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Chemoselective H/D Exchange Catalyzed by Nickel Nanoparticles Stabilized by N-Heterocyclic Carbene Ligands

Abstract : With this work, we report the synthesis and full characterization of nickel nanoparticles (NPs) stabilized by N-heterocyclic carbene (NHC) ligands, namely 1,3-bis(cyclohexyl)-1,3-dihydro-2H-imidazol-2-ylidene (ICy) and 1,3-bis(2,4,6-trimethylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene (IMes). Although the resulting NPs have the same size, they display different magnetic properties and different reactivities, which result from ligand effects. In the context of H/D exchange on pharmaceutically relevant heterocycles, Ni@NHC shows a high chemoselectivity, avoiding the formation of undesired reduced side-products and enabling a variety of H/D exchange on nitrogen-containing aromatic compounds. Using 2-phenylpyridine as a model substrate, it was observed that deuteration occurred preferably at the α position of the nitrogen atom, which is the most accessible position for the C–H activation. In addition, Ni@IMes NPs are also able to fully deuterate the ortho positions of the phenyl substituents.
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Submitted on : Tuesday, July 21, 2020 - 3:24:07 PM
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Donia Bouzouita, Juan Manuel Asensio, Viktor Pfeifer, Alberto Palazzolo, Pierre Lecante, et al.. Chemoselective H/D Exchange Catalyzed by Nickel Nanoparticles Stabilized by N-Heterocyclic Carbene Ligands. Nanoscale, Royal Society of Chemistry, In press, ⟨10.1039/D0NR04384B⟩. ⟨hal-02903879⟩

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