Manganese(III) tetrapyridylporphyrin-chloromethylated MIL-101 hybrid material: A highly active catalyst for oxidation of hydrocarbons

Zadehahmadi, Farnaz; Tangestaninejad, Shahram; Moghadam, Majid; Mirkhani, Valiollah; Mohammadpoor‐Baltork, Iraj; Khosropour, Ahmad Reza; Kardanpour, Reihaneh

doi:10.1016/j.apcata.2014.03.003

Cited by 49 publications

(22 citation statements)

References 62 publications

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“…[31][32][33] Metal cations or functional groups on the organic linkers in the framework can be used to catalyze organic transformations, thus maximizing the opportunity for high dispersion and high loading of catalytically active sites. [32,[34][35][36][37][38][39][40] During the last few years, both carbon-carbon [41][42][43][44][45][46][47][48][49][50][51] and carbon-heteroatom-forming organic reactions [52][53][54][55][56][57][58][59][60] using MOF-based catalysts have been reported in the literature. [31-33, 61, 62] Among many popularMOFs, copper-based frameworks have been investigated as catalysts for av ariety of organic transformationso wing to their unsaturated open copperm etal sites.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2‐Dicarbonyl‐3‐enes by Hydroacylation of 1‐Alkynes with Glyoxal Derivatives Using Metal–Organic Framework Cu/MOF‐74 as Heterogeneous Catalyst

Nguyen

Dang

et al. 2016

ChemPlusChem

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A crystalline copper‐based metal–organic framework Cu/MOF‐74 was synthesized, and used as an efficient heterogeneous catalyst for the synthesis of 1,2‐dicarbonyl‐3‐enes by means of the hydroacylation of 1‐alkynes with glyoxal derivatives in the presence of a base. Cu/MOF‐74 was found to be more catalytically active for the synthesis of 1,2‐dicarbonyl‐3‐enes than other MOFs including Cu2(BDC)2(DABCO), Cu3(BTC)2, Cu(BDC), Cu2(NDC)2(DABCO), Cu4I4(DABCO)2, Ni‐MOF‐74, Zn‐MOF‐74, Fe3O(BDC)3, In(OH)(BDC), and Zr6O4(OH)4(BDC)6. Cu/MOF‐74 also exhibited better performance than other homogeneous copper catalysts, including Cu(OAc)2, Cu(NO3)2, CuI, CuBr, CuCl, CuCl2, and CuBr2. The Cu/MOF catalyst was able to be recovered and reused several times without a significant degradation in catalytic activity. To the best of our knowledge, the formation of 1,2‐dicarbonyl‐3‐enes has not previously been carried out under heterogeneous catalysis conditions.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 1,2‐Dicarbonyl‐3‐enes by Hydroacylation of 1‐Alkynes with Glyoxal Derivatives Using Metal–Organic Framework Cu/MOF‐74 as Heterogeneous Catalyst

Nguyen

Dang

et al. 2016

ChemPlusChem

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“…The intact structure of the POM in the composite material was also confirmed using FT‐IR vibrational spectroscopy. As shown in Figure (b), the FT‐IR spectrum of Co‐POM@MIL‐101 is the sum of the characteristic bands of the free components: Co‐POM (Figure a) with characteristic peaks in the region 700–1200 cm −1 assigned to W═O, WOW and CoO bonds and MIL‐101 (Figure c) with characteristic vibrational bands of (OCO) groups of the framework around 1550 and 1400 cm −1 and of C═O vibrations at 1708 and 1658 cm −1 …”

Section: Resultsmentioning

confidence: 99%

Dodecatungstocobaltate heteropolyanion encapsulation into MIL‐101(Cr) metal–organic framework scaffold provides a highly efficient heterogeneous catalyst for methanolysis of epoxides

