Two imidazole/pyridinium ligand precursors have been synthesized. Upon reaction with palladium salts these closely related ligands display dissimilar reactivity. The synthesis of the novel NHC-Pd(II) complex, [1,3-bis(N-methylpyridinium-2-ylmethyl)imidazolin-2-ylidene] palladium(II) triiodide is described and supported via 1H and 13C{1H} NMR, elemental analysis, and X-ray crystallography. The catalytic reactivity of [1,3-bis(N-methylpyridinium-2-ylmethyl)imidazolin-2-ylidene] palladium(II) triiodide toward Suzuki and Heck cross-coupling in aqueous and polar organic solvents is also described.

Suzuki and Heck coupling catalyzed by a Pd-NHC/pyridinium complex

255th National Meeting (2018)

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