Pd-Catalyzed Suzuki-Type Cross-Coupling of 2-Pyridyl Carbamoyl Fluorides

Abstract

We describe a palladium-catalyzed Suzuki-type cross-coupling reaction of 2-pyridyl carbamoyl fluorides with boronic acids. 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. The developed method provides entry to medicinally relevant 2-pyridyl amides and tertiary aminopyridines following a reduction.