Methylation of Amines and Ketones with Methanol Catalyzed by an Iridium Complex Bearing a 2‑Hydroxypyridylmethylene Fragment

Reaction of complex [Cp*Ir­(HOC₅H₃CH₂C₅H₃OH)­Cl]­[Cl] (1) with AgOTf generated the product [Cp*Ir­(HOC₅H₃CH₂C₅H₃OH)­(H₂O)]­[OTf]₂ (2), which was further transformed to the complex [Cp*Ir­(OC₅H₃CH₂C₅H₃O)­(H₂O)] (3) in the presence of t-BuONa via −OH deprotonation. Complexes 1–3 exhibited high activity for the methylation of amines and ketones. These C–C and C–N coupling reactions proceeded in air with 1 mol % catalyst loading in the presence of K₂CO₃.