New Transition Metal Catalyzed Annulation Chemistry

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The proposed studies are directed toward the development of transition metal catalyzed annulation methodologies for the synthesis of polysubstituted aromatics, heteroaromatics, and monomers for the preparation of conjugated polymers. Sequential cycloaddition/cyclization reactions, triggered by regiocontrolled palladium-catalyzed enyne-yne [4+2] benzannulation, afford condensed aromatic systems. Use of aza-enynes or aza-enynophiles similarly leads to pyridine derivatives. Various related synthetic routes to polysubstituted aromatic systems afford monomers for the synthesis of poly(phenyleneethylene)s and are applicable to the construction of a variety of classes of natural products.With this award, the Organic Synthesis Program supports the studies of Professor Vladimir Gevorgyan, of the Department of Chemistry at the University of Illinois at Chicago. Professor Gevorgyan is discovering and developing new techniques for the synthesis of cyclic and polycyclic organic molecules which represent the core structures of numerous biologically and pharmacologically active compounds. Simple precursors are efficiently converted to the desired target structures through spontaneous cascades of sequential reactions, affording unusual and adaptable new synthetic approaches. These synthetic routes are also applicable to the preparation of precursors for a class of polymers known to display significant electrical and optical properties.