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Synthesis of unsaturated secondary amines by direct reductive amination of aliphatic aldehydes with nitroarenes over Au/Al2O3 catalyst in continuous flow mode†
A. L. Nuzhdin,G. A. Bukhtiyarova,S. Yu Zaytsev
RSC Advances Pub Date : 09/02/2016 00:00:00 , DOI:10.1039/C6RA20904A
Abstract

A series of unsaturated secondary amines was successfully synthesized by direct reductive amination of aliphatic aldehydes with nitroarenes over a 2.5% Au/Al2O3 catalyst in a continuous flow reactor using molecular hydrogen as a reducing agent. In most cases, the targeted secondary amines were obtained in good to excellent yields. Interestingly, the hydrogenation of C[double bond, length as m-dash]C group is practically absent in both initial aldehydes and secondary amines under the reaction conditions. It was found that the introduction of electron-donating substituents in the para- and meta-position of nitrobenzenes increased the yield of secondary amine, while in the case of nitrobenzenes with electron-withdrawing substituents or electron-donating substituents in the ortho-position a decrease in the yield of the target product was observed.

Graphical abstract: Synthesis of unsaturated secondary amines by direct reductive amination of aliphatic aldehydes with nitroarenes over Au/Al2O3 catalyst in continuous flow mode
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