Selective oxidation of cyclopentene with H2O2 by using H3PW12O40 and TBAB as a phase transfer catalyst

Ya, Luo; Liu, Changjun; Yue, Hairong; Tang, Siyang; Zhu, Yingming; Liang, Bin

doi:10.1016/j.cjche.2018.10.014

Cited by 12 publications

(1 citation statement)

References 38 publications

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“…Due to the characteristics of disproportionation and susceptibility to nucleophilic attack, formyl groups not only endow molecules with more possibilities for reshaping the architecture, such as reconstruction of new C–C or CC bonds via aldol condensation, but also enable organisms to become more diverse in secondary metabolite evolution. − Paired formyl groups are usually generated from the chemical oxidative cleavage of CC bonds, − while those from the cleavage of C–C bonds in epoxides are rare and are mostly catalyzed by transition-metal catalyst tungsten peroxide complexes . SdnB, with a ferriporphyrin center, is the first oxidase that selectively catalyzes such unusual chemical conversion.…”

Section: Results and Discussionmentioning

confidence: 99%

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Chen

Yuan

et al. 2022

J. Am. Chem. Soc.

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Cytochrome P450s are one of the most versatile oxidases that catalyze significant and unique chemical transformations for the construction of complex structural frameworks during natural product biosynthesis. Here, we discovered a set of P450s, including SdnB, SdnH, SdnF, and SdnE, that cooperatively catalyzes the reshaping of the inert cycloaraneosene framework to form a highly oxidized and rearranged sordarinane architecture. Among them, SdnB is confirmed to be the first P450 (or oxidase) that cleaves the C−C bond of the epoxy residue to yield formyl groups in pairs. SdnF selectively oxidizes one generated formyl group to a carboxyl group and accelerates the final Diels−Alder cyclization to furnish the sordarinane architecture. Our work greatly enriches the enzyme functions of the P450 superfamily, supplies the missing skills of the P450 synthetic toolbox, and supports them as biocatalysts in further applications toward the synthesis of new chemical entities.

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Section: Results and Discussionmentioning

confidence: 99%

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Chen

Yuan

et al. 2022

J. Am. Chem. Soc.

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Selective Catalytic Oxidation of Cyclopentene to Glutaraldehyde over Amorphous Nb₂O₅/AC Catalysts

et al. 2022

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Activated carbon supported Nb2O5 catalysts were prepared and applied in the selective catalytic oxidation of cyclopentene to glutaraldehyde with 30 % H2O2 as the oxidant. The 12 %Nb2O5/AC catalysts were characterized by the X‐ray diffraction, transmission electron microscopy and X‐ray photoelectron spectroscopy; the results indicated Nb2O5 particles are of amorphous character. The effects of reaction conditions on the selective catalytic oxidation of cyclopentene were investigated. The conversion of cyclopentene was 84.3 % and the selectivity to glutaraldehyde was up to 75.3 % under the optimized reaction conditions. The radicals trapping experiments combined with the ATR infrared spectra characterization demonstrated that the reactive oxygen species for the catalytic oxidation of cyclopentene to glutaraldehyde over the Nb2O5/AC catalyst are superoxide radical and Nb(OO) species. The adsorbed organic species on the catalyst surface could lead to deactivation of the catalyst.

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Styrene epoxidation catalyzed by polyoxometalate/quaternary ammonium phase transfer catalysts: The effect of cation size and catalyst deactivation mechanism

Xiao

Jiang

Yuan

et al. 2023

Chinese Journal of Chemical Engineering

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Selective oxidation of cyclopentene with H2O2 by using H3PW12O40 and TBAB as a phase transfer catalyst

Cited by 12 publications

References 38 publications

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Selective Catalytic Oxidation of Cyclopentene to Glutaraldehyde over Amorphous Nb₂O₅/AC Catalysts

Styrene epoxidation catalyzed by polyoxometalate/quaternary ammonium phase transfer catalysts: The effect of cation size and catalyst deactivation mechanism

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Selective oxidation of cyclopentene with H2O2 by using H3PW12O40 and TBAB as a phase transfer catalyst

Cited by 12 publications

References 38 publications

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Set of Cytochrome P450s Cooperatively Catalyzes the Synthesis of a Highly Oxidized and Rearranged Diterpene-Class Sordarinane Architecture

Selective Catalytic Oxidation of Cyclopentene to Glutaraldehyde over Amorphous Nb2O5/AC Catalysts

Styrene epoxidation catalyzed by polyoxometalate/quaternary ammonium phase transfer catalysts: The effect of cation size and catalyst deactivation mechanism

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Selective Catalytic Oxidation of Cyclopentene to Glutaraldehyde over Amorphous Nb₂O₅/AC Catalysts