Chiral Biaryl Heterocycles as Ligands for Enantioselective Catalysis

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In this project funded by the Chemical Catalysis program of the NSF Division of Chemistry, Professor Aaron Aponick of the University of Florida is developing a new class of biaryl ligands that will expand the current capabilities of state-of-the-art chemical synthesis through improved catalysis. The fine chemical industry has a multi-billion dollar annual market that heavily relies on catalysis as a means of production. As such, there is a global need for the development of new catalysts and ligands, especially for enantioselective reactions where it is important to be able to modify the structure to finely tune the reaction outcome. This research pursues ligand and catalyst designs with enhanced reactivity and selectivity. The broader impacts of this work stem from gaining an understanding of the fundamental science and application to more advanced systems. The tools developed are widely applicable in a variety of settings and also provide a fertile environment to train students in state-of-the-art techniques for future academic and industrial endeavors. Chemistry Day at a local mall--an informative and educational outreach program--will present science in a public forum known for its wide demographics. The intention is to break down some of the perceived barriers with science among the general public.The proposed research aims to incorporate heterocycles, a class of compounds that are extremely easy to prepare, into a chiral biaryl scaffold. This new class of biaryl ligands capitalizes on an original concept for atropisomerism whereby pi-stacking increases the barrier to rotation and enables the incorporation of electron-rich, 5-membered ring heterocycles in chiral biaryl ligands. The resulting ligands have different steric and electronic properties than known ligands and are readily modified by a highly convergent preparative route. Biaryl ligands may be able to drastically alter the catalytic properties of a system in a predicable and tunable manner.