Palladium - Catalyzed Cross - Coupling of Perfluoroalkenylzinc Reagents with Aryl Iodides. A New, Simple Synthesis of α,β,β-Trifluorostyrenes and the Stereoselective Preparation of 1-Arylperfluoroprepanes

Article abstract of DOI:10.1021/jo00247a010

Perfluoroalkenylzinc reagents coupled with aryl iodides in the presence of Pd(PPh3)4 (1-3 molpercent) to give the corresponding arylalkenes.A series of substituted α,β,β-trifluorostyrenes were prepared in good yields.This method provides ready availability of these fluorinated styrenes, which were previously obtained with difficulty.For the first time, 1-arylperfluoropropenes were prepared stereoselectively.Palladium-catalyzed reactions of 2 with aryl iodides gave stereospecific (E)-1-arylperfluoropropenes, and the same procedure with 3 gave stereoselective Z/E ratios ranging from 98/2 to 92/8.