<i>α</i> ‐Fluoroalkenylzinc Halide: Preparation, Stability, Structures, and Application to Monofluoroalkene Synthesis

Monofluoroalkene synthesis using α ‐fluoroalkenylmetal species has remained a synthetic challenge due to their inherent instability. In this study, the generation, structural characterization, and synthetic applications of α ‐fluoroalkenylzinc halides for monofluoroalkene synthesis are reported. α ‐Fluoroalkenylzinc iodide can be prepared via the oxidative addition of 1‐fluoro‐1‐iodoalkenes to zinc at room temperature. These species exhibited remarkable thermal stability–no significant decomposition at room temperature. α ‐Fluoroalkenylzinc iodides readily underwent Negishi‐type cross‐couplings and copper‐mediated addition reactions, affording various monofluoroalkenes.