Bisphosphine/Nickel-Catalyzed C-O Cross-Coupling of Phenols with Chloropyridine and Related Electrophiles.

Notwithstanding recent developments in nickel-catalyzed C-O cross-coupling chemistry, such transformations of substituted phenols and (hetero)aryl chlorides with a useful reaction scope have yet to be reported. In this work, we disclose the results of catalyst screening that allowed the identification of PhPAd-DalPhos/NiCOD2 as an effective catalyst system under thermal conditions for the O-arylation of substituted phenols with chloropyridine-type electrophiles, leading to pyridyl-O-aryl frameworks that are found in active pharmaceutical ingredients.