Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation
Qiang Liu, Geng Huang, Huiting He, Qiong Xu, Hui Li, Jian Liu, Xianxiang Liu, Liqiu Mao, Steven R. Kirk, Shengpei Su, Dulin Yin
Abstract
In this communication, we report the gentle preparation of sobrerol from dihydroxylation of α-pinene synergistically catalyzed by V2O5-H2O2 under benign conditions. It was proposed that a “peroxo vanadium acid”, VVO(OH)(OOH), was formed by HOO− insertion and proton transfer between V2O5 and H2O2. Theoretical DFT calculations that using the dimer‑vanadium peracid as a model of the catalytically active species revealed that peroxo vanadium acid exhibited bifunctional catalytic capabilities resembling epoxidation of α-pinene by peracetic acid and then open-ring hydration with an acetic media.
Topics & Concepts
VanadiumPeracetic acidDihydroxylationCatalysisChemistryDimerBifunctionalAcetic acidOrganic chemistryCombinatorial chemistryEnantioselective synthesisHydrogen peroxideVanadium and Halogenation ChemistryPolyoxometalates: Synthesis and ApplicationsOxidative Organic Chemistry Reactions