Refernces
10.1002/adsc.200700333
The research focuses on the copper-catalyzed multicomponent reactions (MCRs) of terminal alkynes, acid chlorides, and carbodiimides to synthesize functionalized propiolamidine derivatives. The study explores the efficiency of various bases and solvents to optimize the reaction conditions. The optimal catalytic system was found to be a combination of CuI, triethylamine (TEA), and acetonitrile (CH3CN), yielding the desired products in good to excellent yields. The experiments involved a suspension of carbodiimide and acid chloride, followed by the addition of anhydrous acetonitrile, TEA, CuI, and alkyne at room temperature under a nitrogen atmosphere. The reaction mixture was stirred, then extracted with CH2Cl2, washed with saturated NaHCO3 solution and water, dried over anhydrous MgSO4, and evaporated under vacuum. The residue was purified using silica gel column chromatography with petroleum ether/ethyl acetate as the eluent. The analysis of the reaction products was based on isolated yields, which were calculated based on the amount of N,N’-dialkylcarbodiimides used.
10.1016/j.jfluchem.2020.109516
The research focuses on the development of a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles using methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA) and copper (I) iodide, promoted by tetrabutylammonium iodide (TBAI). The study explores the synthesis of 1-aryl-4-trifluoromethyl-1,2,3-triazoles, which are important due to the unique properties of the 1,2,3-triazole ring and the significance of the trifluoromethyl group in pharmaceuticals and agrochemicals. The experiments involved the optimization of reaction conditions, including the evaluation of different solvents, copper sources, and additives, with a particular emphasis on the role of TBAI in enhancing conversion rates. The analyses used to monitor the progress and outcomes of the reactions included liquid chromatography-mass spectrometry (LCMS), high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and high-resolution mass spectrometry (HRMS). These techniques were crucial for characterizing the intermediates and final products, as well as for optimizing the reaction conditions to achieve the desired trifluoromethylated heterocycles with broad functional group tolerance and on a multi-gram scale.
10.1016/j.carres.2010.03.041
The research focuses on the synthesis and evaluation of a library of 21 α-D- and β-D-glucopyranosyl triazoles using CuI-catalyzed azide alkyne 1,3-dipolar cycloaddition (CuAAC), also known as 'click chemistry'. The study investigates the reactant tolerance, reaction rate, product structure, and glucosidase inhibitory properties of these synthesized compounds. The reactants used include isomeric α- and β-glucopyranosyl azides and various commercially available alkynes with different functional groups. The synthesis was optimized using different reaction conditions, including variations in temperature and solvent, and was analyzed using techniques such as NMR spectroscopy, ES mass spectrometry, and X-ray crystallography to confirm the structure and purity of the products. The synthesized triazoles were then assayed for their ability to inhibit sweet almond β-glucosidase (GH1) and yeast α-glucosidase (GH13), providing insights into the relationship between the anomeric configuration of the inhibitors and their inhibitory activity towards specific enzymes.
10.1016/0022-328X(87)85094-5
The research focuses on the palladium-catalyzed synthesis of substituted phenylethynylpentamethyldisilanes and phenylethynylheptamethyltrisilanes. The purpose of this study was to develop a method for synthesizing these organosilicon compounds, which are valuable precursors for the preparation of silacyclopropenes and silapropadienes, and have unique charge-transfer emission characteristics. The researchers concluded that good to excellent yields of substituted phenylethynylpentamethyldisilanes can be obtained by the reaction of iodo- or bromo-benzenes with ethynylpentamethyldisilane in the presence of catalytic amounts of bis(triphenylphosphine)palladium(II) chloride-cuprous iodide or tetrakis(triphenylphosphine)palladium(0)-cuprous iodide. The chemicals used in the process include bis(triphenylphosphine)palladium(II) chloride, cuprous iodide, tetrakis(triphenylphosphine)palladium(0), ethynylpentamethyldisilane, and various substituted bromo- or iodo-benzenes.
