Biomimetic conversion of α-pinene with H2O2 to sobrerol over V2O5: Dihydroxylation by a peroxo vanadium peracid vectoring gentle synergistic oxidation

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. Th...

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Bibliographic Details
Published in:Catalysis communications 2020-07, Vol.142, p.106041, Article 106041
Main Authors: Liu, Qiang, Huang, Geng, He, Huiting, Xu, Qiong, Li, Hui, Liu, Jian, Liu, Xianxiang, Mao, Liqiu, Kirk, Steven Robert, Su, Shengpei, Yin, Dulin
Format: Article
Language:English
Subjects:
Dihydroxylation
Hydrogen peroxide
Sobrerol
V2O5
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Summary: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. [Display omitted] •A gentle preparation of sobrerol from α-pinene catalyzed by V2O5-H2O2.•Peroxo vanadium acid exhibited bifunctional catalytic capabilities in the system.•This route is no peroxyacetic acid and more efficient for practical applications.
ISSN:1566-7367
1873-3905
DOI:10.1016/j.catcom.2020.106041