Synthesis of an Unsymmetrical CCC-NHC Pincer Ligand Precursor

Author

Brian Spurlock, University of Mississippi. Sally McDonnell Barksdale Honors CollegeFollow

Date of Award

2014

Document Type

Undergraduate Thesis

Department

Chemistry and Biochemistry

First Advisor

Daniell Mattern

Relational Format

Dissertation/Thesis

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.

Recommended Citation

Spurlock, Brian, "Synthesis of an Unsymmetrical CCC-NHC Pincer Ligand Precursor" (2014). Honors Theses. 141.
https://egrove.olemiss.edu/hon_thesis/141

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