Synthesis, structural characterization of benzimidazole-functionalized Ni(II) and Hg(II) N-heterocyclic carbene complexes and their applications as efficient catalysts for Friedel-Crafts alkylations |
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| Authors: | Guoli Huang Xiaojie Qiu Juli Jiang Leyong Wang |
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| Institution: | a Key Laboratory of Mesoscopic Chemistry, Ministry of Education and School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, China
b College of Material Science and Technology, Nanjing University of Aeronautics and Astronautics, Nanjing 210000, China |
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| Abstract: | Ni(L1)2](PF6)2 (3a, L1 = 3-(1-ethyl-1H-benzimidazol-2-yl)methyl)-1-((6-methylpyridin-2-yl)methyl)imidazolyl-idene), Ni(L2)2(CH3CN)](PF6)2 (3b, L2 = 3-(1-ethyl-1H-benzimidazol-2-yl)methyl)-1-((6-methylpyridin-2-yl)-methyl)benzimidazolylidene), and Hg(L1)2(CH3CN)2](PF6)2 (4) have been successfully prepared and fully characterized by NMR, ESI-MS spectroscopy, and X-ray diffraction analysis. The nickel complexes reveal a square-planar structure with two carbene ligands and benzimidazole groups at the cis configuration. The nickel complex 3b has been proved to be a highly efficient catalyst for Friedel-Crafts alkylation of indoles with β-nitrostyrenes at room temperature in moderate-to-excellent yields. The crystal packing structure of 4 shows that double-stranded 1D supramolecular chains are formed by inter-chain benzimidazole rings and pyridine rings face-to-face π-π stacking interactions. |
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| Keywords: | N-Heterocyclic carbene Nickel Mercury Friedel-Crafts alkylation Indole Catalysis |
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