Articles producció científica> Química Analítica i Química Orgànica

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

  • Dades identificatives

    Identificador: imarina:6040630
    Autors:
    Mestre JLishchynskyi ACastillón SBoutureira O
    Resum:
    © 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.
  • Altres:

    Autor segons l'article: Mestre J; Lishchynskyi A; Castillón S; Boutureira O
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Boutureira Martín, Omar / Castillón Miranda, Sergio
    Paraules clau: Reagent Late-stage fluorination Heteroaromatic-compounds Glycals Efficient trifluoromethylation Direct cupration Copper-catalyzed trifluoromethylation Convenient route C-h trifluoromethylation Aryl boronic acids
    Resum: © 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.
    Àrees temàtiques: 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
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: omar.boutureira@urv.cat sergio.castillon@urv.cat
    Identificador de l'autor: 0000-0002-0768-8309 0000-0002-0690-7549
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/acceptedVersion
    Enllaç font original: https://pubs.acs.org/doi/abs/10.1021/acs.joc.8b00927
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Journal Of Organic Chemistry. 83 (15): 8150-8160
    Referència 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 de l'article: 10.1021/acs.joc.8b00927
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2018
    Tipus de publicació: Journal Publications
  • Paraules clau:

    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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