“…Over the past few decades,agreat number of fluorinating and fluoroalkylating agents have been successfully developed, enabling facile synthesis of different kinds of fluorinecontaining molecules, [6] whereas the general approaches to access each fluoroalkylating building blocks typically require multistep syntheses.While such fluoroalkylating agents could only work in specific fluoroalkylation reactions,the development of efficient fluoroalkylation reactions,w hich are compatible with ab road array of fluorine-containing functional groups,w ill evidently offer ap erfect tactic for batch production of fluorinated products in medicinal chemistry. As part of our continuous efforts on nickel-catalyzed fluoroalkylation, [7] we envisioned that the addition of various in situ generated radicals from fluoroalkyl halides [6d] to 1,3enynes [8] would give allenyl radicals for nickel-catalyzed cross-coupling, [9] affording the allenes with structurally different fluorine-containing groups.I ndeed, such ar adical relay strategy was first used for 1,2-carbofluoroalkylation of alkenes by the group of Zhang,a nd then further illustrated by the group of Chu (Scheme 1). [10] However,a lkenes with chelating groups were essential for both transformations, possibly because of the unique catalytic reactivity of the nickel complex.…”