Fe-Mediated Hydrofluorination of Piperidines: Access towards Fluorinated Iminosugars

Late-stage hydrofluorination provides access to fluorinated bioactive compounds suitable for 19 F NMR monitoring of biological processes. We report Fe(III)-mediated radical hydrofluorination of highly substituted, chiral N -heterocycles containing piperidine, indolizidine and pyrrolidine scaffolds to the Markovnikov products. This method tolerated steric bulky substrates as well as substituents on nitrogen with different electronic effects. Finally, an Fe(III) catalytic system was compared with Co(II) and Ni(II) catalysts.