Chemo‐ and Site‐Selective Electro‐Oxidative Alkane Fluorination by C(sp<sup>3</sup>)−H Cleavage
Maximilian Stangier, Alexej Scheremetjew, Lutz Ackermann
Abstract
Abstract Electrochemical fluorinations of C(sp 3 )−H bonds with a nucleophilic fluoride source have been accomplished in a chemo‐ and site‐selective fashion, avoiding the use of electrophilic F + sources and stoichiometric oxidants. The introduced metal‐free strategy exhibits high functional group tolerance, setting the stage for late‐stage fluorinations of biorelevant motifs. The synthetic utility of the C(sp 3 )−H fluorination was reflected by subsequent one‐pot arylation of the generated benzylic fluorides.
Topics & Concepts
NucleophileElectrophileChemistryFluorideAlkaneOxidative cleavageElectrochemistryBond cleavageStoichiometryCleavage (geology)FluorineMedicinal chemistryCatalysisOrganic chemistryInorganic chemistryElectrodePhysical chemistryMaterials scienceFracture (geology)Composite materialFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods