Efficient Catalysis of the Aerobic Baeyer–Villiger Oxidation over a Bifunctional Catalyst Based on Cobalt Tetraphenylporphyrin Intercalated into Zn<sub>2</sub>Al Hydrotalcite

Zhou, Weiyou; Tian, Peng; Sun, Fei; He, Mingyang; Chen, Zaixin

doi:10.1002/ajoc.201402224

Cited by 26 publications

(11 citation statements)

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“…Horizontal and perpendicular intercalations of metalloporphyrins inside different materials are known [ 42 , 44 , 45 ]. Diagonal orientations have also been reported inside niobite Nb 3 O 8 − [ 19 ].…”

Section: Resultsmentioning

confidence: 99%

“…Ma et al reported that anionic metalloporphyrins were intercalated inside layered double hydroxides in a perpendicular orientation [ 27 ]. Metalloporphyrins intercalated inside layered double hydroxides have been witnessed earlier [ 20 , 28 ]. Tubular halloyasites have also been described for metalloporphyrin intercalation purposes [ 29 ].…”

Section: Introductionmentioning

confidence: 99%

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Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Zyoud

Jondi

Mansour

et al. 2016

Chemistry Central Journal

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BackgroundMetalloporphyrin ions, with planar shape, have been known to intercalate horizontally and diagonally between montmorillonite layers. Perpendicular intercalation inside montmorillonite has not been reported earlier. This work aims at achieving perpendicular intercalation inside montmorillonite in natural clays. Possible intercalation inside other forms of natural clay will also be investigated.MethodsNatural clays were purified and characterized. The naked clay powder was then refluxed with tetra(4-pyridyl)porphyrinatomanganese(III) ion (MnTPyP+) solution in methanol with continuous stirring for different times. Electronic absorption spectra, atomic absorption spectra, Fourier Transform infrared spectra, scanning electron microscopy and X-ray diffraction were all used in clay characterization and in intercalation study.ResultsThe natural clay involved different phases, namely montmorillonite, biotite, kaolinite, illite and traces of quartz. Montmorillonite clay allowed horizontal, diagonal and perpendicular intercalation of the metalloporphyrin ions. Biotite allowed only horizontal intercalation. The mode of intercalation was deduced by monitoring the clay inter-planar distance value change. Intercalation occurred inside both micro- and nano-size clay powders to different extents. The nano-powder (average size ~50 nm) showed uptake values up to 3.8 mg MnTPyP/g solid, whereas the micro-size powder (average size ~316 nm) exhibited lower uptake (2.4 mg MnTPyP/g solid). Non-expandable clay phases did not allow any intercalation. The intercalated MnTPyP+ ions showed promising future supported catalyst applications.ConclusionsDepending on their phase, natural clays hosted metalloporphyrin ions. Montmorillonite can allow all three possible intercalation geometries, horizontal, diagonal and for the first time perpendicular. Biotite allows horizontal intercalation only. Non-expandable clays allow no intercalation.Graphical abstractMetalloporphyrin complexes can be intercalated into montmorillonite in horizontal, perpendicular and diagonal geometriesElectronic supplementary materialThe online version of this article (doi:10.1186/s13065-016-0153-4) contains supplementary material, which is available to authorized users.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Zyoud

Jondi

Mansour

et al. 2016

Chemistry Central Journal

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“…One possible explanation is that acetic acid can be used as a protic acid, which may activate cyclohexanone in the catalytic reaction and accelerate the progress of the reaction. [22] 4 A-MS is a kind of desiccant commonly used in laboratories which with many Lewis acid sites. The conversion of BÀ V oxidation was enhanced because the Lewis acid sites of 4 A-MS activated cyclohexanone and benzaldehyde.…”

Section: Solvent T [°C] Time [H]mentioning

confidence: 99%

“…They found co-catalysts such as SiO 2 , 4 A molecular sieve (MS) could significantly enhance the selectivity of ɛ-caprolactone and reduce the amount of benzaldehyde additive. [20] Iron porphyrin based heterogeneous polymer catalyst FCMP-1 [21] was also effective for BÀ V oxidation and cobalt porphyrin catalyst CoTSPP-Zn 2 Al-LDH [22] may even obtain ɛ-caprolactone as high as 98 % yield. Hybrid porphyrin-heteropolyacid material FPOP also proved active in the BÀ V oxidation of cyclohexanone.…”

Section: Introductionmentioning

confidence: 99%

Aerobic Baeyer‐Villiger Oxidation Catalyzed by Metal Corroles

Wan

Yang

et al. 2022

Eur J Org Chem

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Metal corrole catalyzed Baeyer-Villiger oxidation reaction was successfully achieved for the first time. Among all tested Co, Mn, Fe and Cu complexes of 5, 10, 15-Tris (pentafluorophenyl) corrole, Fe complex [Fe(tpfc)Cl] exhibited the best activity, and the highest yield was observed for six membered cyclic ketones. Preliminary results suggest that Fe(tpfc)Cl may act as an initiator for dehydrogenation of benzaldehyde to generate benzoyl radical, which will form peroxybenzoic acid under molecular oxygen atmosphere. The oxidation of Fe(tpfc)Cl catalyst by peroxybenzoic acid produces high-valent iron-oxo corrole intermediate. The iron-oxo corrole is attacked by cyclohexanone to form a Criegee adduct, which will finally generate ɛcaprolactone product to finish the catalytic cycle. The 4 A-MS additive may accelerate the production of perbenzoic acid and significantly improve the reaction yield.[a] M.

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“…He 153 applied catalyst 49Co (Figure 8) in Baeyer−Villiger oxidation reaction for several cyclic ketones to lactones using benzaldehyde as co-catalyst, at 40 °C, over 7−14 h (Scheme 34). The authors proposed the involvement of peroxybenzoic acid as oxidant, resulting from the in situ oxidation of benzaldehyde with O 2 , yielding the desired lactones in very high yields.…”

Section: Homogeneous Versus Heterogeneous Oxidation Reactions Catalyz...mentioning

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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Efficient Catalysis of the Aerobic Baeyer–Villiger Oxidation over a Bifunctional Catalyst Based on Cobalt Tetraphenylporphyrin Intercalated into Zn₂Al Hydrotalcite

Abstract: Scheme 1. The reaction steps for B-V oxidation with an O 2 /aldehyde system.[a] Dr.

Cited by 26 publications

References 44 publications

Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Aerobic Baeyer‐Villiger Oxidation Catalyzed by Metal Corroles

Metalloporphyrins: Bioinspired Oxidation Catalysts

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Efficient Catalysis of the Aerobic Baeyer–Villiger Oxidation over a Bifunctional Catalyst Based on Cobalt Tetraphenylporphyrin Intercalated into Zn2Al Hydrotalcite

Abstract: Scheme 1. The reaction steps for B-V oxidation with an O 2 /aldehyde system.[a] Dr.

Cited by 26 publications

References 44 publications

Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Modes of tetra(4-pyridyl)porphyrinatomanganese(III) ion intercalation inside natural clays

Aerobic Baeyer‐Villiger Oxidation Catalyzed by Metal Corroles

Metalloporphyrins: Bioinspired Oxidation Catalysts

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Product

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Efficient Catalysis of the Aerobic Baeyer–Villiger Oxidation over a Bifunctional Catalyst Based on Cobalt Tetraphenylporphyrin Intercalated into Zn₂Al Hydrotalcite