Potassium (E)-Alkenylaryltrifluoroborates: Orthogonal Functionalization of Haloaryltrifluoroborates via Heck-Mizoroki Reaction

Abstract

A series of di- or trisubstituted alkene-containing potassium organotrifluoroborates was prepared from the corresponding haloaryltrifluoroborates via palladium-catalyzed Heck-Mizoroki reaction with various olefins in good to excellent yields. Furthermore, the Suzuki-Miyaura cross-coupling reaction of these alkenylaryltrifluoroborates was successfully carried out with aryl and alkenyl bromides using 5mol% of tetrakis(triphenylphosphine)palladium(0) and 3.0equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.