Rapid and Direct Photocatalytic C(sp<sup>3</sup>)−H Acylation and Arylation in Flow
Daniele Mazzarella, Antonio Pulcinella, Loïc Bovy, Rémy Broersma, Timothy Noël
Abstract
Abstract Herein, we report a photocatalytic procedure that enables the acylation/arylation of unfunctionalized alkyl derivatives in flow. The method exploits the ability of the decatungstate anion to act as a hydrogen atom abstractor and produce nucleophilic carbon‐centered radicals that are intercepted by a nickel catalyst to ultimately forge C(sp 3 )−C(sp 2 ) bonds. Owing to the intensified conditions in flow, the reaction time can be reduced from 12–48 hours to only 5–15 minutes. Finally, kinetic measurements highlight how the intensified conditions do not change the reaction mechanism but reliably speed up the overall process.
Topics & Concepts
PhotocatalysisAcylationChemistryNucleophileCatalysisRadicalPhotochemistryCarbon fibersAlkylFlow chemistryHydrogen atomHydrogen bondNickelHydrogenMedicinal chemistryOrganic chemistryMoleculeMaterials scienceComposite numberComposite materialRadical Photochemical ReactionsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions