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Nanomaterials 2016, 6(3), 54; doi:10.3390/nano6030054

Reduction of Nitroarenes into Aryl Amines and N-Aryl hydroxylamines via Activation of NaBH4 and Ammonia-Borane Complexes by Ag/TiO2 Catalyst

1
Department of Chemistry, Aristotle University of Thessaloniki, University Campus, Thessaloniki 54124, Greece
2
Department of Materials Science and Technology, University of Crete, Vassilika Vouton, Heraklion 71003, Greece
*
Author to whom correspondence should be addressed.
Academic Editors: Hermenegildo García and Sergio Navalón
Received: 10 February 2016 / Revised: 9 March 2016 / Accepted: 10 March 2016 / Published: 22 March 2016
(This article belongs to the Special Issue Nanoparticles for Catalysis)
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Abstract

In this study, we report the fabrication of mesoporous assemblies of silver and TiO2 nanoparticles (Ag/MTA) and demonstrate their catalytic efficiency for the selective reduction of nitroarenes. The Ag/TiO2 assemblies, which show large surface areas (119–128 m2·g−1) and narrow-sized mesopores (ca. 7.1–7.4 nm), perform as highly active catalysts for the reduction of nitroarenes, giving the corresponding aryl amines and N-aryl hydroxylamines with NaBH4 and ammonia-borane (NH3BH3), respectively, in moderate to high yields, even in large scale reactions (up to 5 mmol). Kinetic studies indicate that nitroarenes substituted with electron-withdrawing groups reduced faster than those with electron-donating groups. The measured positive ρ values from the formal Hammett-type kinetic analysis of X-substituted nitroarenes are consistent with the proposed mechanism that include the formation of possible [Ag]-H hybrid species, which are responsible for the reduction process. Because of the high observed chemo selectivities and the clean reaction processes, the present catalytic systems, i.e., Ag/MTA-NaBH4 and Ag/MTA-NH3BH3, show promise for the efficient synthesis of aryl amines and N-aryl hydroxylamines at industrial levels. View Full-Text
Keywords: silver nanoparticles; nitroarenes; aryl amines; N-aryl hydroxylamines; titania; heterogeneous catalysis; selective reduction silver nanoparticles; nitroarenes; aryl amines; N-aryl hydroxylamines; titania; heterogeneous catalysis; selective reduction
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Andreou, D.; Iordanidou, D.; Tamiolakis, I.; Armatas, G.S.; Lykakis, I.N. Reduction of Nitroarenes into Aryl Amines and N-Aryl hydroxylamines via Activation of NaBH4 and Ammonia-Borane Complexes by Ag/TiO2 Catalyst. Nanomaterials 2016, 6, 54.

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