Journal
NANOSCALE
Volume 12, Issue 29, Pages 15736-15742Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0nr04384b
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Funding
- ERC [MONACAT 2015-694159]
- European Union [N675071]
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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 alpha 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 theorthopositions of the phenyl substituents.
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