Category: copper-catalyst

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Chelating and bridging bis(diphenylphosphino)aniline complexes of copper(I)

The ligand bis(diphenylphosphino)aniline (dppan) has been shown to be a versatile ligand sporting different coordination modes and geometries as dictated by copper(I) and the counter ion. The molecular structures of its Cu(I) complexes were characterized by X-ray crystallography. The ligand was found in a chelating mode and monomeric complexes were formed when the ligand to copper ratio was 2:1 and the anion was non-coordinating. However, with thiocyanate as the counter anion, the ligand was found to adopt two different modes, with one ligand chelating and the other acting as a monodentate ligand. With CuX (X = Cl, Br), dppan formed a tetrameric complex when the ligand and metal were reacted in the ratio of 1:1. But reactions containing ligand and metal in the ratios of 1:2 or 2:1, resulted in the formation of a mixture of species in solution. Crystallization however, led to the isolation of the tetrameric complex. Variable temperature 31P{1H} NMR spectra of the isolated tetramers did not show the presence of chelated structures in solution. Tetra-alkylammonium salts were added to solutions of various complexes of dppan and studied by 31P{1H} NMR to probe the effect of anions on the stability of complexes in solution. The Cu-dppan complexes were robust and did not interconvert with other structures in solution unlike the bis(diphenylphosphino)isopropylamine complexes.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Thiazolidine derivatives use

A thiazolidine derivative of the formula: STR1 wherein R1 is hydrogen, hydroxyl, lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms, or lower carboxylic acyloxy having 2 to 4 carbon atoms; each of R2 and R3 is hydroxyl, lower alkyl having 1 to 4 carbon atoms, lower alkoxy having 1 to 4 carbon atoms or lower carboxylic acyloxy having 2 to 4 carbon atoms or pharmaceutically acceptable salt thereof a is a novel compound having antiulcer activity and inhibitory effect on gastric acid secretion. The compound is useful as antiulcer agent or inhibitory agent of gastric acid secretion.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Two novel nanoporous supramolecular architectures based on copper(I) coordination polymers with uniform (8, 3) and (8210) nets: In situ formation of tetrazolate ligands

The hydro/solvothermal reactions of Cu(I)/Cu(II) salt, NaN3, and acetonitrile in water or methanol yield two noninterpenetrated supramolecular networks containing 1D hexagonal and square nanochannels, {[Cu(Mtta)]¡¤0.17H2O}n (1) and its pseudopolymorph [Cu(Mtta)]n (2) (Mtta = 5-methyl tetrazolate), involving ligand insitu formation by cycloaddition of nitriles and azides. The copper-(I) centers in both complexes are all bridged by Mtta ligands, forming the different shapes of the cavity. 1 exhibits an unprecedented uniform (8, 3) topological metal network, whereas 2 is a 3-connected (8210) metal net.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Sandmeyer difluoromethylation of (hetero-)arenediazonium salts

A Sandmeyer-type difluoromethylation process has been developed that allows the straightforward conversion of (hetero-)arenediazonium salts into the corresponding difluoromethyl (hetero-)arenes under mild conditions. The actual difluoromethylating reagent, a difluoromethyl-copper complex, is formed in situ from copper thiocyanate and TMS-CF2H. The diazonium salts are either preformed or generated in situ from broadly available aromatic amines.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Ligand-controlled mixed-valence copper rectangular grid-type coordination polymers based on pyridylterpyridine

Six mixed-valence CuICuII compounds containing 4?-(4-pyridyl)-2,2?:6?,2?-terpyridine (L1) or 4?-(2-pyridyl)-2,2?:6?,2?-terpyridine (L2) were prepared under the hydrothermal and ambient conditions, and their crystal structures were determined by single-crystal X-ray diffraction. Selection of CuCl 2¡¤2H2O or Cu(CH3COO)2¡¤ H2O with the L1 ligand and NH4SCN, KI, or KBr under hydrothermal conditions afforded 1-dimensional mixed-valence Cu ICuII compounds [Cu2(L1)(mu-1,1-SCN)(mu-Cl) Cl]n (1), [Cu2(L1)(mu-l)2Cl]n (2), [Cu2(L1)(mu-Br)2Br]n (3), and [Cu 2(L1)(mu-1,3-SCN)2(SCN)]n (4), respectively. Compound 5, prepared by layering with CuSCN and L1, is a 2-dimensional bilayer structure. In compounds 1-5, the L1 ligand and X (X = Cl, Br, I, SCN) linked between monovalent and divalent copper atoms resulting in the formation of mixed-valence rectangular grid-type M4L4 or M 6L6 building blocks, which were further linked by X (X = Cl, Br, I, SCN) to form 1- or 2-dimensional polymers. The sizes of M 4L4 units in 1-4 were fine-tuned by the sizes of X linkers. Reaction of Cu(CH3COO)2¡¤H2O with L2 and NH4SCN under hydrothermal conditions gave mixed-valence CuICuII compound [Cu2(L2)(mu-1,3-SCN) 3]n (6). Unlike those in 1-5, the structure of 6 was constructed from thiocyanate groups and the pendant pyridine of L2 left uncoordinated. The temperature-dependent magnetic susceptibility studies on compounds 1 and 4 showed the presence of mixed-valence electronic structure.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Synthetic, spectral, structural and catalytic activity of infinite 3-D and 2-D copper(ii) coordination polymers for substrate size-dependent catalysis for CO2 conversion

