Issue 91, 2016, Issue in Progress

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

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

Supplementary files

Article information

Article type
Paper
Submitted
19 Aug 2016
Accepted
01 Sep 2016
First published
02 Sep 2016

RSC Adv., 2016,6, 88366-88372

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, E. A. Artiukha, G. A. Bukhtiyarova, S. Y. Zaytsev, P. E. Plyusnin, Y. V. Shubin and V. I. Bukhtiyarov, RSC Adv., 2016, 6, 88366 DOI: 10.1039/C6RA20904A

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