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

Abstract

A series of di- or trisubstituted alkenecontaining 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 5 mol% of tetrakis(triphenylphosphine) palladium(0) and 3.0 equiv. of cesium carbonate in aqueous 1,4-dioxane under microwave irradiation.