Alkenyl Fluorosulfates-Expedient Partners for Palladium-Catalyzed Cross-Coupling Reactions

Alkenyl fluorosulfates are evaluated as the partners of palladium-catalyzed cross-coupling reactions and an alternative to more common triflates and halides. Efficient protocols for the multigram synthesis of title reactants using the reaction of carbonyl compounds with SO₂F₂ were documented. Reactivity of alkenyl fluorosulfates in Suzuki, Sonogashira, Heck, Stille, and Buchwald-Hartwig reactions, as well as Miyaura borylation under typical conditions, was studied, and limitations of the methods were established. It was found that alkenyl flurosulfates have similar or even higher reactivity in the cross-coupling reactions as compared to alkenyl triflates.