Articles producció científica> Química Analítica i Química Orgànica

Switchable photocatalysis for the chemodivergent benzylation of 4-cyanopyridines

  • Dades identificatives

    Identificador: imarina:9267367
    Autors:
    Georgiou ESpinnato DChen KMelchiorre P
    Resum:
    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.
  • Altres:

    Autor segons l'article: Georgiou E; Spinnato D; Chen K; Melchiorre P
    Departament: Química Analítica i Química Orgànica
    Autor/s de la URV: Georgiou, Eleni / Spinnato, Davide
    Paraules clau: Radicals Ketones Heterocycles Electron-transfer C-h functionalization Arylation Alkylation Activation
    Resum: 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.
    Àrees temàtiques: Química Materiais Interdisciplinar General chemistry Farmacia Ciências biológicas iii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Astronomia / física
    Accès a la llicència d'ús: https://creativecommons.org/licenses/by/3.0/es/
    Adreça de correu electrònic de l'autor: davide.spinnato@estudiants.urv.cat eleni.georgiou@estudiants.urv.cat
    Data d'alta del registre: 2024-09-07
    Versió de l'article dipositat: info:eu-repo/semantics/publishedVersion
    Enllaç font original: https://pubs.rsc.org/en/content/articlelanding/2022/sc/d2sc02698h
    URL Document de llicència: https://repositori.urv.cat/ca/proteccio-de-dades/
    Referència a l'article segons font original: Chemical Science. 13 (27): 8060-8064
    Referència 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 de l'article: 10.1039/d2sc02698h
    Entitat: Universitat Rovira i Virgili
    Any de publicació de la revista: 2022
    Tipus de publicació: Journal Publications
  • Paraules clau:

    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
  • Documents:

  • Cerca a google

    Search to google scholar