A readily available urea based MOF that act as a highly active heterogeneous catalyst for Friedel-Crafts reaction of indoles and nitrostryenes

Zhu, Chengfeng; Mao, Qingqing; Li, De; Li, Changda; Zhou, Yiyang; Wu, Xiang; Luo, Yanqi; Li, Yougui

doi:10.1016/j.catcom.2017.10.010

Cited by 45 publications

(31 citation statements)

References 35 publications

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“…As shown in Figure 1b, the 2D 4 4 net consists of chair-like units, similar to that found in other related V-shape ditopic linkers [68,69,70]. Table 1 summarizes the parameters for each of the structures in this work and in comparison with some related structures where there is a 1,3-benzene moiety instead of a m -carborane unit [68,69,70]. In each 4 4 unit in our structures, two consecutive carborane clusters are above the plane containing the paddlewheel [Cu 2 (COO) 4 ] units, and the other two are below the plane.…”

Section: Resultssupporting

confidence: 85%

“…Thus, the bent L1 linkers and noncoplanar phenyl rings in 1-Solv adopt a 4 4 -grid topology by bending alternately above and below the plane containing the paddlewheel [Cu 2 (COO) 4 ] units to produce a very corrugated 2D layers. As shown in Figure 1b, the 2D 4 4 net consists of chair-like units, similar to that found in other related V-shape ditopic linkers [68,69,70]. Table 1 summarizes the parameters for each of the structures in this work and in comparison with some related structures where there is a 1,3-benzene moiety instead of a m -carborane unit [68,69,70].…”

Section: Resultssupporting

confidence: 76%

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A Reversible Phase Transition of 2D Coordination Layers by B–H∙∙∙Cu(II) Interactions in a Coordination Polymer

et al. 2019

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Materials that combine flexibility and open metal sites are crucial for myriad applications. In this article, we report a 2D coordination polymer (CP) assembled from CuII ions and a flexible meta-carborane-based linker [Cu2(L1)2(Solv)2]•xSolv (1-DMA, 1-DMF, and 1-MeOH; L1: 1,7-di(4-carboxyphenyl)-1,7-dicarba-closo-dodecaborane). 1-DMF undergoes an unusual example of reversible phase transition on solvent treatment (i.e., MeOH and CH2Cl2). Solvent exchange, followed by thermal activation provided a new porous phase that exhibits an estimated Brunauer-Emmett-Teller (BET) surface area of 301 m2 g−1 and is capable of a CO2 uptake of 41 cm3 g−1. The transformation is reversible and 1-DMF is reformed on addition of DMF to the porous phase. We provide evidence for the reversible process being the result of the formation/cleavage of weak but attractive B–H∙∙∙Cu interactions by a combination of single-crystal (SCXRD), powder (PXRD) X-ray diffraction, Raman spectroscopy, and DFT calculations.

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Section: Resultssupporting

confidence: 85%

Section: Resultssupporting

confidence: 76%

A Reversible Phase Transition of 2D Coordination Layers by B–H∙∙∙Cu(II) Interactions in a Coordination Polymer

et al. 2019

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“…However, due to their low chemical and thermal stability, these are not applicable for reactions that require severe conditions [3,7,49,50]. MOFs were used as a catalyst or catalyst supports for a diversity of organic transformations including Friedel-Crafts reactions [51][52][53][54][55], Knoevenagel condensation [56][57][58][59][60], aldol condensation [61][62][63], oxidation [64][65][66][67], coupling reactions [68][69][70][71][72][73][74][75], cyano silylation [15,76,77], carbon dioxide fixation [78,79], etc ( Fig. 1).…”

Section: Mofs As Heterogeneous Catalystsmentioning

confidence: 99%

“…Zhu and co-workers [51] developed a novel urea-containing metal-organic framework and used for Friedel-Crafts reaction of nitrostyrenes and indoles. They were found to be efficient with excellent product yields at low catalyst loadings.…”

Section: Friedel-crafts Reactionmentioning

confidence: 99%

Synthesis and catalytic applications of metal–organic frameworks: a review on recent literature

