The perfluoroallylation of alkynes and transformation of the products

The addition of perfluoroallyl iodide to alkynes 1 initiated by AIBN in the absence of solvent 65 °C gave the corresponding 1:1 adducts (1,1,2,3,3-pentafluoro-5-iodopenta-1,4-dienes) 2. The reaction of 2 with boronic acids 3 and terminal alkynes 1 in the presence of catalytic palladium afforded the cross-coupling products 4 and 5, respectively.