A new approach for the conversion of aryl ammonium salts to aryl-SiR3 or aryl-H products is herein reported. The method displays exceptional ligand-controlled selectivity for either pathway using N-heterocyclic carbene ligands and earth-abundant nickel as a catalyst. Reaction conditions are mild, capable of providing the desired product at ambient temperature, and produces trimethylamine as the sole byproduct. This method provides access to benzene derivatives and stable, non-toxic aryl silanes that are useful in a number of reactions, including cross couplings, oxidation to phenols, and halogenations, from simple aniline building blocks.

Ligand-controlled silylation and reduction of aryl ammonium salts using nickel N-heterocyclic carbene catalysis

253rd National Meeting (2017)

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