Zinc(II) and Copper(II) Metal–Organic Frameworks Constructed from a Terphenyl‐4,4′′‐dicarboxylic Acid Derivative: Synthesis, Structure, and Catalytic Application in the Cyanosilylation of Aldehydes

Karmakar, Anirban; Paul, Anup; Rúbio, Guilherme M. D. M.; Silva, M. Fátima C. Guedes da; Pombeiro, Armando J. L.

doi:10.1002/ejic.201600902

Cited by 31 publications

(25 citation statements)

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“…Trimethylsilyl cyanide (TMSCN) is the most commonly used cyanide source for the formation of cyanohydrins105,106 , however the use of a catalyst is also necessary in order to activate both the substrate and the cyanide precursor. A 1D CP with relevant catalytic behavior was presented in 2016 by Pombeiro's group107 . The authors study the coordination capabilities of a rigid dicarboxylic acid ligand, named as 3,3′′-dipropoxy-[1,1′:4′,1′′-terphenyl]-4,4′′-dicarboxylic acid (H2dtda), with metal sources of 3d elements such as Zn(II) and Cu(II).…”

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confidence: 99%

Review: Recent advances of one-dimensional coordination polymers as catalysts

Loukopoulos

Kostakis

2018

Journal of Coordination Chemistry

100

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LIST OF ABBREVIATIONS0D = zero-dimensional 1,4-DHPs = 1,4-dihydropyridine 1D = one-dimensional 2,4-DNP = 2,4-nitrophenol 2D = two-dimensional 2L-H2asp = N-(2-pyridylmethyl)-L-aspartic acid 3D = three-dimensional 3L-val = N-(3-pyridylmethyl)-L-valine aq. = aqueous bbbi = 1,1'-(1,4-butanediyl)bis-1H-benzimidazole) bbmb = 1,2-bis((1H-benzo[d][1,2,3]triazol-1-yl)methyl)benzene bdob = 1,4-bis(4,5-dihydro-2-oxazolyl)benzene bipy = 4,4'-bipyridine bm = benzimidazole [(bmim)(BF4)] = 1-butyl-3-methylimidazolium tetrafluoroborate BMPyr = 1-butyl-1-methylpyrrolidinium btSe = benzene-1,2,4,5-tetraselenolate btt = benzene-1,2,4,5-tetrathiol CP = coordination polymer CR = Congo Red Cy = cyclohexane dfbi = 1,1'-(9,9-dimethyl-9H-fluorene-2,7-diyl)bis(1H-imidazole) D-H2pen = D-penicillamine DMF = N,N-dimethylformamide DMSO = Dimethylsulfoxide dped = 1,2-bis(diphenylphosphino)ethane dioxide dpppda = 1,4-N,N,N′,N′-tetra(diphenylphosphanylmethyl) benzene diamine ee = enantiomeric excess ESI-MS = electrospray ionization mass spectrometry EtOH = ethanol FTIR = Fourier-transform infrared spectroscopy Hbmmp = 4-ethyl-2,6-bis((E)-((3-morpholinopropyl)imino)methyl)phenol HPNP = 2-hydroxypropyl-p-nitrophenylphosphate Htbba = 4-((4-([2,2':6',2''-terpyridin]-4'-yl)benzyl)oxy)benzoic acid H2aipa = 5-acetamidoisophthalic acid H2bipa = 5-benzamidoisophthalic acid H2bpdc = 4,4'-biphenyldicarboxylic acid H2cybps = 1,2-cyclohexanediamino-N,N'-bis(3-tert-butyl-5-(4-pyridyl)salicylidene H2dtda = 3,3′′-dipropoxy-[1,1′:4′,1′′-terphenyl]-4,4′′-dicarboxylic acid H2hmb = 2-[(2-hydroxy-3-methoxyphenyl)methylideneamino]benzenesulfonic acid H2icyd = N,N'-bis-[(imidazol-4-yl)methylene]cyclohexane-1,2diamine H2ntp = 2-nitroterephthalic acid H2phba = 4-hydroxybenzoic acid H2ppd = bis(pyridin-2-ylmethylene)pyridine-2,6-dicarbohydrazide H2pydca = pyridine-2,6-dicarboxylate H2tae = 1,1,2,2-tetraacetylethane H3bes = N,N-bis(2-hydroxyethyl)-2-aminoethanesulfonic acid H3btc = 1,2,4-trimellitic acid H3ccb = 3-(carboxymethyl-amino)-4-chlorobenzoic acid H3cia = N-(4-carboxybenzyl) iminodiacetic acid H3dhia = 5-(2-(4,4-dimethyl-2,6-dioxocyclohexylidene)hydrazinyl)isophthalic acid H3dht = 2-(2-(4,4-dimethyl-2,6-dioxocyclo-hexylidene)hydrazinyl)terephthalic acid H3dmb = 2-[(2,3-dihydroxyphenyl)methylideneamino]benzenesulfonic acid H3tea = triethanolamine H4bccy = N,N′-bis(4-carboxysalicylidene)cyclohexanediamine H4bced = N,N'-bis(4-carboxysalicylidene)ethylenediamine H4hpd = bis(2-hydroxybenzylidene)pyridine-2,6-dicarbohydrazide H4pdada = 4,4'-((pyridine-2,6-dicarbonyl)bis(azanediyl))dibenzoic acid H4pma = pyromellitic acid H6bmt = (benzene-1,3,5-triyltris(methylene))triphosphonic acid H6nmp = nitrilotris(methylenephosphonic acid) IL = ionic liquid iPrOH = 2-propanol MB = methylene blue MeCN = acetonitrile MeOH = methanol MO = Methyl Orange MOF = metal-organic framework MW = microwave NB = nitrobenzene NMF = N-Methylformamide NTf2 = bis(trifluoromethanesulfonyl)imide PhIO = iodosobenzene pmba = 2-(2-pyridylmethyleneamino)benzenesulfonic acid PNP = paranitrophenol RhB = Rh...

