Deconstructive functionalizations involving scission of carbon-carbon double bonds are well established. In contrast, unstrained C(sp(3))-C(sp(3)) bond cleavage and functionalization have less precedent. Here we report the use of deconstructive fluorination to access mono-and difluorinated amine derivatives by C(sp(3))-C(sp(3)) bond cleavage in saturated nitrogen heterocycles such as piperidines and pyrrolidines. Silver-mediated ring-opening fluorination using Selectfluor highlights a strategy for cyclic amine functionalization and late-stage skeletal diversification, establishing cyclic amines as synthons for amino alkyl radicals and providing synthetic routes to valuable building blocks.