Transition‐Metal‐Free Coupling of Polyfluorinated Arenes and Functionalized, Masked Aryl Nucleophiles
Lucie Finck, Martin Oestreich
Abstract
Abstract A chemoselective C(sp 2 )−C(sp 2 ) coupling of sufficiently electron‐deficient fluorinated arenes and functionalized N ‐aryl‐ N’ ‐silyldiazenes as masked aryl nucleophiles is reported. The fluoride‐promoted transformation involves the in situ generation of the aryl nucleophile decorated with various sensitive functional groups followed by a stepwise nucleophilic aromatic substitution (S N Ar). These reactions typically proceed at room temperature within minutes. This catalytic process allows for the functionalization of both coupling partners, furnishing highly fluorinated biaryls in good yields.
Topics & Concepts
NucleophileArylChemistryFluorideNucleophilic aromatic substitutionCatalysisCombinatorial chemistryTransition metalSurface modificationCoupling (piping)PhotochemistryMedicinal chemistryNucleophilic substitutionOrganic chemistryInorganic chemistryMaterials sciencePhysical chemistryAlkylMetallurgyFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods