Indium as a reducing agent: Reduction of aromatic nitro groups

Synlett

Volumn , Issue 9, 1998, Pages 1028-

  Moody, Christopher J ^a   Pitts, Michael R ^a  

^a UNIVERSITY OF EXETER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002868261     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1837     Document Type: Article

References (13)

1. For reviews, see: Larock, R. C. Comprehensive Organic Transformations, VCH: New York, 1989, pp. 411-415;
2. Kabalka, G. W.; Varma, R. S. Comprehensive Organic Synthesis; Trost, B. M.; Fleming, I. Eds.; Pergamon Press: Oxford, 1991; Vol. 8; pp. 363-379;
3. Sauvé, 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.
4. Tafesh, A. M.; Weiguny, J. Chem. Rev. 1996, 96, 2035-2052.
5. For recent examples, see: Boothroyd, S. R.; Kerr, M. A. Tetrahedron Lett. 1995, 36, 2411-2414;
6. Suwinski, J.; Wagner, P.; Holt, E. M. Tetrahedron 1996, 52, 9541-9552;
7. Upadhya, T. T.; Katdare, S. P.; Sabde, D. P.; Ramaswamy, V.; Sudalai, A. Chem. Commun. 1997, 1119-1120;
8. Fischer, B.; Sheihet, L. J. Org. Chem. 1998, 63, 393-395;
9. Kumbhar, P. S.; Sanchez-Valente, J.; Figueras, F. Tetrahedron Lett. 1998, 39, 2573-2574.
10. There is a reported example of an apparent nitro group reduction in the presence of indium metal during an attempted addition of the allylindium reagent to 4-nitrobenzaldehyde (Chan, T. H.; Isaac, M. B. Pure Appl. Chem. 1996, 68, 919-924).
11. Moody, C. J.; Pitts, M. R. Synlett 1998, 1029.
12. 4) and concentrated m vacuo. The crude product was purified by flash chromatography to yield the desired product.
13. The product anilines are known compounds whose data agreed closely with literature values.