10.1016/j.tetlet.2011.01.003
The study develops an efficient and environmentally friendly method for the N-arylation of amides using aryl halides, catalyzed by ligand-free copper(I) oxide (Cu2O) in water. This method provides a practical approach to synthesizing N-arylated amides, which are valuable in pharmaceuticals and materials science. The research focuses on optimizing reaction conditions, including the choice of copper catalyst, base, and phase-transfer catalyst, to achieve good to excellent yields of the desired N-arylated products. The method proves effective for a variety of amides and aryl iodides, making it a versatile tool for organic synthesis.
10.1002/ejoc.200500055
The research focuses on the synthesis of shape-persistent polyaldehyde (polyal) dendrimers, which are further transformed into polyene and polyyne dendrimers. These dendrimers are constructed using a divergent iterative method, with 1,3,5-triethynylbenzene as the core unit and 2-bromo-5-tert-butyl-1,3-benzenedicarbaldehyde as the building block. The study involves the use of Sonogashira coupling and Corey-Fuchs reaction as key synthetic strategies. Various reactants, including 1,3,5-triethynylbenzene, 2-bromo-5-tert-butyl-1,3-benzenedicarbaldehyde, iodobenzene, and phosphorus-based reagents, are utilized in the synthesis process. The synthesized dendrimers are analyzed using techniques such as NMR spectroscopy, mass spectrometry, and UV/Vis spectroscopy to confirm their structures and properties. The research also explores the thermal stability and fluorescence emission of the synthesized dendrimers, providing insights into their potential applications in electronics, photonics, and materials science.
10.1002/cssc.201901813
The research aims to develop a visible-light-activated Sonogashira C–C coupling reaction at room temperature using single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) as a catalyst. This method avoids the need for cocatalysis by TiO2 and offers a more sustainable and cost-effective alternative to traditional Sonogashira coupling reactions, which typically require expensive Pd catalysts and harsh conditions. The key chemicals used in this study include aryl halides (such as iodobenzene), terminal alkynes (like phenylacetylene), Cu2O TNCs, and CO2. The study concludes that CO2 enhances the formation of a light-absorbing surface-bound CuI-phenylacetylide complex on Cu2O TNCs, which facilitates single-electron transfer with aryl halides to enable efficient C–C bond formation. The Cu2O TNCs catalyst demonstrated good recyclability and maintained high catalytic efficiency over multiple cycles, making it a promising candidate for industrial applications.
10.1016/j.chempr.2019.07.023
This study presents a novel dimeric gold-catalyzed oxidative cross-coupling method for the synthesis of a diverse range of biaryl compounds using arylboronates and arylsilanes. The method overcomes the limitations of traditional gold-catalyzed o,p-orientation rules and is effective for electron-rich arenes through C–H bond activation. It exhibits excellent tolerance for various functional groups and offers a flexible synthetic approach to (pseudo)halogenated biaryls. The research demonstrates the unique catalytic efficiency of a dimeric gold complex and the preparation of biaryl pharmacophores under pseudoneutral conditions, which is significant for the synthesis of complex organic materials and pharmaceuticals. The study also includes the successful synthesis of several biaryl pharmacophores and p-conjugated organic materials, highlighting the method's synthetic value and versatility.
10.1016/j.tetlet.2013.03.114
The study presents the first Pd-catalyzed α-arylation of thioamides, exploring their use in coupling chemistry as carbon nucleophiles for transition-metal-catalyzed C–C coupling reactions. Thioamides, which contain sulfur, nitrogen, and an α-carbon as adjacent nucleophilic centers, are significant synthetic building blocks. In this research, a variety of α-arylated thioamides were synthesized in moderate to good yields under mild conditions, offering a new synthetic transformation for thioamides and an alternative method to access functionalized thioamides. Key chemicals used include N,N-dimethyl-3-phenylpropanethioamide (thioamide 1a), iodobenzene (aryl halide 2a), and [Pd(C3H5)Cl]2 (a palladium catalyst), along with phosphine ligand PPh3. These chemicals served to facilitate the coupling reaction, with the palladium catalyst playing a crucial role in the C–C bond formation, and the phosphine ligand enhancing the reaction's efficiency. The study also demonstrated high chemoselectivity for thioamides over amides in the reaction.
10.1039/b718642h
The research focuses on the development of a novel purification strategy for iodine(III)-promoted glycosidations of 2-deoxy diethyldithiophosphate glycosides using a tagged iodine(III)-promoter. The purpose of this study was to address the challenges associated with the removal of by-products, such as iodobenzene, which are common in hypervalent iodine chemistry and can be cumbersome to remove chromatographically. The researchers introduced a concept based on a sulfonate ester tag that acts as a dormant ion exchange group, allowing for the liberation and removal of the sulfonate anion via an SN2-step and subsequent anion exchange resin capture. The tagged iodine(III) reagents were prepared from commercially available p-iodo-benzenesulfonyl chloride (pipsyl chloride) and were used to activate glycosyl donors in the presence of various glycosyl acceptors. The study concluded that this method, combined with a scavenging protocol, is a powerful glycosidation approach for diethyldithiophosphates and has general applicability for purification protocols of reagents and catalysts. Key chemicals used in the process include p-iodo-benzenesulfonyl chloride, i-butyl sulfonate, bis(acetoxy)iodoarene, iodosylbenzene, and the Zefirov reagent, as well as various glycosyl donors and acceptors such as diethyldithiophosphates and decarestrictines.
10.1002/anie.201803228
The study presents a nickel-catalyzed reductive cross-coupling method for the late-stage monofluoroalkylation of aryl halides with unactivated fluoroalkyl halides. The key to this method's success lies in the combination of diverse readily available nitrogen ligands, specifically bidentate and monodentate pyridine-type ligands, which generate easily tunable catalysts. This approach enables the synthesis of fluoroalkylated drug-like molecules under mild conditions with high efficiency and excellent functional group tolerance. The researchers optimized the reaction conditions using phenyl iodide as the substrate and 1-fluoro-1-iodo ethylbenzene as the coupling partner, identifying dmbpy and 4-CN-Py as the optimal ligands. The method demonstrated broad scope, successfully fluorinating various aryl iodides and bromides, including those with electron-donating and withdrawing groups, as well as complex pharmaceuticals like Ezetimibe and Estrone. The study also extended the method to non-fluorinated alkyl halides, showing its potential for late-stage alkylation of drugs. Mechanistic studies suggested the involvement of a nickel-based catalytic cycle with a free monofluoroalkyl radical. This combinatorial catalysis strategy offers a solution for nickel-catalyzed reductive cross-coupling reactions and provides an efficient way to synthesize fluoroalkylated drug-like molecules for drug discovery.
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Xi:Irritant;
