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.