Copper-Catalyzed C–H Fluorination/Functionalization Sequence Enabling Benzylic C–H Cross Coupling with Diverse Nucleophiles
Aristidis Vasilopoulos, Dung L. Golden, Joshua A. Buss, Shannon S. Stahl
Abstract
Site-selective transformation of benzylic C–H bonds into diverse functional groups is achieved via Cu-catalyzed C–H fluorination with N-fluorobenzenesulfonimide (NFSI), followed by substitution of the resulting fluoride with various nucleophiles. The benzyl fluorides generated in these reactions are reactive electrophiles in the presence of hydrogen-bond donors or Lewis acids, allowing them to be used without isolation in C–O, C–N, and C–C coupling reactions.
Topics & Concepts
ChemistryNucleophileElectrophileCatalysisSurface modificationMedicinal chemistryLewis acids and basesCombinatorial chemistryElectrophilic fluorinationFluorideFluorineHydrogen bondOrganic chemistryMoleculeInorganic chemistryPhysical chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsSynthesis and Catalytic Reactions