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Sustainable Hydrogenation of Nitroarenes to Anilines with Highly Active In-Situ Generated Copper Nanoparticles

preprint
submitted on 28.02.2020 and posted on 02.03.2020 by Fatma Pelin Kinik, Tu Ngugen, Mounir Mensi, Christopher Ireland, Kyriakos Stylianou, Berend Smit

Metal nanoparticles (NPs) are usually stabilized by a capping agent, a surfactant, or a support material, to maintain their integrity. However, these strategies can impact their intrinsic catalytic activity. Here, we demonstrate that the in-situ formation of copper NPs (Cu0NPs) upon the reduction of the earth-abundant Jacquesdietrichite mineral with ammonia borane (NH3BH3, AB) can provide an alternative solution for stability issues. During the formation of Cu0NPs, hydrogen gas is released from AB, and utilized for the reduction of nitroarenes to their corresponding anilines, at room temperature and under ambient pressure. After the nitroarene-to-aniline conversion is completed, regeneration of the mineral occurs upon the exposure of Cu0NPs to air. Thus, the hydrogenation reaction can be performed multiple times without the loss of the Cu0NPs’ activity. As a proof-of-concept, the hydrogenation of drug molecules “flutamide” and “nimesulide” was also performed and isolated their corresponding amino-compounds in high selectivity and yield.

Funding

Swiss National Science Foundation: Ambizione Energy Grant n.PZENP2 166888.

History

Email Address of Submitting Author

berend.smit@epfl.ch

Institution

Ecole Polytechnique Fédérale de Lausanne (EPFL)

Country

Switzerland

ORCID For Submitting Author

0000-0003-4653-8562

Declaration of Conflict of Interest

no conflict of interest

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