A palladium-catalyzed cross-coupling of gem-difluorinated cyclopropanes with boronic acids, providing the corresponding arylated/alkenylated/alkylated 2-fluoroallylic scaffolds, is generated. This new approach has good functional group compatibility for both gem-difluorinated cyclopropanes and boronic acids; thus, an array of synthetic building blocks of monofluoroalkene scaffolds including conjugated fluorodiene and skipped fluorodiene gave good yields with high Z-selectivity. Moreover, proficient application was described for monofluoroalkene, whereas the corresponding alkyl fluoride was constructed through hydrogenation.