10.1016/j.tet.2017.02.063
The study titled "Copper-catalyzed N–H/S–H functionalization: A strategy for the synthesis of benzothiadiazine derivatives" by ?engül Dilem Do?an presents a novel copper-catalyzed method for synthesizing 1,2,4-benzothiadiazin-3(4H)-ones. The research highlights the direct construction of N–S bonds using readily available N-(2-mercaptophenyl)-N'-(phenyl)-ureas as starting materials. The copper catalyst, specifically copper(I) iodide, plays a crucial role in facilitating the N-H/S-H activation, leading to the formation of the desired benzothiadiazine derivatives under mild conditions. The reaction is performed in N,N-dimethylformamide (DMF) under molecular oxygen, showcasing high efficiency and step economy. The study demonstrates the versatility of the method by synthesizing a variety of benzothiadiazine derivatives with different substituents, including aromatic and aliphatic groups, without significant effects on the reaction outcome. The findings offer an efficient and environmentally benign approach to synthesizing biologically important benzothiadiazine compounds, which have applications in pharmaceuticals and as antiviral agents.
10.1055/s-0030-1258206
The study presents a copper(I)-catalyzed intramolecular C-O bond-forming cyclization approach for the synthesis of various substituted 1,4-benzodioxines, utilizing a BINOL-CuI complex as a catalyst. This method was effectively applied to the total synthesis of isovanillyl sweetening agents, specifically 5-(2,3-dihydro-1,4-benzodioxin-2-yl)-2-methoxyphenol and 5-(2,3-dihydro-1,4-benzoxathiin-2-yl)-2-methoxyphenol, which are known to be significantly sweeter than sucrose. The process involves a five-step synthesis from isovanillin, yielding the sweetening agents in 15.8% and 14.85% overall yields, respectively. The research also explores the scope and limitations of the method, discussing the impact of different ligands, copper salts, solvents, and bases on the reaction efficiency. The study further proposes a possible mechanism for the Ullmann-type intramolecular C-O coupling cyclization reaction and provides detailed experimental procedures, characterization data, and spectral information for the synthesized compounds.
10.1016/S1872-2067(12)60623-8
The research detailed in the document focuses on the development of an efficient method for the N-arylation of water-soluble amino alcohols with aryl iodides in an aqueous environment, utilizing Copper(I) iodide (CuI) as a catalyst. The study aims to synthesize N-aryl amines under mild conditions without the need for additional ligands or phase-transfer catalysts. The substrate-promoted action allows for the reaction to proceed with a small excess of amino alcohol, resulting in yields ranging from 64% to 93%. The experiments involved screening various bases and copper sources to optimize the reaction conditions, which were ultimately found to be most effective at 100 °C using KOH as a base with CuI as a catalyst. The scope of the reaction was explored with different amino alcohols and aryl iodides, demonstrating tolerance to a range of substituents and providing insight into electronic effects on reactivity. The products were characterized using 1H NMR and MS, and the yields were compared to literature data to confirm the success of the synthesis.
10.1016/j.tetlet.2012.04.094
The study presents a method for synthesizing sulfenyl pyrroles through copper-catalyzed sulfenylation reactions. The researchers used pyrroles as the core compounds and reacted them with organic disul?des or thiols as sulfur sources to introduce sulfenyl groups. Copper(I) iodide (CuI) was employed as the catalyst, with different amounts and conditions optimized for the reactions. The study found that using 3 mol % of CuI in DMSO at 110 °C under air atmosphere worked well for disul?des, while 5 mol % of CuI in DMSO at the same temperature but under nitrogen atmosphere was optimal for thiols. The reactions produced 2-sulfenyl pyrroles in good to excellent yields and with high selectivity, without the need for any ligands or additives. The study also explored the scope of this methodology with various substituted pyrroles, disul?des, and thiols, demonstrating its general applicability and potential for synthesizing complex sulfenyl pyrroles.
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