The preparation of a new series of dinuclear zinc reagents is reported (eqs 1 and 2).Unlike α, ω-difunctionalized perfluoroalkyl di-Grignard reagents, which have a half-life of only two hours at-50 ℃ in THF, we observed that 87 ％ of the dizinc reagents remained in acetonitrile solution after 300 h at room temperature.We demonstrate that the reagents can be used to prepare novel fluoroorganics containing either perfluoroalkyl ring systems or perfluoroalkyl linked arenes under relatively mild conditions (eqs 3 and 4).We also show that these zinc reagents can be used to transmetalate nickel to form monocuclear metallacycles.Different reaction conditions are needed for different chain lengths because in some instances the perfluoroalkylations are competitive with unusual dicuprate formation.We also present results demonstrating that perfluoroalkyl-based metallacycles are exceptionally effective at stabilizing high valent metal complexes.