Iodine Catalysis for C(sp<sup>3</sup>)–H Fluorination with a Nucleophilic Fluorine Source
Daniel Bafaluy, Zoritsa Georgieva, Kilian Muñiz
Abstract
Iodine catalysis was developed for aliphatic fluorination through light-promoted homolytic C-H bond cleavage. The intermediary formation of amidyl radicals enables selective C-H functionalization via carbon-centered radicals. For the subsequent C-F bond formation, previous methods have typically been limited by a requirement for electrophilic fluorine reagents. We here demonstrate that the intermediary instalment of a carbon-iodine bond sets the stage for an umpolung, thereby establishing an unprecedented nucleophilic fluorination pathway.
Topics & Concepts
UmpolungNucleophileElectrophileBond cleavageChemistryHomolysisFluorineRadicalCatalysisReagentElectrophilic fluorinationMedicinal chemistryIodinePhotochemistryOrganic chemistryCombinatorial chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsRadical Photochemical Reactions