Novel Catalytic Annulation Chemistry

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Vladimir Gevorgyan of the Department of Chemistry at the University of Illinois at Chicago will develop transition metal-catalyzed methodologies towards multi-substituted aromatics and heteroaromatics. Although several methods for construction of benzene rings exist, the known catalytic processes suffer from regioselectivity problems. More selective methods require employment of stoichimetric organometallic reagents, thus severely limiting broad application of these methodologies. These limitations will be addressed in the proposed project through the development of highly efficient Pd-catalyzed [4+2] and formal [2+2+2] benzannulation reactions toward regioselective assembly of a multisubstituted benzene ring. Studies toward new pre- and post-benzannulation cascade transformations will dramatically expand the scope of this methodology. The proposed research, which is at the interface of organometallic and organic chemistry and catalysis, will also provide multidisciplinary training at the undergraduate and graduate level. In addition, Professor Gevorgyan is actively engaged in promoting careers for women in the STEM disciplines. The proposed work is expected to have broader impacts in the health related area by providing new effective routes to biologically important intermediates, and in materials science by allowing easy access to valuable building blocks, which could be utilized in the rapid assembly of complex frameworks and conjugated materials. Moreover, the herein proposed development of "one-pot reactions" may reduce the cost of chemical products and avoid the production of chemical waste, providing both economical and environmental impacts.