Silver-Mediated Deuterium Labelling of Quinones and Related Compounds by Hydrogen Isotope Exchange With D₂O

We report a silver-catalyzed hydrogen isotope exchange reaction that enables direct deuteration of quinones and related scaffolds, using readily available D₂O as an isotopic source. The homogeneous Ag₂SO₄ system provides high isotopic enrichment, up to 99%, with excellent regioselectivity across diverse frameworks, including substituted para-naphthoquinones, anthraquinones, coumarins, quinolinones, and chromones. We also developed a heterogeneous version of the same reaction by supporting silver nanoparticles on carbon nanotubes. The nanohybrid catalyst maintains high performance and allows for easy removal of the catalyst from the final product through filtration. The dual homogeneous/heterogeneous approaches pioneer quinone hydrogen isotope exchange, providing practical and straightforward access to isotopologues.