A palladium-catalyzed gem-difluoroallylation of propargyl sulfonates with gem-difluoroallylboron has been developed. The reaction features synthetic simplicity and high functional group tolerance, affording 3,3-difluoro-skipped 1,5-enynes with high efficiency and regioselectivity. In particular, the resulting products can serve as versatile synthons for diversified transformations, having potential applications in medicinal chemistry.