Synergic effect of copper-based metal–organic frameworks for highly efficient C–H activation of amidines

Xu, Fen; Kang, Wei-Fen; Wang, Xiaoning; Kou, Hao-Dong; Jin, Zhen; Liu, Chun‐Sen

doi:10.1039/c7ra10682c

Cited by 17 publications

(19 citation statements)

References 55 publications

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“…Their advantages are related to tunable compositions, high porosity and readiness of functionalization with organic ligands for some chemical and physical processing. These compounds can be applied across various areas such as clean energy, gas storage media for such gases as hydrogen and methane, drug delivery, catalysis, separation and chemical sensing [16,17]. More than 90% volume of the crystalline MOF material is porosity, thereby surface areas of these materials are very high (close to 6000 m 2 /g) [16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

et al. 2020

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Magnetic particles were prepared by a hydrothermal method and then successively covered by Metal-Organic-Frameworks MIL-101-NH 2 with a high surface area. This was followed by deposition of Pd(OAc) 2 on Fe 3 O 4-NH 2 @MIL-101-NH 2 particles. The final catalyst was characterized with FT-IR, nitrogen physisorption, thermogravimetry (TGA), scanning electron microscopy (SEM) combined with energy dispersive X-ray analysis (EDX), transmission electron microscopy (TEM), vibrating sample magnetometry (VSM), wide-angle X-ray diffraction spectroscopy (XRD) and X-ray photoelectron spectroscopy (XPS). The prepared magnetic catalyst was effectively used in the Heck coupling reaction in the presence of an inorganic base. The reaction parameters such as the base type, amounts of catalyst and solvents, temperature, and substrates ratios were optimized. The catalyst was then magnetically separated, washed, and reused 7 times without losing significantly catalytic activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

et al. 2020

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“…Another highly porous copper MOF, Cu 2 N 2 (CO 2 ) 4 (537‐MOF) ( 43 ), was fabricated by Xu and co‐workers which shows remarkably high efficiency as a catalyst for synthesis of benzimidazoles via C−H functionalization under air atmosphere with broad substrates scope . This MOF catalyst has merits over previously reported MOF catalyst for C−H activation in respect that reaction set up required was only air condition instead of O 2 atmosphere.…”

Section: C−h Activation Reactionmentioning

confidence: 99%

“…TMOF‐1 [Cu(bpy) 2 (eds)] n ( 44 ) with Cu II as catalytic LASs shows quantitative yield for the conversion of 2‐methyloxirane to its corresponding cyclic carbonate. It proved to be superior over other Cu II carboxylate MOFs such as HKUST‐1 . Compound ( 46 ) is among the first ones which was able to catalyze the reaction under solvent‐free conditions and without the help of any co‐catalyst .…”

Section: Co2 Addition Reactionmentioning

confidence: 99%

Metal‐Organic Frameworks as Platform for Lewis‐Acid‐Catalyzed Organic Transformations

Yadav

Kanoo

2019

Chemistry An Asian Journal

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Metal-organicframeworks (MOFs)are highly promising Lewis acid catalysts;t hey either inherently possess Lewis acid sites (LASs) on it or the LASs can be generated through various post-synthetic methods, the later can be performed in MOFs in at rivial fashion. MOFs are suitable platform for catalysis because of its highly crystalline and porous nature.M oreover,w ith recent advancements, thermal and chemical stability is not ap roblem with many MOFs. In this Minireview, an enormousv ersatility of MOFs,i n terms of their microporosity/mesoporosity,s ize/shapes elec-tivity,c hirality,p ore size, etc.,h as been highlighted. These are advantageous for designing and performing various targeted organic transformations. Although, many organic transformations catalyzed by MOFs with LASs have been reported in the recent past. In this Minireview,w eh ave restricted ourselves to four important organic reactions:(i) cyanosilylation,( ii)Diels-Alder reaction, (iii)C ÀHa ctivation,a nd (iv) CO 2 -addition.T he discussion focuses mostly on the recentr eports (42 examples). Cyanosilylation ReactionCyanosilylation reaction which is nucleophillic addition of trimethylsilylcyanide (TMSCN) to carbonyl compounds producing cyanohydrins is av ery important organic transformation. Cyanohydrins are considered as versatile building blocks for fine chemicals, agrochemicals and pharmaceuticals, that is, a-hydroxyacids, b-hydroxyamines, a-aminonitriles, a-hydroxyketones and b-aminoalcohols. [41][42][43][44] In contrast to other toxic substancess uch as KCN, HCN and NaCN, TMSCN is ap referred reagent for cyanosilylation reactiona si ti se asy to handle, the SiÀCb ond has low dissociation energy andm ost importantly it [a] A.

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“…Many reports highlighting the importance for generation of open sites (on activation) in MOF to act as Lewis acid catalyst have been well documented in the literature . In this context, Claisen–Schmidt reaction, , Knoevenagel condensation, − epoxidation, , ring opening of epoxides, − hydrolysis, , Friedlander reaction, Friedel–Craft alkylation, , cyanosilylation, − acetalization, C–H activation, − cyclopropanation, Biginelli reactions, , aldol condensation reaction, Henry reaction, , carbonyl–ene reaction, Sonogashira reaction, Suzuki coupling, biomass valorization , cyclization reaction, CO 2 fixation, polymerization, and Diels–Alder reaction are a few examples of such reports. However, none of the work emphasizes understanding whether the generation of CUS in the metal sites is crucial in all MOF-catalyzed organic reactions.…”

Section: Introductionmentioning

confidence: 99%

HKUST-1 Metal Organic Framework as an Efficient Dual-Function Catalyst: Aziridination and One-Pot Ring-Opening Transformation for Formation of β-Aryl Sulfonamides with C–C, C–N, C–S, and C–O Bonds

et al. 2021

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Metal−organic frameworks (MOFs) are extensively used in catalysis due to their robust structure, well-defined periodic reaction centers, and high porosity. We report Cu 3 (BTC) 2 •(H 2 O) 3 (HKUST-1) as an efficient heterogeneous catalyst for aziridination of alkene and ring-opening reaction of activated aziridines. Furthermore, we demonstrate that the transfer of a nitrogen group from PhINTs to olefins and its analogue to give aziridines takes place at the coordinatively unsaturated Cu(II) site of Cu 3 (BTC) 2 −MOF; however, the ring opening of activated aziridines is controlled by the Cu(II) Lewis acid site, and generation of coordinative unsaturation by thermal activation of the MOF is not necessarily important. The key advantage of this catalytic approach is the direct formation of C−C, C−N, C−O, and C−S bonds yielding β-aryl sulfonamide derivatives through a simultaneous aziridination ring-opening reaction of the alkene in one pot using a single catalyst.

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Synergic effect of copper-based metal–organic frameworks for highly efficient C–H activation of amidines

Abstract: A Cu–MOF-catalyzed C–H functionalization of substituted amidines was developed for the facile and efficient synthesis of benzimidazoles.

Cited by 17 publications

References 55 publications

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

Synthesis and Characterization of Palladium Supported Amino Functionalized Magnetic-MOF-MIL-101 as an Efficient and Recoverable Catalyst for Mizoroki–Heck Cross-Coupling

Metal‐Organic Frameworks as Platform for Lewis‐Acid‐Catalyzed Organic Transformations

HKUST-1 Metal Organic Framework as an Efficient Dual-Function Catalyst: Aziridination and One-Pot Ring-Opening Transformation for Formation of β-Aryl Sulfonamides with C–C, C–N, C–S, and C–O Bonds

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