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Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas

  • Datos identificativos

    Identificador: imarina:9326625
    Autores:
    Medina-Gil, TSadurní, AHammarback, LAEchavarren, AM
    Resumen:
    Acetylene gas isan important feedstock for chemical production,although it is underutilized in organic synthesis. We have developedan intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanesby a stereospecific aryloxycyclization through the nucleophilic regioselectiveopening of cyclopropyl gold(I)-carbene intermediates. The syntheticapplication of this method was demonstrated in the late-stage functionalizationof the natural product lapachol.
  • Otros:

    Autor según el artículo: Medina-Gil, T; Sadurní, A; Hammarback, LA; Echavarren, AM
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: ECHAVARREN PABLOS, ANTONIO / Sadurní Parera, Anna
    Palabras clave: Gold catalysis Enantioselectivecatalysis Chromanes Aryloxycyclization Alkynes Alkenes Acetylene 2+2 cycloaddition
    Resumen: Acetylene gas isan important feedstock for chemical production,although it is underutilized in organic synthesis. We have developedan intermolecular gold(I)-catalyzed alkyne/alkene reaction of o-allylphenols with acetylene gas that gives rise to chromanesby a stereospecific aryloxycyclization through the nucleophilic regioselectiveopening of cyclopropyl gold(I)-carbene intermediates. The syntheticapplication of this method was demonstrated in the late-stage functionalizationof the natural product lapachol.
    Áreas temáticas: Química Materiais Interdisciplinar General chemistry Engenharias ii Ciências agrárias i Chemistry, physical Chemistry (miscellaneous) Chemistry (all) Catalysis Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: anna.sadurni@urv.cat antoniomaria.echavarren@urv.cat
    Identificador del autor: 0000-0002-6418-7930
    Fecha de alta del registro: 2024-08-03
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/10.1021/acscatal.3c02461
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Acs Catalysis. 13 (16): 10751-10755
    Referencia de l'ítem segons les normes APA: Medina-Gil, T; Sadurní, A; Hammarback, LA; Echavarren, AM (2023). Gold(I)-Catalyzed Intermolecular Aryloxyvinylation with Acetylene Gas. Acs Catalysis, 13(16), 10751-10755. DOI: 10.1021/acscatal.3c02461
    DOI del artículo: 10.1021/acscatal.3c02461
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2023
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Catalysis,Chemistry (Miscellaneous),Chemistry, Physical
    Gold catalysis
    Enantioselectivecatalysis
    Chromanes
    Aryloxycyclization
    Alkynes
    Alkenes
    Acetylene
    2+2 cycloaddition
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Engenharias ii
    Ciências agrárias i
    Chemistry, physical
    Chemistry (miscellaneous)
    Chemistry (all)
    Catalysis
    Astronomia / física
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