Biomimetic Epoxidation of Olefins Catalyzed by Metalloporphyrins with Molecular Oxygen

Ji, Hongbing; Zhou, Xiantai

doi:10.5772/14046

Cited by 4 publications

(3 citation statements)

References 80 publications

(88 reference statements)

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“…Secondly, the acylperoxy radical reacts with another isobutyraldehyde molecule as a carrier to give peroxyacid (Scheme d), then generating another acyl radical (pathway II). Formation of epoxide is granted by active high valent metal oxo intermediates, which are formed by the reaction of the peroxyacid with the metalloporphyrin …”

Section: Resultsmentioning

confidence: 99%

“…Formation of epoxide is granted by active high valent metal oxo intermediates, which are formed by the reaction of the peroxyacid with the metalloporphyrin. [61] 4 | CONCLUSIONS In conclusion, reusable solid biomimetic catalysts were prepared through covalently immobilizing of Fe (TCPP) Cl and Mn (TCPP)OAc to the modified MWCNTs within the ester bond. The catalytic activities of these catalysts were compared in the aerobic oxidation of various alkanes and alkenes.…”

Section: The Proposed Mechanismmentioning

confidence: 96%

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A practical innovative method for highly selective oxidation of alkenes and alkanes using Fe (III) and Mn (III) porphyrins supported onto multi‐wall carbon nanotubes as reusable heterogeneous catalysts

Rayati

Nafarieh

2019

Applied Organom Chemis

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Functionalized multi‐walled carbon nanotubes were used for covalent immobilization of meso‐tetrakis(4‐carboxyphenyl) porphyrinatoiron (III) chloride [Fe (TCPP)Cl] and meso‐tetrakis(4‐carboxyphenyl) porphyrinatomanganese (III) acetate [Mn (TCPP)OAc]. The full characterization of the hybrid porphyrinic nanomaterials, by Fourier transform‐infrared and UV–Vis spectroscopy, transmission electron microscopy, thermogravimetry and flame atomic absorption spectrometry is described. The oxidation of alkenes and alkanes with molecular oxygen as green oxidant in the presence of Mn‐ and Fe‐catalysts has been studied in a comparative manner. The Fe‐catalyst was shown to have higher catalytic activity compared with the Mn‐catalyst. In addition, both separable solid catalysts can be recovered and reused at least 10 times along with good yields.

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Section: Resultsmentioning

confidence: 99%

Section: The Proposed Mechanismmentioning

confidence: 96%

A practical innovative method for highly selective oxidation of alkenes and alkanes using Fe (III) and Mn (III) porphyrins supported onto multi‐wall carbon nanotubes as reusable heterogeneous catalysts

Rayati

Nafarieh

2019

Applied Organom Chemis

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“…Of the several available oxygen donors, which include sodium hypochlorite (NaOCl), iodosylbenzene (PhIO), alkyl peroxides (ROOH), hydrogen peroxide (H 2 O 2 ), and oxygen (O 2 ), the latter is, undoubtedly, the most attractive, given its ubiquity and convenient handling, as well as its ability to mimic the cytochrome P-450 mechanism of action. , The utilization of O 2 , whose ground state is a low-reactivity triplet, in biomimetic catalytic systems requires the presence of an electron donor to initiate the catalytic cycle. This can be the porphyrin itself, as described by Groves in his seminal work using ruthenium porphyrins, aldehydes in systems following Mukaiyama-type mechanisms, and others. − It is generally accepted that the mono-oxygenase-mediated biological oxygenation mechanism (Figure ) involves two-electron reduction, with those electrons provided by the NADPH reductase. The first electron is used to reduce the Fe(III) ferric species to an Fe(II) ferrous species.…”

Section: Introductionmentioning

confidence: 99%

Metalloporphyrins: Bioinspired Oxidation Catalysts

2018

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The utilization of metalloporphyrins as bioinspired oxidation catalysts is an evolving topic of research. By understanding the cytochrome P-450 mechanism of action, chemists have been able to successfully mimic several types of oxidation reactions using metalloporphyrins as catalysts. At first, homogeneous systems presented the most amenable strategy for oxidizing a vast array of substrates; however, current environmental concerns have directed research in this field to the design, synthesis, and application of heterogeneous catalysts, as well as avoiding the use of highly pollutant co-oxidants and/or co-catalysts. Herein, we review the past decade (from 2008) concerning the use of solely molecular oxygen as an environmentally benign oxidant source, in oxidation reactions catalyzed by bioinspired metalloporphyrin analogues. We did not intend to create a comprehensive review; instead we highlight the most important and illustrative examples for this period. We emphasize the application of such catalysts on the oxidation reactions of many relevant substrates using homogeneous and heterogeneous metalloporphyrin-based catalysts, mostly using inorganic supports for more accessible re-utilization protocols.

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Influence of substituents in meso-aryl groups of iron μ-oxo porphyrins on their catalytic activity in the oxidation of cycloalkanes

et al. 2016

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Biomimetic Epoxidation of Olefins Catalyzed by Metalloporphyrins with Molecular Oxygen

Cited by 4 publications

References 80 publications

A practical innovative method for highly selective oxidation of alkenes and alkanes using Fe (III) and Mn (III) porphyrins supported onto multi‐wall carbon nanotubes as reusable heterogeneous catalysts

A practical innovative method for highly selective oxidation of alkenes and alkanes using Fe (III) and Mn (III) porphyrins supported onto multi‐wall carbon nanotubes as reusable heterogeneous catalysts

Metalloporphyrins: Bioinspired Oxidation Catalysts

Influence of substituents in meso-aryl groups of iron μ-oxo porphyrins on their catalytic activity in the oxidation of cycloalkanes

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