14 research outputs found

    Ethyl lactate mediated thioacetalization of aldehydes at ambient temperature

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    <p>Dithioacetalization reactions of aldehydes with thiols/thiophenols have been successfully achieved at room temperature by employing the green, bio-based ethyl lactate as the reaction medium. By means of this sustainable approach, a class of dithioacetals has been acquired with high diversity and efficiency.</p

    A Metal- and Azide-Free Multicomponent Assembly toward Regioselective Construction of 1,5-Disubstituted 1,2,3-Triazoles

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    The construction of 1,5-disubstituted 1,2,3-triazoles has been effected through the cascade dual C–N bond formation, N–N bond formation and an acyl migration-based C–C bond formation via the three-component reactions of enaminones, tosylhydrazine and primary amines. This metal- and azide-free, regioselective synthetic method proceeds in the presence of only molecular iodine

    Multicomponent Synthesis of Diverse <i>o</i>‑Arylated Benzamides via <i>o</i>‑Aminophenol (OAP) Directed C(sp<sup>2</sup>)‑H Arylation

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    <i>o</i>-Aminophenol (OAP) has been discovered as practical precursor of directing group (DG) in the palladium-catalyzed aromatic C–H arylation of benzamides. This newly identified, simple, and low cost DG has exhibited broad substrate tolerance in the rapid synthesis of various <i>o</i>-arylated benzamides via direct assemblies of benzoyl chlorides, aryl iodides, and different <i>o</i>-aminophenols in the form of step economical multicomponent reaction

    Domino Reactions Involving the Branched C–N and CC Cleavage of Enaminones Toward Pyridines Synthesis

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    The copper-catalyzed cascade reactions of enaminones and ammonium chloride have led to the unprecedented synthesis of 4-unsubstituted pyridines of both symmetrical and unsymmetrical structures. Under the aerobic copper-catalyzed conditions, the branched transformations of enaminones with C–N and CC bond cleavage provide the C2-C3/C5-C6 and C4 building blocks to construct the pyridine ring, respectively. The CC cleavage that provides the C4 atom in the pyridine product is the first example showing the reactivity of an enaminone as the donor of one carbon synthon

    Base-Promoted Synthesis of <i>N</i>‑Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

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    The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various <i>N</i>-substituted 1,2,3-triazoles by employing <i>t</i>-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance

    Copper-Catalyzed, C–C Coupling-Based One-Pot Tandem Reactions for the Synthesis of Benzofurans Using <i>o</i>‑Iodophenols, Acyl Chlorides, and Phosphorus Ylides

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    One-pot reactions involving acyl chlorides, phosphorus ylides, and <i>o</i>-iodophenols with copper catalysis have been established for the rapid synthesis of functionalized benzofurans. With all of these easily available and stable reactants, the construction of the target products has been accomplished via tandem transformations involving a key C–C coupling, leading to the formation of one C­(sp<sup>2</sup>)–C bond, one C­(sp<sup>2</sup>)–O bond, and one CC bond

    Base-Promoted Synthesis of <i>N</i>‑Substituted 1,2,3-Triazoles via Enaminone–Azide Cycloaddition Involving Regitz Diazo Transfer

    No full text
    The domino reactions between NH-based secondary enaminones and tosyl azide have been developed for the synthesis of various <i>N</i>-substituted 1,2,3-triazoles by employing <i>t</i>-BuONa as the base promoter. Through a key Regitz diazo-transfer process with tosyl azide, the reactions proceed efficiently at room temperature with good substrate tolerance

    Domino Reactions Involving the Branched C–N and CC Cleavage of Enaminones Toward Pyridines Synthesis

    No full text
    The copper-catalyzed cascade reactions of enaminones and ammonium chloride have led to the unprecedented synthesis of 4-unsubstituted pyridines of both symmetrical and unsymmetrical structures. Under the aerobic copper-catalyzed conditions, the branched transformations of enaminones with C–N and CC bond cleavage provide the C2-C3/C5-C6 and C4 building blocks to construct the pyridine ring, respectively. The CC cleavage that provides the C4 atom in the pyridine product is the first example showing the reactivity of an enaminone as the donor of one carbon synthon

    Stereoselective Synthesis of Indolyl‑<i>C</i>‑glycosides Enabled by Sequential Aminopalladation and Heck Glycosylation of 2‑Alkynylanilines with Glycals

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    An efficient and general approach for the synthesis of indolyl-C-glycosides via aminopalladation and subsequent Heck-type glycosylation of easily available 2-alkynylanilines and glycals has been developed. This protocol features excellent stereoselectivity, a broad substrate scope, and mild reaction conditions. In addition, 2,3-pseudoglycals also successfully participated in this cascade reaction, affording C2/C3-branched indolyl glycosides with high regio-/stereoselectivity. The utility of this protocol was also demonstrated by a large-scale reaction and diversified synthetic transformations of the desired products

    Tunable Synthesis of Disulfide-Functionalized Enaminones and 1,4-Thiazines via the Reactions of Enaminones and β‑Aminoethanethiol

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    The reactions of β-aminoethanethiol with <i>N</i>,<i>N</i>-dimethyl enaminones are performed to selectively provide disulfide-functionalized enaminones and 1,4-thiazines. By performing the reaction in water and catalyst-free conditions, the transamination and oxidative S–S coupling between the two substrates take place to give disulfide-functionalized enaminones. On the other hand, by using identical starting materials, the employment of the CuI catalyst in dimethyl sulfoxide enables the selective generation of 1,4-thiazines via tandem transamination and C­(sp<sup>2</sup>)–H bond thiolation
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