Synthesis of gem-difluorocyclopentane/hexane building blocks

Synthesis of gem-difluorocycloalkane building blocks is described. [Display omitted] •An approach to gem-difluorocyclopentane/hexane carboxylic acids and amines is developed.•Straightforward fluorination of 3-ketocycloalkanecarboxylates leads to the target 3,3-difluoro-substitited cycloalkanes.•For the 2,2-difluorocycloalkanecarboxylic acids, the bypass route via (2-oxocycloalkyl)methyl acetates is necessary.•2,2-Difluorocycloalkylamines can be obtained via deoxofluorination of 2-(trifluoroacetylamino)cycloalkanones. An approach to the preparation of gem-difluorocyclopentane/hexane-derived carboxylic acids and amines is described. Whereas for 3,3-difluoro-substituted cycloalkanones, straightforward deoxofluorination of the corresponding ketoesters led to the target compounds, in the case of 2,2-difluoro isomers, the bypass or alternative routes were necessary.