Two copper(ii) coordination polymers, viz. [Cu2(OAc)4(mu4-hmt)0.5]n (1) and [Cu{C6H4(COO-)2}2]n¡¤2C9H14N3 (2), have been synthesized solvothermally and characterized. The solid-state structure reveals that 1 is an infinite three-dimensional (3D) motif with fused hexagonal rings consisting of Cu(ii) and hmt in a mu4-bridging mode, while 2 is an infinite two dimensional (2D) motif containing Pht-2 in a mu1-bridging mode. CP 1 has a two-fold interpenetrated diamondoid network composed of 4-connected sqc6 topology with the point symbol of {66}, while 2 has a Shubnikov tetragonal plane network possessing a 4-connected node with an sql topology with a point symbol of {44¡¤.62}-VS [4¡¤4¡¤4¡¤4¡¤?¡¤?]. Both CPs 1 and 2 serve as efficient catalysts for CO2-based chemical fixation. Moreover, 1 demonstrates one of the highest reported catalytic activity values (%yield) among Cu-based MOFs for the chemical fixation of CO2 with epoxides. 1 shows high efficiency for CO2 cycloaddition with small epoxides but its catalytic activity decreases sharply with the increase in the size of epoxide substrates. The catalytic results suggested that the copper(ii) motif-catalyzed CO2 cycloaddition of small substrates had been carried out within the framework, while large substrates could not enter into the framework for catalytic reactions. The high efficiency and size-dependent selectivity toward small epoxides on catalytic CO2 cycloaddition make 1 a promising heterogeneous catalyst for carbon fixation and it can be used as a recoverable stable heterogeneous catalyst without any loss of performance. The solvent-free synthesis of the cyclic carbonate from CO2 and an epoxide was monitored by in situ FT-IR spectroscopy and an exposed Lewis-acid metal site catalysis mechanism was proposed.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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A decade of advances in the reaction of nitrogen sources and alkynes for the synthesis of triazoles

The cyclization reactions of alkynes have become one of the most important and useful methodologies for the preparation of heterocycles. To this end, the association between alkynes and nitrogen sources are versatile substrates for the synthesis of triazole derivatives. The improvement in the synthesis of triazoles by the use of copper catalysts in cycloaddition reactions, as well as the significant advances obtained with the use of other transition metals, such as gold, iridium, iron, nickel, ruthenium, samarium, silver, and zinc, to promote the cyclization of alkynes and nitrogen sources are addressed in this review. Furthermore, there has been a significant interest in recent years in developing simple, clean, non-toxic, cost-effective and eco-friendly protocols. In this sense, the reaction of alkynes with nitrogen sources, in the complete absence of transition metals, reaches many of these requirements becoming a good alternative to the synthesis of triazoles. For this reason, the last topic of this review deals with the synthesis of triazoles using alkynes and nitrogen sources under transition metal-free conditions.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Fura-2FF-based calcium indicator for protein labeling

We describe the synthesis and fluorescence properties of a Fura-2FF-based fluorescent Ca2+ indicator that can be covalently linked to SNAP-tag fusion proteins and retains its Ca2+ sensing ability after coupling to protein. The Royal Society of Chemistry 2010.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

Application of 1111-67-7, Chemistry is the science of change. But why do chemical reactions take place? Why do chemicals react with each other? The answer is in thermodynamics and kinetics.In a document type is Article, and a compound is mentioned, 1111-67-7, Cuprous thiocyanate, introducing its new discovery.

Doping CuSCN films for enhancement of conductivity: Application in dye-sensitized solid-state solar cells

Construction of dye-sensitized solid-state solar cells requires high band-gap (therefore, transparent) hole collectors which can be deposited on a dye-coated nanocrystalline semiconductor surface without denaturing the dye. Copper (I) thiocyanate (CuSCN) is an important p-type semiconductor satisfying the above requirements. However, the conductivity of this material, which depends on excess SCN, is not sufficiently high and polymerization of SCN prevents incorporation of sufficient amount of excess SCN during the process of synthesis of CuSCN. We have found that the conductivity of solid CuSCN can be increased by exposure to halogen gases which generate SCN or to a solution of (SCN)2 in CCl4. The latter method is suitable for doping of CuSCN films in dye-sensitized solid-state solar cells.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”

 

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Subtle side chain effect of methyl substituent on the self-assembly of polypseudorotaxane complexes: Syntheses, structural diversity and photocatalytic properties

Cation-templated self-assembly of 1,n-bis(4-methylpyridine)alkane cations (n = 3-7) with CuSCN was studied and a series of new polymeric thiocyanate frameworks were obtained: {(bmpp)[Cu2Br2(SCN)2]}n (1), {(bmpt)[Cu2(SCN)4]}n (2), {(bmppt)[Cu2(SCN)4]}n (3), {(bmph)[Cu4(SCN)6]}n (4), {(bmphp)[Cu2(SCN)4]}n (5), (n = 3, bmpp; n = 4, bmpt; n = 5, bmppt; n = 6, bmph; n = 7, bmphp). The structures consist of 1-2D frameworks with the dications trapped within host network cavities. Compounds 1, 2, 3 and 5 possess the infinite two-dimensional polypseudorotaxane anion networks. Compound 4 has a novel 1D chain structure which looks like lotus root. The results demonstrate that the side chain of methyl substituent plays an important role in the fabrication of polypseudorotaxane structures. Furthermore, solid UV-Vis spectra, photoluminescence and photocatalytic properties at ambient temperature were also investigated.

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Reference£º
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”