A Lutidine‐Bridged Bis‐Perimidinium Salt: Synthesis and Application as a Precursor in Palladium‐Catalyzed Cross‐Coupling Reactions

A novel lutidine‐bridged bis‐perimidinium dibromide 3 was synthesized in quantitative yield from cheap commercial starting materials. The bisylidene prepared therefrom in situ upon deprotonation is a potent precatalyst in palladium‐catalyzed Heck and Suzuki cross‐coupling reactions under aerobic conditions, and is efficient even with a ppm scale catalyst loading. Its stronger σ‐donor character is held to be responsible for its superior catalytic performance compared with imidazole‐ and benzimidazole‐based analogues bearing the same skeleton precursors.