Exploiting Transient Radical Cations as Brønsted Acids for Allylic C–H Heteroarylation of Enol Silyl Ethers
Tsubasa Nakashima, Haruka Fujimori, Kohsuke Ohmatsu, Takashi Ooi
Abstract
Intermediary radical cations, generated through single-electron oxidation of enol silyl ethers by excited Ir-based photocatalysts, can be exploited as Brønsted acids for the activation of heteroarylcyanides. This strategy enables the direct allylic C-H heteroarylation of enol silyl ethers under visible-light irradiation.
Topics & Concepts
EnolSilylationAllylic rearrangementChemistryPhotochemistryExcited stateBrønsted–Lowry acid–base theoryMedicinal chemistryCatalysisOrganic chemistryPhysicsAtomic physicsCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsOxidative Organic Chemistry Reactions