New Synthetic Applications of Eco-friendly Organometallics of Magnesium, Zinc and Lanthanum in Organic Synthesis

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Polyfunctional organometallics are important building blocks for organic synthesis. In this project, we will develop a new preparation method of polyfunctional Zn-organometallics using a new In(III)-catalyzed zinc insertion to aryl and heteroaryl bromides and iodides. We will study a new preparation of diaryl- and diheteroaryl-magnesium reagents of the type R2Mg-2ROLi in hydrocarbons using a halogen/magnesium-exchange. We will also prepare polyfunctional La-organometallics via a halogen- or sulfoxide-lanthanum-exchange and study their reactivity toward carbonyl groups and other electrophiles. We will prepare new solid zinc Reformatzki-reagents and use these reagents to perform late-stage functionalization of peptides. We will also investigate new Co- and Cr-catalyzed cross-couplings and our main aim is to find reaction conditions allowing a general Csp2-Csp2 cross-coupling between zinc or magnesium organometallics and organic halides. Diastereoselective cross-couplings will also be studied as well as new electrophilic amination reactions. All projects are supported by preliminary experiments and useful synthetic methodologies with academic and industrial applications should result from this research project.