Synthesis and applications of organobismuth reagents
Publication Date
July 29, 2026
Creator
Fox, Andrew
University of Nottingham
Abstract
Bismuth and its compounds have found uses as materials and reagents due to their physical and chemical properties, as well as their low toxicity. The Ball group have previously developed electrophilic arylation methodologies utilising an organobismuth compound based on the diphenyl sulfone scaffold. This thesis focuses on improving the usefulness of these organobismuth-based arylating agents by improving the reagent synthesis and their applications. To this end, four strategies were investigated.
A one-step procedure using commercially available reagents was designed to streamline the synthesis to obtain a high purity and easily filterable bismacycle product. A solvent screen guided by the design of experiments (DoE) approach was performed to maximise the isolated yield of product from recrystallisation.
The second project builds on the utility of the bismacycle by expanding the scope to non-sp2 electrophiles. This led to the investigation of the feasibility of Bi(V)-mediated ligand coupling to install a cyclopropyl group onto nucleophiles.
The third project focuses on catalytic C-C bond formation using organobismuth compounds. Novel organobismuth compounds were designed to enable oxidation using milder oxidants. Two novel compounds were synthesised and tested, which showed C-arylation activity, demonstrating the potential of these novel backbones. The diphenyl sulfone scaffold was revisited to attempt untested combinations of oxidants, substrates and conditions.
The fourth and final project expands on the stoichiometric arylation of nitroalkanes. Arylations of nitroalkanes using ortho-substituted aryl groups was pursued, in conjunction with the synthesis of γ-amino butyric acids (GABA) precursors, of which the final products have pharmaceutical applications.
Item Type
ethesis
Thesis Type
PhD
Supervisors
Ball, Liam
University of Nottingham
Denton, Ross
University of Nottingham
Subjects (LC)
Associated Schools / Departments
Related Publication URL(s)
UoN Repository URI
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