Author, as appears in the article.: Georgiou E; Spinnato D; Chen K; Melchiorre P
Department: Química Analítica i Química Orgànica
URV's Author/s: Georgiou, Eleni / Spinnato, Davide
Keywords: Radicals Ketones Heterocycles Electron-transfer C-h functionalization Arylation Alkylation Activation
Abstract: 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.
Thematic Areas: Química Materiais Interdisciplinar General chemistry Farmacia Ciências biológicas iii Ciências biológicas i Chemistry, multidisciplinary Chemistry (miscellaneous) Chemistry (all) Astronomia / física
licence for use: https://creativecommons.org/licenses/by/3.0/es/
Author's mail: davide.spinnato@estudiants.urv.cat eleni.georgiou@estudiants.urv.cat
Record's date: 2024-09-07
Papper version: info:eu-repo/semantics/publishedVersion
Link to the original source: https://pubs.rsc.org/en/content/articlelanding/2022/sc/d2sc02698h
Licence document URL: https://repositori.urv.cat/ca/proteccio-de-dades/
Papper original source: Chemical Science. 13 (27): 8060-8064
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
Article's DOI: 10.1039/d2sc02698h
Entity: Universitat Rovira i Virgili
Journal publication year: 2022
Publication Type: Journal Publications
Repositori URV