Marandi

Tangestaninejad

Mirkhani

et al. 2017

Applied Organom Chemis

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A heterogeneous catalyst was synthesized by encapsulation of a Keggin‐type heteropolytungstate, potassium dodecatungstocobaltate trihydrate, K5[CoW12O40]·(Co‐POM), into chromium(III) terephthalate (MIL‐101). Encapsulation was achieved via a ‘build bottle around ship’ strategy in aqueous media, following a hydrothermal method. The structure of the resulting crystalline solid was characterized using X‐ray diffraction, correlated with Fourier transform infrared and UV–visible spectroscopy. The metal content was analysed using optical emission spectroscopy. Transmission electron microscopy was used to measure particle size and N2 adsorption in a Brunauer–Emmett–Teller instrument to characterize the specific surface area. The catalytic activity was investigated using methanolysis of epoxides under mild conditions as a test reaction. The turnover frequency of the heterogeneous Co‐POM@MIL‐101 catalyst was more than 20 times higher than that of the homogeneous Co‐POM catalyst. The Co‐POM@MIL‐101 catalyst was reused several times with negligible leaching of Co‐POM and with no considerable loss of its initial efficiency. The simplicity of preparation, extraordinary stability and high reactivity make Co‐POM@MIL‐101 an exceptional catalytic matrix that is easily separable from reaction media.

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“…It was then washed with boiling THF for 3 hr. The resulting MIL‐101(Cr)‐CH 2 Cl product was dried in a furnace at 100°C for 12 hr as a light green solid (0.7 g) …”

Section: Methodsmentioning

confidence: 99%

Immobilized Pd on a NHC functionalized metal–organic framework MIL‐101(Cr): an efficient heterogeneous catalyst in Suzuki−Miyaura coupling reaction in water

Niknam

Panahi

Khalafi‐Nezhad

2020

Applied Organom Chemis

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A novel Pd−NHC functionalized metal–organic framework (MOF) based on MIL‐101(Cr) was synthesized and used as an efficient heterogeneous catalyst in the C‐C bond formation reactions. Using this heterogeneous Pd catalyst system, the Suzuki−Miyaura coupling reaction was accomplished well in water, and coupling products were obtained in good to excellent yields in short reaction time. The Pd−NHC−MIL‐101(Cr) was characterized using some different techniques, including Fourier transform‐infrared, X‐ray diffraction, scanning electron microscopy, energy‐dispersive X‐ray spectroscopy, transmission electron microscopy (TEM), X‐ray photoelectron spectroscopy, inductively coupled plasma and elemental analysis. The microscopic techniques showed the discrete octahedron structure of MIL‐101(Cr), which is also stable after chemical modification process to prepare the catalyst system. The TEM images of the catalyst showed the existence of palladium nanoparticles immobilized in the structure of the catalyst, while no reducing agent was used. It seems that the NHC groups and imidazolium moieties in the structure of the MOF can reduce Pd (II) to Pd (0) species. This modified MOF substrate can also prevent aggregation of Pd nanoparticles, resulting in high stability of them in organic transformation. The Pd−NHC−MIL‐101(Cr) catalyst system could be simply extracted from the reaction mixture, providing an efficient synthetic method for the synthesis of biaryls derivatives using the aforementioned coupling reaction. The Pd−NHC−MIL‐101(Cr) catalyst could be recycled in this organic reaction with almost consistent catalytic efficiency.

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Manganese(III) tetrapyridylporphyrin-chloromethylated MIL-101 hybrid material: A highly active catalyst for oxidation of hydrocarbons

Cited by 49 publications

References 62 publications

Synthesis of 1,2‐Dicarbonyl‐3‐enes by Hydroacylation of 1‐Alkynes with Glyoxal Derivatives Using Metal–Organic Framework Cu/MOF‐74 as Heterogeneous Catalyst

Synthesis of 1,2‐Dicarbonyl‐3‐enes by Hydroacylation of 1‐Alkynes with Glyoxal Derivatives Using Metal–Organic Framework Cu/MOF‐74 as Heterogeneous Catalyst

Dodecatungstocobaltate heteropolyanion encapsulation into MIL‐101(Cr) metal–organic framework scaffold provides a highly efficient heterogeneous catalyst for methanolysis of epoxides

Immobilized Pd on a NHC functionalized metal–organic framework MIL‐101(Cr): an efficient heterogeneous catalyst in Suzuki−Miyaura coupling reaction in water

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