9 research outputs found

    Palladium-Catalyzed Domino Cyclization/Alkylation of Terminal Alkynes: Synthesis of Alkynyl-Functionalized Azaindoline Derivatives

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    A novel palladium-catalyzed domino cyclization/alkylation of terminal alkynes was achieved for the synthesis of alkynyl-functionalized 3,3-disubstituted azaindoline derivatives under air atmosphere conditions. Various types of terminal alkynes, including aromatic alkynes, aliphatic alkynes, and ferrocene acetylene, can undergo the process successfully. The protocol provides a range of alkynyl-functionalized azaindoline scaffolds bearing a quarternary carbon center

    Palladium-Catalyzed Domino Heck/Intermolecular C–H Bond Functionalization: Efficient Synthesis of Alkylated Polyfluoroarene Derivatives

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    An efficient palladium-catalyzed alkylation of electron-deficient polyfluoroarenes is described. The protocol provides a useful and operationally simple access to a broad scope of alkylated polyfluoroarene derivatives in moderate to excellent yields. This also represents the first example of the introduction of a polyfluoroarene structure involving an alkylpalladium­(II) intermediate

    Palladium-Catalyzed Domino Heck/Intermolecular C–H Bond Functionalization: Efficient Synthesis of Alkylated Polyfluoroarene Derivatives

    No full text
    An efficient palladium-catalyzed alkylation of electron-deficient polyfluoroarenes is described. The protocol provides a useful and operationally simple access to a broad scope of alkylated polyfluoroarene derivatives in moderate to excellent yields. This also represents the first example of the introduction of a polyfluoroarene structure involving an alkylpalladium­(II) intermediate

    Palladium-Catalyzed Intramolecular Dearomatization of Indoles via Decarboxylative Alkynyl Termination

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    A highly diastereoselective dearomatization of indoles via palladium-catalyzed decarboxylative alkynyl termination was developed. This protocol provides dissimilar tetracyclic and tetrasubstituted indoline scaffolds bearing congested stereocenters, which led to operationally simple conditions, short time, and broad substrate scope. Additionally, this reaction system could be scaled to gram quantities in a satisfactory yield and diastereoselectivity

    Palladium-Catalyzed Domino Heck/Intermolecular C–H Bond Functionalization: Efficient Synthesis of Alkylated Polyfluoroarene Derivatives

    No full text
    An efficient palladium-catalyzed alkylation of electron-deficient polyfluoroarenes is described. The protocol provides a useful and operationally simple access to a broad scope of alkylated polyfluoroarene derivatives in moderate to excellent yields. This also represents the first example of the introduction of a polyfluoroarene structure involving an alkylpalladium­(II) intermediate

    Palladium-Catalyzed Radical Cascade Iododifluoromethylation/Cyclization of 1,6-Enynes with Ethyl Difluoroiodoacetate

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    A novel and convenient Pd-catalyzed radical cascade iododifluoromethylation/cyclization of 1,6-enynes with ethyl difluoroiodoacetate is demonstrated. The proposed transformation presents high stereoselectivity under mild and facile reaction conditions, thereby allowing an efficient access to a variety of iodine-containing difluoromethylated pyrrolidines. A possible radical pathway for the transformation is proposed on the basis of the results of control experiments and relevant literature reviews

    Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols with Hydroxylamine Hydrochloride To Give α,β-Unsaturated Amides and Alkenyl Nitriles

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    We have developed a highly selective method for the synthesis of α,β-unsaturated amides and alkenyl nitriles from readily available propargylic alcohols. The reaction proceeded smoothly under the neutral conditions with hydroxylamine hydrochloride (NH<sub>2</sub>OH·HCl) as the nitrogen source. The development of these new strategies has significantly extended the application of hydroxylamine hydrochloride to the chemistry of propargylic alcohols. Moreover, both secondary and tertiary alcohols have been highly regioselectively transformed to the desired products with good functional group compatibility

    Silver-Catalyzed Oxidative Cyclization of Propargylamide-Substituted Indoles: Synthesis of Phosphorated Indoloazepinones Derivatives

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    A silver-catalyzed oxidative cyclization of 2- or 3-propargylamide-substituted indoles to synthesize phosphorated indoloaze­pinone derivatives is described. This reaction displays a difunctionalizalion of alkynes with diphenyl­phosphine oxides to construct a seven-membered ring through a radical cyclization process. The indolo­azepinones derivatives are common structural motifs found in many natural products and pharmaceuticals

    Facile Synthesis of Disubstituted Isoxazoles from Homopropargylic Alcohol via Cî—»N Bond Formation

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    A novel iron-catalyzed aerobic oxidative reaction to synthesize disubstituted isoxazoles from homopropargylic alcohol, <i>t</i>-BuONO, and H<sub>2</sub>O is developed. The method provides mild conditions to afford a variety of useful substituted heterocycles in an efficient and regioselective manner. The mechanism has been studied and proposed, which indicates that the transformation can be realized through construction of a CN bond and CO bond, C–H oxidation, and then cyclization. Moreover, this method can be enlarged to gram scale
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