Synthesis of an Unsymmetrical CCC-NHC Pincer Ligand Precursor

Spurlock, Brian (2014) Synthesis of an Unsymmetrical CCC-NHC Pincer Ligand Precursor. Undergraduate thesis, under the direction of Daniell Mattern from Chemistry and Biochemistry, The University of Mississippi.

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Abstract

The purpose of this study was to synthesize a 3-butyl-1-(3-(3-butyl-1H-imidazol-3-ium-1-yl)phenyl)-4,5-dichloro-1H-imidazol-3-ium salt using an Ullmann-type copper coupling reaction. This salt would subsequently be metallated and evaluated for C-H bond activation and luminescence. However, NMR and MS spectra did not show evidence of conversion to the desired product under standard conditions so a model reaction was designed making use of recent findings concerning the Ullmann-type coupling of imidazoles to aryl halides. Specifically, an activated aryl halide with a larger leaving group was used with a more soluble base and a ligand for the copper. The desired product appears by ESI-MS to have been present in the mixture of products at very low yields. This allowed us to make recommendations about future research.

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