Enhanced enantioselective oxidation of olefins catalyzed by Mn-porphyrin immobilized on graphene oxide

Berijani, Kayhaneh; Farokhi, Afsaneh; Hosseini‐Monfared, Hassan; Janiak, Christoph

doi:10.1016/j.tet.2018.03.027

Cited by 36 publications

(22 citation statements)

References 62 publications

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“…Another efficient catalytic system for the enantioselective oxidation of olefins with molecular oxygen and in presence of isobutyraldehyde is constituted by material 170 (Scheme ) …”

Section: Graphene‐ Graphene Oxide‐ and Reduced Graphene Oxide‐based mentioning

confidence: 99%

“…Another efficient catalytic system for the enantioselective oxidation of olefins with molecular oxygen and in presence of isobutyraldehyde is constituted by material 170 (Scheme 66). [179] Catalyst 170 was prepared by the immobilization of a Mn(III)-porphyrin complex with a chiral tartrate counter ion onto GO and was able to catalyze the asymmetric epoxidation of different olefins with low loadings. It was possible to carry out up to five consecutive catalytic runs without any loss of activity and with no leaching of Mn species in the reaction mixture.…”

Section: Organometallic Catalysismentioning

confidence: 99%

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Modified Nanocarbons for Catalysis

2018

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Nanocarbons represent useful scaffolds in the preparation of last generation nanostructured catalysts, and their chemical functionalization through covalent or non‐covalent modification is becoming an important tool for introducing well‐distributed anchoring points and, in the meantime, could be the first step toward the assembling of hybrid nanostructured materials with a hierarchical order. In this Review are reported synthesis and catalytic applications of chemically modified nanocarbons such as fullerene, carbon nanotubes, graphene, nanohorns and nanodiamonds in organocatalytic and metal‐based (metal nanoparticles, organometallic complexes) reactions, covering major chemical reactions encompassing, the oxidation of alcohols, aldehydes, olefins, and silanes, hydrogenation reactions of aldehydes, ketones, and alkenes, dehydrogenative coupling of silanes, C−C coupling reactions, epoxidation of alkenes, CO2 fixation into cyclic carbonates, and asymmetric reactions, among others.

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“…Another efficient catalytic system for the enantioselective oxidation of olefins with molecular oxygen and in presence of isobutyraldehyde is constituted by material 170 (Scheme ) …”

Section: Graphene‐ Graphene Oxide‐ and Reduced Graphene Oxide‐based mentioning

confidence: 99%

Section: Organometallic Catalysismentioning

confidence: 99%

Modified Nanocarbons for Catalysis

2018

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“…In bio‐oxidation mediated by cytochrome P450 enzymes, hydroxylation can be achieved by utilizing NAD(P)H (nicotinamide adenine dinucleotide (phosphate)) as the hydrogen donator for activating molecular oxygen . Therefore, aldehydes as NAD(P)H‐ like hydrogen donator are widely used to activate dioxygen in metalloporphyrins‐catalyzed oxidation system . Other compounds containing active α‐hydrogen are desired to have the efficiency of molecular oxygen activation.…”

Section: Background and Originality Contentmentioning

confidence: 99%

Cyclohexene Promoted Efficient Biomimetic Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Manganese Porphyrin under Mild Conditions

Liu

Xue

et al. 2020

Chin. J. Chem.

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of main observation and conclusion Selective oxidation of alcohols to corresponding carbonyl compounds is one of the most important processes both in academic and application research. As a kind of biomimetic catalyst, metalloporphyrins-catalyzed aerobic oxidation of alcohols with aldehyde as hydrogen donator is gathering much attention. However, using olefins as another kind hydrogen donator for aerobic oxidation of alcohols has not been reported. In this study, a system comprising managenese porphyrin and cyclohexene for biomimetic aerobic oxidation of alcohols to carbonyl compounds was developed. The catalytic system exhibited excellent catalytic performance and selectivity towards the corresponding products for most primary and secondary alcohols under mild conditions. Based on the results obtained from experiments as well as in situ EPR (electron paramagnetic resonance) and UV-vis spectroscopy, the role of cyclohexene was demonstrated. Results and Discussion Catalytic performanceUsing benzyl alcohol as a testing substrate, the reactivity and Chin.

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“…Biomimetic processes are also a convenient alternative for eco-sustainable oxidation processes, since they allow the use of green oxidants, such as H 2 O 2 or O 2 (that afford water as the only by-product), and mild conditions [12][13][14][15][16][17]. This leads to a significant reduction of environmental impact relative to stoichiometric oxidants, such as Cr 2 O 7 2− , MnO 4 − , and dimethyldioxirane (DMD), or milder but expensive oxidants that also generate sub-products, such as m-chloroperoxybenzoic acid (m-CPBA), PhIO, ClO − , HSO 5 − , and IO 4 − .…”

Section: Introductionmentioning

confidence: 99%

Biomimetic Oxidation of Benzofurans with Hydrogen Peroxide Catalyzed by Mn(III) Porphyrins

et al. 2020

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The modelling of metabolic activation of the benzofuran nucleus is important to obtain eco-sustainable degradation methods and to understand the related mechanisms. The present work reports the catalytic oxidation of benzofuran, 2-methylbenzofuran, and 3-methylbenzofuran by hydrogen peroxide, at room temperature, in the presence of different Mn(III) porphyrins as models of cytochrome P450 enzymes. Conversions above 95% were attained for all the substrates. The key step is the formation of epoxides, which undergo different reaction pathways depending on factors, such as the position of the methyl group and the reaction and work-up conditions used.

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Enhanced enantioselective oxidation of olefins catalyzed by Mn-porphyrin immobilized on graphene oxide

Cited by 36 publications

References 62 publications

Modified Nanocarbons for Catalysis

Modified Nanocarbons for Catalysis

Cyclohexene Promoted Efficient Biomimetic Oxidation of Alcohols to Carbonyl Compounds Catalyzed by Manganese Porphyrin under Mild Conditions

Biomimetic Oxidation of Benzofurans with Hydrogen Peroxide Catalyzed by Mn(III) Porphyrins

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