Chemoselective reduction of nitroaromatics to anilines using decaborane in methanol

Tetrahedron Letters

Volumn 41, Issue 2, 2000, Pages 175-177

  Bae, Jong Woo ^a   Cho, Young Jin ^a   Lee, Seung Hwan ^a   Yoon, Cheol Min ^a  

^a Korea University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; AROMATIC NITRO COMPOUND; METHANOL;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; REACTION ANALYSIS; REDUCTION;

EID: 0001323617     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02048-1     Document Type: Article

References (11)

1. Mestoni, G.; Camus, A.; Zassinovich, G. In Aspects of Homogeneous Catalysis; Ugo, R., Ed.; Reidel: Dordrecht, 1981; Vol. 4, 71-80.
2. Sauve, G.; Rao, V. S. Comprehensive Organic Functional Group Transformations; Katritzky, A. R.; Meth-Cohn, O.; Rees, C. W. Eds.; Pergamon Press: Oxford, 1995; Vol. 2; pp. 737-817.
3. Moody, C. J.; Pitts, M. R. Synlett. 1998, 1028.
4. Banik, B. K.; Mukhopadhyay, C.; Venkatraman, M. S.; Becker, F. F. Tetrahedron Lett. 1998, 39, 7243.
5. Boothroyd, S. R.; Kerr, M. A. Tetrahedron Lett. 1995, 36, 2411.
6. Kumbhar, P. S.; Sanchez-Valente, J.; Figueras, F. Tetrahedron Lett. 1998, 39, 2573.
7. Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393.
8. Suwinski, J.; Wagner, P.; Holt, E. M. Tetrahedron. 1996, 52, 9541.
9. A representative run (entry 3) is as follows: To a solution of benzyl 4-nitrobenzoate (50 mg, 0.276 mmol) in methanol (5 ml) was added decaborane (10 mg), two drops of acetic acid and 10% Pd/C (15 mg). The resulting solution was stirred at reflux under nitrogen for 0.5 h. The reaction was followed by TLC using a solution of ethyl acetate and n-hexane (1:2). The mixture was concentrated under reduced pressure, chromatographed on a short pad of silica gel using a solution of ethyl acetate and n-hexane (1:4) to give benzyl 4-aminobenzoate as a pale yellow solid.
10. f value of the adduct was higher than that of the corresponding amine according to TLC when a mixture of ethyl acetate and n-hexane (1:4) was used as the developing solvent.
11. The starting nitroaromatics remained even after stirring for 2 days or longer. After stirring for 2 days, all of the decaborane was consumed.