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Updated: Jun 11, 2025
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Rapid Access to Isoprenoid Quinones through X@RONa-Catalyzed Redox Chain Reaction
Zining Zhang1, Huanchao Gu1, Dun-Xu Cao1
1School of Physical Science and Technology, ShanghaiTech University, 393 Middle Huaxia Road, Pudong District, Shanghai 201210, China.
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.
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