F-Difluoromethyl(ene) Motifs via Oxidative Fluorodecarboxylation with [F]Fluoride.

Herein, we report that α-fluorocarboxylic acids undergo manganese-mediated oxidative F-fluorodecarboxylation with [F]fluoride affording biologically relevant 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 [F]4,4-difluoropiperidine that, we demonstrate, is amenable to postlabeling functionalization including -heteroarylation and amide as well as sulfonamide bond formation.