Herein we reported nickel-catalyzed cross-coupling of gem-difluorinated cyclopropanes with boronic acids, providing the corresponding ary-lated 2-fluoroallylic scaffolds. This approach uses commercially available phosphine ligand Xantphos to obtain monofluorinated alkenes with high regioselectivity and Z-stereoselectivity. Mechanistic studies proposed Ni(II)-fluoroallyl pathway and exclude the radical pathway. Meanwhile, DFT study of the reductive elimination clarifies the origin of the high linear selectivity.