10.1039/c8nj00075a
The study focuses on the development of an efficient copper-mediated coupling method for the synthesis of diaryl sulfones from arylsulfonyl hydrazides and aryl iodides or bromides using cupric acetate as a catalyst and polyethylene glycol (PEG-400) as an eco-friendly solvent. The study explores the optimal reaction conditions, including the influence of different PEG chain lengths, various copper sources, and the necessity of an external base. The reaction's scope was investigated with a range of substituted aryl iodides and arylsulfonyl hydrazides, demonstrating good functional group tolerance and moderate to good yields. The experiments utilized techniques such as GC-MS analysis to detect products and radical inhibitors to probe the reaction mechanism, suggesting a plausible pathway involving the formation of a copper-arylsulfonyl intermediate.
10.1016/j.tetlet.2009.11.009
The research presents a study on the N-alkylation of poor nucleophilic amines and sulfonamide derivatives using a hydrogen autotransfer process catalyzed by copper(II) acetate. The main objective was to develop a selective and economical method for the monoalkylation of aromatic and heteroaromatic amines, as well as sulfonamides, using primary alcohols as the initial source of electrophiles. The experiments involved optimizing reaction conditions, including the amount of catalyst, type of base, solvent, and temperature, and evaluating the scope of the reaction with variously substituted benzylic alcohols and anilines. The analyses used to assess the success of the reactions included column chromatography for product isolation and GC–MS to detect byproducts. The study demonstrated that copper(II) acetate is an effective catalyst for this process, leading to high yields of the desired N-alkylated products, and also described a deprotection process for sulfonamides to obtain primary amines, offering an alternative to direct monoalkylation of ammonia.
10.1039/b813944j
The research focuses on the synthesis and characterization of a novel linear heterotrinuclear iron(III)-copper(II)-iron(III) complex derived from 5-ferrocenyl-2-aminotroponew, which exhibits strong intramolecular ferromagnetic coupling in solid states due to a spin polarization mechanism. The complex was designed to overcome the rarity of long-distance ferromagnetic coupling within molecules by employing 2-aminotropone as a new π-spacer that can effectively chelate metals and allow for through-bond magnetic coupling. The synthesis involved Negishi coupling to form the precursor ligand, followed by reaction with copper(II) acetate to obtain the copper(II) complex. Electrochemical oxidation was used to prepare the 12+ complex. The experiments included X-ray crystallography to determine the molecular and packing structures, UV-Vis-NIR and ESR spectroscopy to analyze electronic absorption and magnetic properties, and SQUID magnetometry to measure magnetic behavior. Theoretical DFT calculations were also performed to estimate electronic structures and support the observed ferromagnetic coupling. The analyses revealed that the complex showed intramolecular ferromagnetic coupling and intermolecular antiferromagnetic coupling, with the spin polarization mechanism being confirmed through the calculated spin densities.
10.1039/c0dt01176b
The research focuses on the synthesis and characterization of copper(II) complexes of hybrid hydroxyquinoline-thiosemicarbazone ligands, which are designed to inhibit glycogen synthase kinase 3b (GSK3b) by increasing intracellular copper concentrations. The study investigates the potential of these complexes as therapeutic agents for Alzheimer's disease, which is associated with the hyper-phosphorylation of the protein tau due to increased GSK3b activity. The experiments involve the synthesis of tetradentate hybrid proligands and their copper(II) complexes, which are characterized using techniques such as single crystal X-ray crystallography, electrochemical analysis, and UV/Vis absorbance to assess stability. The complexes are tested for cell membrane permeability in neuronal-like SH-SY5Y cells, and their effects on intracellular copper concentrations and GSK3b inhibition are evaluated. The reactants used include 2-formyl-8-hydroxyquinoline, 4-N-substituted-3-thiosemicarbazides, and copper(II)acetate, while analyses employed encompass inductively coupled plasma mass spectrometry (ICP-MS) for metal content, Western blot for protein analysis, and various spectroscopic methods to confirm complex formation and purity.
10.1021/ol402471y
The study aimed to develop a method for the installation of trifluoromethyl groups onto aromatic scaffolds, which can enhance the metabolic stability and lipophilicity of pharmaceuticals and biologically active molecules. The researchers found that the addition of H2O and Ag2O was crucial for achieving good yields. Key chemicals used in the process include Pd(OAc)2 as the catalyst, Cu(OAc)2, TFA (trifluoroacetic acid), and the electrophilic trifluoromethylation reagent 3. The optimized conditions allowed for the synthesis of ortho-trifluoromethylated benzylamines with good yields, demonstrating the potential utility of this protocol in the functionalization of benzylamines for medicinal applications.
10.1055/s-0029-1218311
The study, titled "Design and Synthesis of Chiral Imidazolidine-Pyridine Ligands," investigates the creation and application of chiral imidazolidine-pyridine compounds as ligands in catalytic asymmetric reactions. The researchers synthesized these ligands through the condensation of chiral diamines and aldehydes, achieving high diastereoselectivities. The synthesized compounds were then examined for their ability to act as chiral ligands in the Cu(OAc)2-catalyzed Henry reaction. The study found that the newly synthesized imidazolidine-pyridine ligands, particularly L2b, effectively catalyzed the Henry reaction, yielding products with moderate to good enantiomeric excesses. The research highlights the potential of these ligands in asymmetric catalysis and suggests further exploration of diverse imidazolidine-containing ligands for various catalytic applications.
10.1002/chem.200802652
The research study on the competitive reactions between ethyl nitroacetate and electron-deficient olefins under various reaction conditions and catalysts. The purpose of the study was to understand how these reactions could be modulated to favor either Michael additions or cycloaddition-condensations, leading to the formation of either Michael adducts or isoxazole derivatives, respectively. The researchers concluded that the reactions could be selectively steered towards one product or the other by adjusting the strength of the base and the presence of a copper(II) catalyst. Key chemicals used in the process included ethyl nitroacetate as the primary nitro compound, various electron-deficient olefins as dipolarophiles, and bases such as DABCO, DBU, and NMP, as well as copper(II) acetate as a catalyst. The study demonstrated that by manipulating the catalytic system, one could selectively form either Michael adducts or isoxazoline cycloadducts, marking the first report on such selective formation from primary nitro compounds through modulation of the catalytic system.
10.1016/j.poly.2009.06.056
The research investigates the formation of supramolecular dimers in copper(II) complexes through hydrogen bonding and their impact on magnetic properties. The study focuses on three copper(II) complexes: [Cu(3-O2Nbz)2(nia)(H2O)2] (1), [Cu(4O2Nbz)2(nia)2(H2O)2] (2), and [Cu(4-O2Nbz)2(nia)2]?(4-O2NbzH)2 (3), where 3-O2Nbz and 4-O2Nbz represent 3-nitrobenzoate and 4-nitrobenzoate anions, respectively, and nia represents nicotinamide. These chemicals play crucial roles in the formation of the complexes. The research involves the synthesis of these complexes using copper(II) acetate, nicotinamide, and either 3-nitrobenzoic acid or 4-nitrobenzoic acid. The structures of the complexes were determined through X-ray crystallography, revealing that complex (1) forms supramolecular dimers with strong hydrogen bonds between equatorially coordinated water molecules and uncoordinated carboxylate oxygen atoms, leading to antiferromagnetic interactions. The study provides experimental evidence that hydrogen bonds extended through carboxylate bridges can serve as pathways for spin–spin interactions, as demonstrated by the magnetic properties and EPR spectra of the complexes.