Remya¹,

Kurian²

2018

Int Nano Lett

170

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Metal-organic frameworks (MOFs) are an emerging class of porous materials created by the assembly of inorganic connectors and organic linkers. They have potential applications in fields such as gas storage as well as separation, sensing, catalysis, and drug delivery due to its properties such as flexibility, porosity, high surface area and functionality. Among the various synthetic approaches for the preparation of MOFs, solvothermal and microwave-assisted methods are of particular importance, and hence have been used frequently. They have been recently used as heterogeneous catalysts in Friedel-Crafts reactions, condensations reactions, oxidations, coupling reactions, etc. However, owing to the low thermal stability and moisture sensitivity, their catalytic applications are limited. This short review covers recent developments in the synthetic methods employed for the preparation of MOFs as well as their catalytic applications. Keywords Metal-organic framework • Synthesis techniques • Stability • Heterogeneous catalyst Abbreviations H 2 2,3-pydc Pyridine-2,3-dicarboxylic acid bpp 1,3-Bis(4-pyridyl)propane H 2 bpabdc 2,5-Bis(phenylamino)-1,4-benzenedicarboxylic acid H 2 tdc Thiophene-2,5-dicarboxylic acid H 4 abtc 3,3′,5,5′-Azobenzene-tetracarboxylic acid ad Adenine H 3 btc 1,3,5-Benzene tricarboxylic acid H 2 bdc 1,4-Benzenedicarboxylic acid pdc 2,6-Pyridinedicarboxylate DMI 1,3-Dimethyl-2-imidazolidinone DMA N,N′-Dimethylacetamide DMF N,N′-Dimethyl formamide THF Tetrahydrofuran TBHP tert-Butyl hydroperoxide DMI 1,3-Dimethy-2-imidazolidinone

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“…Functionalizing MOFs with urea moiety yielded interesting results. Luo et al synthesized a MOF from V-shaped dicarboxylate ligands and dicopper units [ 77 ]. The obtained simple 2D structure was believed to ease the access of the substrates while stabilizing the urea moieties, previously attached to the building blocks.…”

Section: Synthetic Applications In Heterogeneous Systemsmentioning

confidence: 99%

Organic Synthesis Using Environmentally Benign Acid Catalysis

Kokel

Schäfer

Török

2019

COS

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Recent advances in the application of environmentally benign acid catalysts in organic synthesis are reviewed. The work includes three main parts; (i) description of environmentally benign acid catalysts, (ii) synthesis with heterogeneous and (iii) homogeneous catalysts. The first part provides a brief overview of acid catalysts, both solid acids (metal oxides, zeolites, clays, ion-exchange resins, metal-organic framework based catalysts) and those that are soluble in green solvents (water, alcohols) and at the same time could be regenerated after reactions (metal triflates, heteropoly acids, acidic organocatalysts etc.). The synthesis sections review a broad array of the most common and practical reactions such as Friedel-Crafts and related reactions (acylation, alkylations, hydroxyalkylations, halogenations, nitrations etc.), multicomponent reactions, rearrangements and ring transformations (cyclizations, ring opening). Both the heterogeneous and homogeneous catalytic synthesis parts include an overview of asymmetric acid catalysis with chiral Lewis and Brønsted acids. Although a broad array of catalytic processes are discussed, emphasis is placed on applications with commercially available catalysts as well as those of sustainable nature; thus individual examples are critically reviewed regarding their contribution to sustainable synthesis.

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A readily available urea based MOF that act as a highly active heterogeneous catalyst for Friedel-Crafts reaction of indoles and nitrostryenes

Cited by 45 publications

References 35 publications

A Reversible Phase Transition of 2D Coordination Layers by B–H∙∙∙Cu(II) Interactions in a Coordination Polymer

A Reversible Phase Transition of 2D Coordination Layers by B–H∙∙∙Cu(II) Interactions in a Coordination Polymer

Synthesis and catalytic applications of metal–organic frameworks: a review on recent literature

Organic Synthesis Using Environmentally Benign Acid Catalysis

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