53 research outputs found

    Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp<sup>2</sup>)–H, C(sp<sup>3</sup>)–H, and Late-Stage Functionalizations

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    Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C­(sp<sup>2</sup>)–H bonds of (hetero)­arenes and alkenes, as well as unactivated C­(sp<sup>3</sup>)–H bonds under Rh<sup>III</sup> catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope (not limited to strongly heterocyclic coordinating groups), and tolerance of valuable functional substituents, such as unprotected amine and hydroxyl groups. The synthetic applicability of this protocol is also demonstrated by late-stage functionalization of biologically important scaffolds

    Expedient Synthesis of Pyrroloquinolinones by Rh-Catalyzed Annulation of <i>N</i>‑Carbamoyl Indolines with Alkynes through a Directed C–H Functionalization/C–N Cleavage Sequence

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    A Rh-catalyzed redox-neutral C–H functionalization of <i>N</i>-carbamoyl indolines with various internal alkynes has been developed. The reaction, which involves the sequential cleavage of the C–H bond of the indoline at the C7-position and the C–N bond of the urea motif, provides a divergent protocol to rapidly assemble fused-ring pyrrolo­quinolinone analogues by using a direct alkenylation/annulation strategy with high efficiency and selectivity

    Chelation-Assisted Rhodium-Catalyzed Direct Amidation with Amidobenziodoxolones: C(sp<sup>2</sup>)–H, C(sp<sup>3</sup>)–H, and Late-Stage Functionalizations

    No full text
    Air-stable and convenient amidobenziodoxolones as an amidating reagent were disclosed to enable direct amidation on a wide range of C­(sp<sup>2</sup>)–H bonds of (hetero)­arenes and alkenes, as well as unactivated C­(sp<sup>3</sup>)–H bonds under Rh<sup>III</sup> catalysis. The approach to access 49 examples of structurally diverse amides is featured by mild conditions, complete chemoselectivity and regioselectivity, broad substrate scope (not limited to strongly heterocyclic coordinating groups), and tolerance of valuable functional substituents, such as unprotected amine and hydroxyl groups. The synthetic applicability of this protocol is also demonstrated by late-stage functionalization of biologically important scaffolds

    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation

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    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylatio

    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation

    No full text
    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylatio

    Desymmetrization of Bicyclo[3.<i>n</i>.1]-3-one Derivatives by Palladium-Catalyzed Asymmetric Allylic Alkylation

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    Desymmetrization of carbon nucleophiles by palladium-catalyzed asymmetric allylic alkylation has been realized for the first time. Products with three chiral centers were obtained in good yield and with high diastereo- and enantioselectivity. The method offers an efficient access to optically active tropane derivatives

    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylation

    No full text
    Kinetic Resolution of 2,3-Dihydro-2-substituted 4-Quinolones by Palladium-Catalyzed Asymmetric Allylic Alkylatio

    Stereo- and Chemoselective Cross-Coupling between Two Electron-Deficient Acrylates: An Efficient Route to (<i>Z</i>,<i>E</i>)‑Muconate Derivatives

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    A Ru-catalyzed direct oxidative cross-coupling reaction of acrylates was developed. It offers a straightforward and atom-economical protocol for the synthesis of functionalized (<i>Z</i>,<i>E</i>)-muconate derivatives in moderate to good yields with good stereo- and chemoselectivities. The conjugated muconates bearing differentiable terminal functionality can be selectively transformed into versatile synthetic intermediates widely used in organic synthesis
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