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The deoxygenation of amine-N-oxides to amines in the presence of other functional groups is an important transformation in the synthesis of nitrogenous aromatic heterocycles. Many reagents have been employed for the deoxygenation of amine-N-oxides, including agents such as: low-valent titanium, phosphorous and sulphur compounds, tributyltin hydride, Pd/C, tetrathiomolybdate, SmI2, indium/NH4Cl. Recently we reported that Cp2TiCl2/In system could be used for the deoxygenation of various amine-N-oxides. It is expected that FeCl3·6H2O/In system can also be an efficient reagent for the deoxygenation of amine-N-oxides to amines. We have found that various amine-N-oxides 1 on treatment with FeCl3·6H2O/In system are smoothly converted into the corresponding amines 2 in high yields. The new reducing system was generated by the addition of indium powder to a stirred solution of ferric chloride hexahydrate in aqueous methanol under sonication. We herein wish to report a mild and efficient method for the deoxygenation of amine-N-oxides using FeCl3·6H2O/In system. The reactions can be generalized as in eq. 1. Some control experiments revealed that amine-N-

Mild and Efficient Deoxygenation of Amine-N-Oxides with FeCl3·6H2O-Indium System under Ultrasonication

Mild and Efficient Deoxygenation of Amine-N-Oxides with FeCl₃·6H₂O-Indium System under Ultrasonication