N-Heterocyclic carbene (NHC) containing ligands have been shown to support novel reactivity with first-row transition metal ions. Building on our recent work describing copper(II) catalyzed C—N bond-forming reactions, we report a series of copper(II) N-heterocyclic carbene [CuX2(NHC)] complexes were synthesized from newly prepared pyridine functionalized benzimidazolylide ligand precursors to study the role of pyridine—Cu bonding interactions in the Chan-Lam-Evans reaction. The complexes and pyridine-based benzimidazolylide ligands were characterized and their structures were investigated through 1H and 13C-NMR, HRMS, FTIR, single-crystal X-ray diffraction, UV-Vis, and voltammetry. The reactivity of these complexes was assessed through the well-documented arylation of imidazole and aniline by aryl boronic acid activation.

Synthesis of novel copper(II) NHC complexes of pyridine-functionalized benzimidazolylide ligands and their catalysis in cross-coupling reactions

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