Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

Teramura, Kentaro; Tsuneoka, Hideo; Ogura, Kentaro; Sugimoto, Takashi; Shishido, Toetsu; Tanaka, Tsunehiro

doi:10.1002/cctc.201402131

Cited by 9 publications

(2 citation statements)

References 42 publications

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“…The catalyst was selective for 1,2-epoxycyclohexane during photocatalytic aerobic cyclohexene epoxidation. The authors concluded that [Fe(TPFPP)Cl]/Mg/Al-LDH was an effective photocatalyst for the oxidation of various alkenes [58].…”

Section: Ldh and Lhs As Support For Metalloporphyrin Immobilizationmentioning

confidence: 99%

Recent Advances in Solid Catalysts Obtained by Metalloporphyrins Immobilization on Layered Anionic Exchangers: A Short Review and Some New Catalytic Results

et al. 2016

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Layered materials are a very interesting class of compounds obtained by stacking of two-dimensional layers along the basal axis. A remarkable property of these materials is their capacity to interact with a variety of chemical species, irrespective of their charge (neutral, cationic or anionic). These species can be grafted onto the surface of the layered materials or intercalated between the layers, to expand or contract the interlayer distance. Metalloporphyrins, which are typically soluble oxidation catalysts, are examples of molecules that can interact with layered materials. This work presents a short review of the studies involving metalloporphyrin immobilization on two different anionic exchangers, Layered Double Hydroxides (LDHs) and Layered Hydroxide Salts (LHSs), published over the past year. After immobilization of anionic porphyrins, the resulting solids behave as reusable catalysts for heterogeneous oxidation processes. Although a large number of publications involving metalloporphyrin immobilization on LDHs exist, only a few papers have dealt with LHSs as supports, so metalloporphyrins immobilized on LHSs represent a new and promising research field. This work also describes new results on an anionic manganese porphyrin (MnP) immobilized on Mg/Al-LDH solids with different nominal Mg/Al molar ratios (2:1, 3:1 and 4:1) and intercalated with different anions (CO 3 2´o r NO 3´) . The influence of the support composition on the MnP immobilization rates and the catalytic performance of the resulting solid in cyclooctene oxidation reactions will be reported.

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Section: Ldh and Lhs As Support For Metalloporphyrin Immobilizationmentioning

confidence: 99%

Recent Advances in Solid Catalysts Obtained by Metalloporphyrins Immobilization on Layered Anionic Exchangers: A Short Review and Some New Catalytic Results

et al. 2016

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“…Using molecular oxygen as an oxidant is a longstanding strategic subject, − and significant achievements in aerobic epoxidation have been made. − Nevertheless, most reports − have used metallic compounds/additives or metallic catalysts/coreductants (such as Et 2 Zn/amino alcohol, Co(II)TPP-OCH 3 /isobutyraldehyde, and Mn(TPP)OAc/isobutyraldehyde) (Scheme a), which always lead to metal residue and poor atom economy. Only a limited number of reports , related to the catalytic epoxidation of α,β-unsaturated ketones with molecular oxygen as the oxidant in the absence of metallic compounds have been reported.…”

Section: Introductionmentioning

confidence: 99%

Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Zhou

Meng

et al. 2018

J. Org. Chem.

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An aerobic photoepoxidation of α,β-unsaturated ketones driven by visible light in the presence of tetramethylguanidine (3b), tetraphenylporphine (H 2 TPP), and molecular oxygen under mild conditions was revealed. The corresponding α,β-epoxy ketones were obtained in yields of up to 94% in 96 h. The reaction time was shortened to 4.6 h by flow synthesis. The mechanism related to singlet oxygen was supported by experiments and density functional theory (DFT) calculations.

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Oxiranes and Oxirenes: Fused-Ring Derivatives

Gras

Sadek

2022

Comprehensive Heterocyclic Chemistry IV

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Photoactivation of Molecular Oxygen by an Iron(III) Porphyrin with a Magnesium Aluminum Layered Double Hydroxide for the Aerobic Epoxidation of Cyclohexene

Cited by 9 publications

References 42 publications

Recent Advances in Solid Catalysts Obtained by Metalloporphyrins Immobilization on Layered Anionic Exchangers: A Short Review and Some New Catalytic Results

Recent Advances in Solid Catalysts Obtained by Metalloporphyrins Immobilization on Layered Anionic Exchangers: A Short Review and Some New Catalytic Results

Visible Light-Induced Aerobic Epoxidation of α,β-Unsaturated Ketones Mediated by Amidines

Oxiranes and Oxirenes: Fused-Ring Derivatives

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