Diastereoselective Synthesis of Pyranoquinolines on Zirconium‐Containing UiO‐66 Metal‐Organic Frameworks

Rechac, Víctor L.; Cirujano, Francisco G.; Corma, Avelino; Xamena, Françesc X. Llabrés i

doi:10.1002/ejic.201600372

Cited by 46 publications

(23 citation statements)

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“…In another report, UiO-66 and UiO-66-NH 2 were found to be efficient diastereoselective catalysts for the one-pot synthesis of a pyrano[3,2-c]quinoline through an inverse electron-demand aza-Diels-Alder [4 + 2] cycloaddition of an aryl imine (formed in situ by condensation of aniline and benzaldehyde) and 3,4dihydro-2H-pyran (Scheme 4). [35] UiO-66 and UiO-66-NH 2 afforded 83 and 88 % yield of pyrano[3,2-c]quinoline, with 94 and 88 % of diastereomeric excesses for the trans isomer, respectively, at room temperature. Under identical conditions, MIL-101 (Cr), MIL-101(Al)-NH 2 and MIL-101(Fe)-NH 2 showed lower than 5 % yield of the product, suggesting the superior activity of UiO-66, in spite that the structure of MIL-101 materials has open coordination sites on the metal ion that should be absent in ideal UiO-66.…”

Section: Nodes As Lewis Acidsmentioning

confidence: 99%

Engineering UiO‐66 Metal Organic Framework for Heterogeneous Catalysis

et al. 2019

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frameworks (MOFs) are currently attracting considerable attention as heterogeneous catalysts at moderate temperatures, mainly for liquid-phase reactions. Since structural stability is one of the major concerns for the use of MOFs in catalysis, particularly considering that frequently some of the reported MOF materials are very unstable, the interest in this area has been focused on those MOFs exhibiting the highest structural robustness, UiO-66 being among the most widely used. Two introductory sections deal with the synthesis, structure and main properties of UiO-66, including its remarkable thermal (up to 350°C) and chemical (aqueous solution in a wide pH range) stability. The main body of the review summarizes those examples of using UiO-66 in catalysis grouped according to the nature of the active sites, starting with the use of UiO-66 as Lewis acids. In this section, emphasis has been made in the recent strategies to create structural defects in a controlled way that generate Lewis acidity. Other sections cover examples illustrating substituted terephthalate as active sites and the evidence that there is a synergy between acid and basic sites in close proximity that make some of these UiO-66 with substituents at the linker to act as dual acid-base catalysts. Other sections are focused on the use of UiO-66 as hosts of metal nanoparticles, metal oxides and other host, remarking the influence that the nature of UiO-66 and the possible presence of substituents in the framework play on the activity of the incorporated guest. The last section summarizes the current state of the art in the use of UiO-66 in catalysis and provides our views on future developments regarding the application of UiO-66 in industrial processes.

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Section: Nodes As Lewis Acidsmentioning

confidence: 99%

Engineering UiO‐66 Metal Organic Framework for Heterogeneous Catalysis

et al. 2019

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“…[4][5][6][7] In this sense, the Zr-containing terephthalate known as UiO-66 8 and its derivatives have attracted a great deal of attention in recent years. [9][10][11][12][13] These compounds are formed by hexameric [Zr6O4(OH)4] octahedral oxoclusters connected by 12 terephthalate linkers into a face centered cubic packing. The high coordination number of the inorganic building units endows the material with a remarkable thermal, chemical and mechanical stability, 14 which is seldom found in many known MOF compounds.…”

Section: Introductionmentioning

confidence: 99%

Catalytic properties of pristine and defect-engineered Zr-MOF-808 metal organic frameworks

Mautschke

Drache

Senkovska

et al. 2018

Catal. Sci. Technol.

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“…MOFs have been explored for a broad range of catalytic transformations. Reported examples are condensation, ring opening, cycloaddition, N ‐alkylation, isomerization, hydrogenation, oxidation, and carbene reactions. MOF‐based materials are suitable catalysts for the production of certain fine chemicals .…”

Section: Introductionmentioning

confidence: 99%

Catalytic Transfer Hydrogenation of Biomass‐Derived Carbonyls over Hafnium‐Based Metal–Organic Frameworks

2017

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A series of highly crystalline, porous, hafnium-based metal-organic frameworks (Hf-MOFs) have been shown to catalyze the transfer hydrogenation reaction of levulinic ester to produce γ-valerolactone by using isopropanol as a hydrogen donor. The results are compared with their zirconium-based counterparts. The role of the metal center in Hf-MOFs has been identified and reaction parameters optimized. NMR studies using isotopically labeled isopropanol provide evidence that the transfer hydrogenation occurs through a direct intermolecular hydrogen transfer route. The catalyst, Hf-MOF-808, can be recycled several times with only a minor decrease in catalytic activity. The generality of the procedure has been demonstrated by accomplishing the transformation with aldehydes, ketones, and α,β-unsaturated carbonyl compounds. The combination of Hf-MOF-808 with the Brønsted-acidic Al-Beta zeolite gives the four-step one-pot transformation of furfural to γ-valerolactone in good yield of 75 %.

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Diastereoselective Synthesis of Pyranoquinolines on Zirconium‐Containing UiO‐66 Metal‐Organic Frameworks

Cited by 46 publications

References 47 publications

Engineering UiO‐66 Metal Organic Framework for Heterogeneous Catalysis

Engineering UiO‐66 Metal Organic Framework for Heterogeneous Catalysis

Catalytic properties of pristine and defect-engineered Zr-MOF-808 metal organic frameworks

Catalytic Transfer Hydrogenation of Biomass‐Derived Carbonyls over Hafnium‐Based Metal–Organic Frameworks

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