Non-Catalyzed Reductions With Formate Salts: Conversion of Nitroaromatic Compounds to the Corresponding Primary Amines
- 1 January 1981
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 11 (11) , 925-930
- https://doi.org/10.1080/00397918108065749
Abstract
One of the more important transformations in aromatic chemistry involves nitration of the ring followed by reduction1 of the nitro group to the corresponding primary amine. Despite its low cost, ease of handling, and known2 property of being a convenient hydrogen donor, formic acid (or formate salts, which are even more active hydride donors2) was not utilized for this reduction until recently when Heck and Cortese reported 3 the palladium-catalyzed reduction of nitroaromatics using triethylammonium formate. Since the latter reagent in N,N-dimethylformamide (DMF) had previously4 been shown to reduce the carbon-carbon double bond in good Michael acceptors without the presence of a metal catalyst, we decided to examine non-catalytic systems involving formic acid5 for effecting reduction of the nitro group.Keywords
This publication has 3 references indexed in Scilit:
- Catalytic reductions with formate ion under phase transfer conditionsTetrahedron Letters, 1981
- Palladium catalyzed reductions of halo- and nitroaromatic compounds with triethylammonium formateThe Journal of Organic Chemistry, 1977
- FORMIC ACID REDUCTION XXV. A SELECTIVE REDUCTION OF CARBON–CARBON DOUBLE BONDS CONJUGATED WITH NITRO, CYANO, OR SULFONYL GROUPChemistry Letters, 1976