Nickel-Catalyzed Cross-Electrophile Coupling of 2-Chloropyridines with Alkyl Bromides

The synthesis of 2-alkylated pyridines by the nickel-catalyzed cross-coupling of two electrophiles, a 2-chloropyridine and an alkyl bromide, is described. Compared with our previously published conditions for aryl halides, this method uses a different, more rigid, bathophenanthroline ligand and is conducted at high concentration in N,N-dimethylformamide as solvent. The method displays promising functional group compatibility and the conditions are ­orthogonal to those for the Stille coupling.