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Catalytic behavior of copper–amine complex supported on mesoporous silica SBA-15 toward mono-Aza-Michael addition: role of amine groups

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Abstract

This work concerns the preparation and modification of mesoporous silica SBA-15 with different amine-copper complexes in order to study their impact on the catalytic behavior via Aza Michael addition. Firstly, SBA-15 was prepared hydrothermally, then functionalized by mono-, di- and tri-amine, and in the second step, copper (II) was anchored. The catalytic activity of these solids was evaluated at room temperature under liquid-phase conditions. Effects of catalyst nature, catalyst mass, reaction time and the starting reagents nature were investigated. Cu@SBA-15 (non-aminated) was shown to be efficient in the Aza Michael addition, but after its second re-use, a progressive decrease in the product yield was obtained due to copper leaching. The catalytic behavior of all prepared catalysts showed a selective reaction via the mono-Aza-Michael addition. Amongst all the catalysts, the one containing the monoamine-copper complex led to the highest yield. This catalyst was used in four consecutive cycles without significant loss of activity, which confirms its stability.

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Authors and Affiliations

  1. Laboratoire de Chimie des Matériaux L.C.M, Université Oran1 Ahmed Ben Bella, El-Mnaouer, BP 1524, 31000, Oran, Algeria

    Aboubakr Hakiki, Bouhadjar Boukoussa, Abdelkader Bengueddach & Rachida Hamacha

  2. Laboratoire de Chimie Fine L.C.F, Université Oran 1 Ahmed Ben Bella, El-Mnaouer, BP 1524, 31000, Oran, Algeria

    Riad Mustpha Kerbadou, Hadjira Habib Zahmani & Salih Hacini

  3. Département de Génie des Matériaux, Faculté de Chimie, Université des Sciences et de la Technologie Mohamed Boudiaf, El-Mnaouer, BP 1505, Oran, Algeria

    Bouhadjar Boukoussa

  4. Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Laboratoire de Réactivité de Surface (LRS, UMR 7197), 4 Place Jussieu (case courrier 197), 75005, Paris, France

    Franck Launay

  5. Sorbonne Université, Faculté des Sciences et Ingénierie, CNRS, Laboratoire Interfaces et Systèmes Electrochimiques (LISE, UMR 8235), 4 place Jussieu (case courrier 133), 75005, Paris, France

    Alain Pailleret & Françoise Pillier

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  1. Aboubakr Hakiki
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  9. Abdelkader Bengueddach
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Correspondence to Bouhadjar Boukoussa.

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Hakiki, A., Kerbadou, R.M., Boukoussa, B. et al. Catalytic behavior of copper–amine complex supported on mesoporous silica SBA-15 toward mono-Aza-Michael addition: role of amine groups. J Inorg Organomet Polym 29, 1773–1784 (2019). https://doi.org/10.1007/s10904-019-01139-7

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