Rapid Access to Isoprenoid Quinones through X@RONa-Catalyzed Redox Chain Reaction

Dodecameric sodium alkoxide clusters encaging a halide anion (X@RONa) were shown to be C-C bond formation catalysts in the redox chain reaction of quinones. With up to 30 mol % <i>tert</i>-decanol as the catalyst and stoichiometric base NaH, a great number of chemically sensitive isoprenoid quinones, including health-relevant Coenzyme Q and Vitamin K family compounds, were easily made in one step from their parent quinones and polyprenyl halide. The X@RONa clusters and possible cluster-derived intermediates were studied by characterization techniques, control experiments, and theory. The X@RONa clusters likely facilitated the C-alkylation step by preventing O-alkylation, promoting dissociation of halide from the alkyl chain, and transporting hydride into the nonpolar solvent.