Nickel-Catalyzed Coupling of Fluoroarenes and Amines

The combination of bis(cyclooctadiene)nickel [Ni(COD)(2)] and 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene hydrochloride (IPrHCl) effectively catalyzes coupling of fluoroarenes with amines in the presence of sodium tert-butoxide (t-BuONa). Activated, unactivated and deactivated fluoroarenes as well as fluoropyridines can react with cyclic or acyclic aliphatic amines. The reactions tolerate various functional groups in the fluorides including PhC(O), C(O)NEt2, CF3, OMe and vinyl groups.