Work

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

Year: 2024

Type: article

Abstract: 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 % tert -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.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.4c10470

Authors: Zining Zhang, Huanchao Gu, Dun-Xu Cao, Zhi Li

Institution: ShanghaiTech University

Language: English

Topic: Coordination Chemistry and Organometallics

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funders: Innovative Research Group Project of the National Natural Science Foundation of China, National Natural Science Foundation of China, ShanghaiTech University