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Switchable photocatalysis for the chemodivergent benzylation of 4-cyanopyridines

  • Datos identificativos

    Identificador: imarina:9267367
    Autores:
    Georgiou ESpinnato DChen KMelchiorre P
    Resumen:
    We report a photocatalytic strategy for the chemodivergent radical benzylation of 4-cyanopyridines. The chemistry uses a single photoredox catalyst to generate benzyl radicals upon N-F bond activation of 2-alkyl N-fluorobenzamides. The judicious choice of different photocatalyst quenchers allowed us to select at will between mechanistically divergent processes. The two reaction manifolds, an ipso-substitution path proceeding via radical coupling and a Minisci-type addition, enabled selective access to regioisomeric C4 or C2 benzylated pyridines, respectively. Mechanistic investigations shed light on the origin of the chemoselectivity switch.
  • Otros:

    Autor según el artículo: Georgiou E; Spinnato D; Chen K; Melchiorre P
    Departamento: Química Analítica i Química Orgànica
    Autor/es de la URV: Georgiou, Eleni / Spinnato, Davide
    Palabras clave: Radicals Ketones Heterocycles Electron-transfer C-h functionalization Arylation Alkylation Activation
    Resumen: We report a photocatalytic strategy for the chemodivergent radical benzylation of 4-cyanopyridines. The chemistry uses a single photoredox catalyst to generate benzyl radicals upon N-F bond activation of 2-alkyl N-fluorobenzamides. The judicious choice of different photocatalyst quenchers allowed us to select at will between mechanistically divergent processes. The two reaction manifolds, an ipso-substitution path proceeding via radical coupling and a Minisci-type addition, enabled selective access to regioisomeric C4 or C2 benzylated pyridines, respectively. Mechanistic investigations shed light on the origin of the chemoselectivity switch.
    Áreas temáticas: Química Materiais Interdisciplinar General chemistry Farmacia Ciências biológicas iii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Astronomia / física
    Acceso a la licencia de uso: https://creativecommons.org/licenses/by/3.0/es/
    Direcció de correo del autor: davide.spinnato@estudiants.urv.cat eleni.georgiou@estudiants.urv.cat
    Fecha de alta del registro: 2024-09-07
    Versión del articulo depositado: info:eu-repo/semantics/publishedVersion
    Enlace a la fuente original: https://pubs.rsc.org/en/content/articlelanding/2022/sc/d2sc02698h
    URL Documento de licencia: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referencia al articulo segun fuente origial: Chemical Science. 13 (27): 8060-8064
    Referencia de l'ítem segons les normes APA: Georgiou E; Spinnato D; Chen K; Melchiorre P (2022). Switchable photocatalysis for the chemodivergent benzylation of 4-cyanopyridines. Chemical Science, 13(27), 8060-8064. DOI: 10.1039/d2sc02698h
    DOI del artículo: 10.1039/d2sc02698h
    Entidad: Universitat Rovira i Virgili
    Año de publicación de la revista: 2022
    Tipo de publicación: Journal Publications
  • Palabras clave:

    Chemistry (Miscellaneous),Chemistry, Multidisciplinary
    Radicals
    Ketones
    Heterocycles
    Electron-transfer
    C-h functionalization
    Arylation
    Alkylation
    Activation
    Química
    Materiais
    Interdisciplinar
    General chemistry
    Farmacia
    Ciências biológicas iii
    Ciências biológicas i
    Chemistry, multidisciplinary
    Chemistry (miscellaneous)
    Chemistry (all)
    Astronomia / física
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