Articles producció científica> Química Analítica i Química Orgànica

Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived ligandless CuCF3

  • Datos identificativos

    Identificador: imarina:6040630
    Autores:
    Mestre JLishchynskyi ACastillón SBoutureira O
    Resumen:
    © 2018 American Chemical Society. We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)-I bond using fluoroform-derived ligandless CuCF3. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting products enabled the controlled, late-stage synthesis of single regioisomers of complex CF3-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.
  • Otros:

    Autor según el artículo: Mestre J; Lishchynskyi A; Castillón S; Boutureira O
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio
    Palabras clave: Reagent Late-stage fluorination Heteroaromatic-compounds Glycals Efficient trifluoromethylation Direct cupration Copper-catalyzed trifluoromethylation Convenient route C-h trifluoromethylation Aryl boronic acids
    Resumen: © 2018 American Chemical Society. We herein present a flexible approach for the incorporation of CF3 units into a predefined site of electron-rich alkenes that exploits the regiocontrolled introduction of an iodine handle and subsequent trifluoromethylation of the C(sp2)-I bond using fluoroform-derived ligandless CuCF3. The broad substrate scope and functional group tolerance together with the scalability and purity of the resulting products enabled the controlled, late-stage synthesis of single regioisomers of complex CF3-scaffolds, such as sugars, nucleosides (antivirals), and heterocycles (indoles and chromones), with potential for academic and industrial applications.
    Áreas temáticas: Química Organic chemistry Odontología Medicina ii Medicina i Materiais Interdisciplinar General medicine Farmacia Ensino Engenharias iv Engenharias ii Engenharias i Ciências biológicas iii Ciências biológicas ii Ciências biológicas i Ciências agrárias i Ciência de alimentos Chemistry, organic Biotecnología Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: omar.boutureira@urv.cat sergio.castillon@urv.cat
    Identificador del autor: 0000-0002-0768-8309 0000-0002-0690-7549
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/acceptedVersion
    Enlace a la fuente original: https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b00927
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Journal Of Organic Chemistry. 83 (15): 8150-8160
    Referencia de l'ítem segons les normes APA: Mestre J; Lishchynskyi A; Castillón S; Boutureira O (2018). Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived ligandless CuCF3. Journal Of Organic Chemistry, 83(15), 8150-8160. DOI: 10.1021/acs.joc.8b00927
    DOI del artículo: 10.1021/acs.joc.8b00927
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2018
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Chemistry, Organic,Organic Chemistry
    Reagent
    Late-stage fluorination
    Heteroaromatic-compounds
    Glycals
    Efficient trifluoromethylation
    Direct cupration
    Copper-catalyzed trifluoromethylation
    Convenient route
    C-h trifluoromethylation
    Aryl boronic acids
    Química
    Organic chemistry
    Odontología
    Medicina ii
    Medicina i
    Materiais
    Interdisciplinar
    General medicine
    Farmacia
    Ensino
    Engenharias iv
    Engenharias ii
    Engenharias i
    Ciências biológicas iii
    Ciências biológicas ii
    Ciências biológicas i
    Ciências agrárias i
    Ciência de alimentos
    Chemistry, organic
    Biotecnología
    Astronomia / física
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