Palladium-Catalyzed Base-Free Suzuki–Miyaura Coupling Reactions of Fluorinated Alkenes and Arenes via a Palladium Fluoride Key Intermediate



A new strategy for C–C bond formation with organoboronates through C–F activation of fluorinated alkenes and arenes was developed. In this Pd-catalyzed Suzuki–Miyaura-type cross-coupling reaction, neither a base for enhancing the reactivity of the organoboron reagents nor a Lewis acid for promoting C–F bond activation was required. A fluoropalladium intermediate played an essential role in this reaction. In addition, a Ni(NHC) catalyst was efficient for C–C coupling through C–F bond activation of fluoroarenes.