Organophotochemical S<sub>N</sub>Ar Reactions of Mildly Electron‐Poor Fluoroarenes
Thomas Sheridan, Hatice G. Yayla, Yajing Lian, Julien Genovino, Nat Monck, Jonathan W. Burton
Abstract
C–F functionalization of arenes with a range of alcohol and pyrazole nucleophiles has been achieved without the need for metal catalysts or highly electron‐poor substrates. Treatment of fluoroarenes with alcohols or pyrazoles and DDQ under irradiation by blue LED light provides the corresponding substituted products. The procedure is complementary to classical S N Ar chemistry which generally requires basic reaction conditions and high temperatures, and provides products under non‐basic conditions at ≈ 40 °C.
Topics & Concepts
ChemistryNucleophileCatalysisPhotochemistryPyrazoleSurface modificationAlcoholIrradiationCombinatorial chemistryMedicinal chemistryOrganic chemistryPhysical chemistryNuclear physicsPhysicsFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods