Alternative method for the reduction of aromatic nitro to amine using TMDS-iron catalyst system

The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac) 3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity...

Full description

Saved in:
Bibliographic Details
Published in:Tetrahedron 2011-03, Vol.67 (10), p.1971-1976
Main Authors: Pehlivan, Leyla, Métay, Estelle, Laval, Stéphane, Dayoub, Wissam, Demonchaux, Patrice, Mignani, Gérard, Lemaire, Marc
Format: Article
Language:English
Subjects:
Amines
Aromatic compounds
Carboxylic acids
Catalysis
Catalysts: preparations and properties
Chemical Sciences
Chemistry
Cyano groups
Esters
Exact sciences and technology
General and physical chemistry
Nitro compounds
Noncondensed benzenic compounds
Organic chemistry
Preparations and properties
Reduction
Tetrahedrons
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The system 1,1,3,3-tetramethyldisiloxane (TMDS)/Fe(acac) 3 is reported here as a new method to obtain amines from aromatic nitro compounds. Amines are synthetized in a straightforward step and are isolated as hydrochloride salts with good to excellent yields. This system has shown a good selectivity toward aryl-chloride, aryl-bromide, ester, carboxylic acid, and cyano groups. The reduction of alkylnitro compounds was unfortunately not possible using this method, only a mixture of mono and dialkylated amine was obtained. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2010.12.070