Stereospecific arylation of organolithiums: synthetic, mechanistic and structural investigation

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The discovery of new small molecules for use as drugs, agrochemicals, fragrances etc. relies on the availability of simple precursors that can be incorporated into more complex target molecules. The research we propose will lead to a simple and efficient way of making some classes of molecule currently considered difficult or even impossible to obtain, a limitation which means that some groups of potential targets are currently unavailable. It seeks to develop a transformation in which an aromatic ring becomes bonded to a lithium-bearing carbon atom in such a way that the shape of the starting material is remembered in the product. The products have the common feature of a highly hindered carbon atom carrying an O, N or S substituent - a feature difficult to construct by existing methods. The proposed reactions proceed by a remarkable mechanism, and by joint investigation involving both synthetic organic and structural inorganic chemists we propose to understand why the reaction works the way it does and to use this understanding to develop further related transformations.