A Lutidine‐Bridged Bis‐Perimidinium Salt: Synthesis and Application as a Precursor in Palladium‐Catalyzed Cross‐Coupling Reactions
2009
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.
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