Palladium-catalyzed cross coupling reactions are invaluable to the synthesis of pharmaceuticals, materials, and other chemicals. However, when the reactants contain two or more halides or pseudohalides with comparable reactivities, controlling site selectivity can be challenging. We have shown that two different N-heterocyclic carbene (NHC) ligands provide orthogonal selectivity for reaction of aryl chlorides or triflates during Suzuki-Miyaura cross coupling. The NHC-controlled selectivity is general to diverse substrate substitution patterns and boronic acid coupling partners. Based on combined computational and experimental studies, the mechanism of ligand-controlled selectivity in these systems appears to have a novel origin. The extension of these results to controlling site selectivity during cross coupling of dihalogenated substrates is also described.

Using N-heterocyclic carbene ligands to control cross coupling selectivity

2019 Spring National Meeting

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