Substituted potassium internal vinyltrifluoroborates: preparation and use in Suzuki–Miyaura cross-coupling reactions

A collection of substituted potassium internal vinyltrifluoroborates was prepared and utilized in palladium-catalyzed cross-coupling reactions with aryl and heteroaryl halides. The cross-coupling reactions proceeded readily with Pd(PPh3)4 as a catalyst in toluene/H2O under reflux in the presence of Cs2CO3. The process is regiospecific with regard to the internal vinyltrifluoroborate starting material and tolerates a variety of functional groups. This unique collection of substituted internal vinyltrifluoroborates can be readily utilized in research pharmaceutical applications.