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Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative 18 F-fluorodecarboxylation with [ 18 F]fluoride affording biologically relevant 18 F-difluoromethyl(ene)-containing molecules. This no-carrier added process provides a solution to a known challenge in radiochemistry and expands the radiochemical space available for positron emission tomography (PET) ligand discovery. Scalability on a fully automated radiosynthetic platform is exemplified with the production of [ 18 F]4,4-difluoropiperidine that, we demonstrate, is amenable to postlabeling functionalization including N -heteroarylation and amide as well as sulfonamide bond formation.