A nickel-catalyzed tandem alkoxylation/claisen rearrangement strategy for the oxy-difluoroallylation of ynamides has been developed. In this reaction, 3,3-difluoroallyl alcohol was used as a fluorine-containing building block to construct the C-CF2 bond for the first time. This approach is recognized for its robust tolerance of functional groups, impressive yields, and excellent atomic efficiency, all achieved under mild reaction conditions. A series of β,β-difluoromethyleneamide derivatives were efficiently obtained through simple operations, and their practicality was confirmed through gram-scale synthesis and product derivatization.