Nickel-Catalyzed Reaction of Arylzinc Reagents with N-Aromatic Heterocycles: A Straightforward Approach to C−H Bond Arylation of Electron-Deficient Heteroaromatic Compounds

The reaction of electron-deficient N-heteroaromatic compounds, such as pyridines and quinolines, with arylzinc reagents in the presence of a catalytic amount of a nickel complex affords the arylated products. The reaction is likely to proceed through a formal nucleophilic 1,2-addition, thus exhibiting a reactivity complementary to conventional direct arylation through electrophilic substitution.