.   DOI
13 Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763.   DOI
14 Zeynizadeh, B.; Shirini, F. J. Chem. Res. 2003, 335.
15 Zeynizadeh, B.; Shirini, F. Bull. Korean Chem. Soc. 2003, 24, 295and the references cited therein.   DOI   ScienceOn
16 Firouzabadi, H.; Adibi, M.; Ghadami, M. Phosphorus, Sulfur,Silicon Relat. Elem. 1998, 142, 191.   DOI   ScienceOn
17 Firouzabadi, H.; Adibi, M. Synth. Commun. 1996, 26, 2429.   DOI   ScienceOn
18 Firouzabadi, H.; Adibi, M. Phosphorus, Sulfur, Silicon Relat. Elem. 1998, 142, 125.   DOI   ScienceOn
19 Firouzabadi, H.; Afsharifar, G. R. Synth. Commun. 1992, 22, 497.   DOI
20 Firouzabadi, H.; Afsharifar, G. R. Bull. Chem. Soc. Jpn.1995, 68, 2595.   DOI   ScienceOn
21 Kreiser, W. Ann. Chem. 1971, 745, 164.   DOI
22 Pechmann, V. H.;Dahl, F. Chem. Ber. 1890, 23, 2421.   DOI
23 Nutaitis, C. F.; Bernardo, J. E. J. Org. Chem. 1989, 54, 5629.   DOI
24 Guette, J. P.; Spassky, N.; Boucherot, D. Bull. Chem. Soc.Fr. 1972, 4217.
25 Johnson, M. R.; Rickborn, B. J. Org. Chem. 1970, 35, 1041.   DOI
26 Varma, R. S.; Kabalka, G. W. Synth. Commun. 1985, 15, 985.   DOI
27 Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Org. Prep. Proced. Int.1996, 28, 355.   DOI   ScienceOn
28 Cha, J. S.; Kwon, O. O.; Kwon, S. Y. Bull.Korean Chem. Soc. 1995, 16, 1009.
29 Cha, J. S.; Kim, E. J.;Kwon, O. O. Bull. Korean Chem. Soc. 1994, 15, 1033.
30 Kim, S.; Moon, Y. C.; Ahn, K. H. J. Org. Chem. 1982, 47, 3311.   DOI
31 Ravikumar, K. S.; Baskaran, S.; Chandrasekaran, S. J. Org. Chem.1993, 58, 5981.   DOI   ScienceOn
32 Imuta, M.; Ziffer, H. J. Org. Chem. 1978, 43, 3530.   DOI
33 Blomquist, A. T.; Goldstein, A. Org. Synth. Coll. Vol. IV 1963,216.