75 research outputs found

    Correction to Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2‑Chloro‑<i>N</i>‑(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines

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    Correction to Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2‑Chloro‑<i>N</i>‑(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridine

    Versatile Enantioselective Synthesis of Functionalized Lactones via Copper-Catalyzed Radical Oxyfunctionalization of Alkenes

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    A versatile method for the rapid synthesis of diverse enantiomerically enriched lactones has been developed based on Cu-catalyzed enantioselective radical oxyfunctionalization of alkenes. The scope of this strategy encompasses a series of enantioselective difunctionalization reactions: oxyazidation, oxysulfonylation, oxyarylation, diacyloxylation, and oxyalkylation. These reactions provide straightforward access to a wide range of useful chiral lactone building blocks containing tetrasubstituted stereogenic centers, which are hard to access traditionally

    Ligand-Controlled Palladium-Catalyzed Regiodivergent Suzuki–Miyaura Cross-Coupling of Allylboronates and Aryl Halides

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    An orthogonal set of catalyst systems has been developed for the Suzuki–Miyaura coupling of 3,3-disubstituted and 3-monosubstituted allylboronates with (hetero)­aryl halides. These methods allow for the highly selective preparation of either the α- or the γ-isomeric coupling product

    Correction to Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2‑Chloro‑<i>N</i>‑(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridines

    No full text
    Correction to Synthesis of Heterocycles via Pd-Ligand Controlled Cyclization of 2‑Chloro‑<i>N</i>‑(2-vinyl)aniline: Preparation of Carbazoles, Indoles, Dibenzazepines, and Acridine

    Regioselective 2‑Amination of Polychloropyrimidines

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    The regioselective amination of substituted di- and trichloropyrimidines affording the 2-substituted products is reported. While aryl- and heteroarylamines require the use of a dialkylbiarylphosphine-derived palladium catalyst for high efficiency, more nucleophilic dialkylamines produce 2-aminopyrimidines under noncatalyzed S<sub>N</sub>Ar conditions. The key is the use of 5-trimethylsilyl-2,4-dichloropyrimidine as a surrogate for the parent dichloropyrimidine. For more challenging cases, the 2-chloro-4-thiomethoxy analogues were prepared and exclusively afford the desired 2-aminated-4-thiomethoxypyrimidine products

    Enantioselective CuH-Catalyzed Anti-Markovnikov Hydroamination of 1,1-Disubstituted Alkenes

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    Enantioselective synthesis of β-chiral amines has been achieved via copper-catalyzed hydro­amination of 1,1-disubstituted alkenes with hydroxylamine esters in the presence of a hydrosilane. This mild process affords a range of structurally diverse β-chiral amines, including β-deuterated amines, in excellent yields with high enantio­selectivities. Furthermore, catalyst loading as low as 0.4 mol% could be employed to deliver product in undiminished yield and selectivity, demonstrating the practicality of this method for large-scale synthesis

    Continuous-Flow Preparation and Use of β‑Chloro Enals Using the Vilsmeier Reagent

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    The Vilsmeier reagent is used in the preparation of a wide variety of heterocycles, such as pyrazoles, <i>via</i> formation of β-chloroacrolein intermediates. However, use of this extremely reactive reagent on large scale requires special precautions to avoid potentially dangerous exotherms. This article describes the safe preparation at room temperature of the Vilsmeier reagent under flow conditions for the formation of β-chloroacroleins and 3-formylchromones, as well as the use of these in multistep, continuous flow processes for the syntheses of β-acrylonitriles and polysubstituted pyrazoles

    Continuous-Flow Synthesis of Monoarylated Acetaldehydes Using Aryldiazonium Salts

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    Anilines and ethyl vinyl ether can be used as precursors for a process that is the synthetic equivalent of the α-arylation of acetaldehyde enolate. The reaction manifests a high level of functional group compatibility, allowing the ready preparation of a number of synthetically valuable compounds

    Palladium-Catalyzed Negishi Coupling of α‑CF<sub>3</sub> Oxiranyl Zincate: Access to Chiral CF<sub>3</sub>‑Substituted Benzylic Tertiary Alcohols

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    We report a Pd-catalyzed stereospecific α-arylation of optically pure 2,3-epoxy-1,1,1-trifluoropropane (TFPO). This method allows for the direct and reliable preparation of optically pure 2-CF<sub>3</sub>-2-(hetero)­aryloxiranes, which are precursors to many CF<sub>3</sub>-substituted tertiary alcohols. The use of continuous-flow methods has allowed the deprotonation of TFPO and subsequent zincation at higher temperature compared to that under traditional batch conditions

    Correction to Continuous-Flow Synthesis of Monoarylated Acetaldehydes Using Aryldiazonium Salts

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    Correction to Continuous-Flow Synthesis of Monoarylated Acetaldehydes Using Aryldiazonium Salt
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