Visible-Light-Mediated C–H Alkylation of Pyridine Derivatives
Fatima Rammal, Di Gao, Sondes Boujnah, Annie−Claude Gaumont, Aqeel A. Hussein, Sami Lakhdar
Abstract
We report herein a visible-light-mediated C–H alkylation of pyridine derivatives that proceeds by simple combination of a large variety of N-alkoxypyridinium ions with alkanes in the presence of 2 mol % of fac-Ir(ppy)3 under blue illumination. The mild reaction conditions together with the high group functional tolerance make of this process a useful synthetic platform for the construction of structurally strained heterocycles. Detailed mechanistic investigations, including density functional theory calculations and quantum yield measurement, allowed us to understand factors controlling the reactivity and the selectivity of the reaction.
Topics & Concepts
ChemistryAlkylationPyridineQuantum yieldReactivity (psychology)Yield (engineering)Density functional theorySelectivityPhotochemistryFunctional groupCombinatorial chemistryVisible spectrumReaction conditionsIonComputational chemistryOrganic chemistryCatalysisFluorescencePathologyPolymerAlternative medicineOptoelectronicsMaterials scienceMetallurgyMedicineQuantum mechanicsPhysicsRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions