Pd-catalyzed Suzuki-type cross-coupling of 2-pyridyl carbamoyl fluorides

We describe a palladium-catalyzed Suzuki-type cross-coupling reaction of 2-pyridyl carbamoyl fluorides with boronic acids, which provides entry to medicinally relevant pyridyl amides. Mechanistic studies, including the synthesis and reactivity of carbamoyl Pd-F complexes, reveal the importance of both the fluoride electrophile and nitrogen directing group for aiding reactivity. A directing group strategy enables the Pd-catalyzed Suzuki-type cross-coupling of carbamoyl fluorides with boronic acids to yield medicinally relevant pyridyl amides.