Grainger Group Research

Work in the group is centred around the development of new synthetic methods and strategies, and their application in the synthesis of organic molecules of biological or structural interest. We are also interested in various aspects of organosulfur chemistry, including close-proximity effects associated with peri-substituted dithianaphthalenes and related compounds. We collaborate with University of Birmingham scientists both within the School of Chemistry (Dr Paul Davies on gold-catalysed transformations of organosulfur compounds, Dr Sarah Horswell for electrochemistry measurements) and at the Institute of Clinical Sciences in the Medical School (Dr Sam Butterworth, Professor Nicholas Barnes), where we have recently initiated a medicinal chemistry programme based on the 5-HT3 receptor. Internationally we have collaborated with Professor Steve Bottle (Queensland University of Technology) on nitroxide radicals.

Chemistry we are developing includes the use of reactive intermediates such as carbamoyl radicals and alkylidene carbenes, photochemical cyclisations, [4+3] cycloaddition reactions and diastereotopic group selective desymmetrisation strategies. Further information can be found in our publications. Completed syntheses and current targets within the group are shown below.

The close proximity of atoms at the 1,8-, or peri-, positions of a naphthalene ring often leads to unusual properties, both in terms of structure and reactivity. We are investigating 1,8-dichalcogen (S, Se) derivatives for the generation and stabilization of reactive intermediates in organosulfur chemistry, and as ligands for iron in structural mimics of the active site of [FeFe]-Hydrogenase, the enzyme responsible for the reduction of protons to hydrogen.

Our work has been made possible by the generous financial support of the following: