The regioselective synthesis of fluorinated allenes via a metal-free 1,4-fluoroamination of 1,3-enynes is presented. This method employs commercially available N-fluorobenzenesulfonimide serving as both the nitrogen source and the fluorine source, affording access to various tetrasubstituted allenes in a straightforward and atom-economic pathway. Preliminary mechanistic studies and theoretical studies revealed that this reaction might undergo an intimate ion-pair mechanism.