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Highly chemo- and regioselective reduction of aromatic nitro compounds using the system silane/oxo-rhenium complexes.

Authors :
de Noronha RG
Romão CC
Fernandes AC
Source :
The Journal of organic chemistry [J Org Chem] 2009 Sep 18; Vol. 74 (18), pp. 6960-4.
Publication Year :
2009

Abstract

The reduction of aromatic nitro compounds to the corresponding amines with silanes catalyzed by high valent oxo-rhenium complexes is reported. The catalytic systems PhMe(2)SiH/ReIO(2)(PPh(3))(2) (5 mol %) and PhMe(2)SiH/ReOCl(3)(PPh(3))(2) (5 mol %) reduced efficiently a series of aromatic nitro compounds in the presence of a wide range of functional groups such as ester, halo, amide, sulfone, lactone, and benzyl. This methodology also allowed the regioselective reduction of dinitrobenzenes to the corresponding nitroanilines and the reduction of an aromatic nitro group in presence of an aliphatic nitro group.

Details

Language :
English
ISSN :
1520-6904
Volume :
74
Issue :
18
Database :
MEDLINE
Journal :
The Journal of organic chemistry
Publication Type :
Academic Journal
Accession number :
19685891
Full Text :
https://doi.org/10.1021/jo9008657