Rapid Access to Isoprenoid\nQuinones through X@RONa-Catalyzed\nRedox Chain Reaction

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