New Horizons in Organic Electron Transfer

Lead Research Organisation: University of Strathclyde
Department Name: Pure and Applied Chemistry


Every school pupil who studies chemistry will be familiar with the reactivity of sodium metal in water. Sodium is an extremely reactive substance and readily loses an electron to become a sodium ion. Other metals also transfer electrons more or less readily.Organic molecules [containing no metals] can transfer an electron if their structures are appropriate. However, it is extremely unusual for a neutral organic molecule to be able to act as a strong electron donor. We have prepared strong electron donors and have discovered the first neutral organic molecule to be able to pass a stern test, i.e. to convert halobenzenes into aryl anions. The reactivity is unprecedented, and it gives us exciting opportunities to make further discoveries.Our aim now is to explore many aspects of the new chemistry to determine how useful it is and to push back the limits of our knowledge. As we move to more and more powerful organic electron donors, we face the tantalising prospect of creating an organic molecule equivalent in reactivity to sodium. However, our molecules would be safer than sodium and could be transported in a form that needs activation in a reaction flask.During this project we will test our molecule to see the limits of its reactivity, and we will design novel families of molecules that behave in an analogous way.


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Description This work led to important advances including publication of the first neutral ground-state organic electron donor (an imidazole-derived donor) that reduced iodoarenes to aryl anions (published in Angew. Chem. Int. Ed)., the reductive cleavage of activated arenesulfonamides and gem-bis-sulfones (J. Am. Chem. Soc.). It also led to a novel DMAP-derived electron donor of equal potency that did all of the above reactions as well as reduction of Weinreb amides and acyloin derivatives. This new donor