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confidence: 99%

Review: Recent advances of one-dimensional coordination polymers as catalysts

Loukopoulos

Kostakis

2018

Journal of Coordination Chemistry

100

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“…For a long time, our group has been utilizing this technique for carrying out many catalytic transformations [ 22 ]. Recently, various CPs have been explored for cyanosilylation of aldehydes under conventional conditions [ 23 ]; however, microwave-assisted cyanosilylation of aldehydes catalyzed by CPs has not yet been significantly studied. Thus, the exploration of appropriate CP based catalysts for the microwave-assisted solvent-free cyanosilylation of aldehydes is a topic of great interest.…”

Section: Introductionmentioning

confidence: 99%

Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes

et al. 2021

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The new coordination polymers (CPs) [Zn(μ-1κO1:1κO2-L)(H2O)2]n·n(H2O) (1) and [Cd(μ4-1κO1O2:2κN:3,4κO3-L)(H2O)]n·n(H2O) (2) are reported, being prepared by the solvothermal reactions of 5-{(pyren-4-ylmethyl)amino}isophthalic acid (H2L) with Zn(NO3)2.6H2O or Cd(NO3)2.4H2O, respectively. They were synthesized in a basic ethanolic medium or a DMF:H2O mixture, respectively. These compounds were characterized by single-crystal X-ray diffraction, FTIR spectroscopy, thermogravimetric and elemental analysis. The single-crystal X-ray diffraction analysis revealed that compound 1 is a one dimensional linear coordination polymer, whereas 2 presents a two dimensional network. In both compounds, the coordinating ligand (L2−) is twisted due to the rotation of the pyrene ring around the CH2-NH bond. In compound 1, the Zn(II) metal ion has a tetrahedral geometry, whereas, in 2, the dinuclear [Cd2(COO)2] moiety acts as a secondary building unit and the Cd(II) ion possesses a distorted octahedral geometry. Recently, several CPs have been explored for the cyanosilylation reaction under conventional conditions, but microwave-assisted cyanosilylation of aldehydes catalyzed by CPs has not yet been well studied. Thus, we have tested the solvent-free microwave-assisted cyanosilylation reactions of different aldehydes, with trimethylsilyl cyanide, using our synthesized compounds, which behave as highly active heterogeneous catalysts. The coordination polymer 1 is more effective than 2, conceivably due to the higher Lewis acidity of the Zn(II) than the Cd(II) center and to a higher accessibility of the metal centers in the former framework. We have also checked the heterogeneity and recyclability of these coordination polymers, showing that they remain active at least after four recyclings.

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“…Numerous catalysts, including Lewis acids [8][9][10], Lewis bases [11][12][13], oxazaborolidinium ion [14,15], amino-thiourea [16,17], organic-inorganic salts [18][19][20][21][22], N-heterocyclic carbenes [23,24], nonionic bases [25,26], Ti,Al-phosphine oxide bifunctional species with carbohydrate or binaphthol scaffolds [27][28][29], Ti,Al-N-oxide bifunctional catalysts with proline, pyrrolidine and 1,2-diamino ligands [30][31][32], V-, Mn-, Al-, and Ti-salen complexes [33][34][35][36], chiral Ti-α,α,α,α-1,3-dioxolane-tetraaryl-4,5-dimethanols [37,38], Cu(II) and Co(II/III) hydrazone complexes [39,40] and also metal organic frameworks (MOFs) [41][42][43][44], have been developed for this transformation. According to the proposed reaction mechanism [1], the coordination or carbohydrate or binaphthol scaffolds [27][28][29], Ti,Al-N-oxide bifunctional catalysts with proline, pyrrolidine and 1,2-diamino ligands [30][31]…”

Section: Introductionmentioning

confidence: 99%

“…Thus, the reaction rate and yield of cyanohydrin trimethylsilyl ethers are strongly dependent on the nature of metal center and the coordinated ligand in the metal complex catalyzed cyanation reaction [1]. MOFs or coordination polymers are attractive not only as storage, transporter, magnetic and luminescence materials [45][46][47][48], but also as catalysts for various catalytic transformations, such as alkane/alcohol oxidation [49,50], C-C bond formation [40,44], etc., from the viewpoint of green chemistry. The design and synthesis of coordination polymer catalysts, in particular being inexpensive, highly efficient and selective with a wide range of substrates, remains a challenging goal in cyanosilylation reaction.…”

Section: Introductionmentioning

confidence: 99%

Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media

et al. 2019

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The novel Ag(I) and Cu(II) coordination polymers [Ag(μ3-1κO;2:3κO′;4κN-HL)]n∙n/2H2O (1) and [Cu(en)2(μ-1κO;2κN-L)]n∙nH2O (2) [HL− = 2-(2-(1-cyano-2-oxopropylidene)hydrazinyl)benzene sulfonate] were synthesized and characterized by IR and ESI-MS spectroscopies, elemental and single crystal X-ray diffraction analyses. Compounds 1 and 2 as well as the already known complex salt [Cu(H2O)2(en)2](HL)2 (3) have been tested as homogenous catalysts for the cyanosilylation reaction of different aldehydes with trimethylsilyl cyanide, to provide cyanohydrin trimethylsilyl ethers. Coordination polymer 2 was found to be the most efficient one, with yields ranging from 76 to 88% in methanol, which increases up to 99% by addition of the ionic liquid [DHTMG][L-Lactate].

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Zinc(II) and Copper(II) Metal–Organic Frameworks Constructed from a Terphenyl‐4,4′′‐dicarboxylic Acid Derivative: Synthesis, Structure, and Catalytic Application in the Cyanosilylation of Aldehydes

Cited by 31 publications

References 100 publications

Review: Recent advances of one-dimensional coordination polymers as catalysts

Review: Recent advances of one-dimensional coordination polymers as catalysts

Pyrene Carboxylate Ligand Based Coordination Polymers for Microwave-Assisted Solvent-Free Cyanosilylation of Aldehydes

Cyanosilylation of Aldehydes Catalyzed by Ag(I)- and Cu(II)-Arylhydrazone Coordination Polymers in Conventional and in Ionic Liquid Media

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