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40691-AC1
Novel Lewis Acids in Organic Synthesis

Vladimir Gevorgyan, University of Illinois (Chicago)

During the past year of the grant support, we have spent considerable efforts in investigating the stoichiometric reactions of Lewis acids with various substrates. Previously, we discovered the direct reaction between the triarylborane and terminal alkynes, leading to products of 1,1-carboboration. We have investigated various steric and electronic factors governing the rate and stereochemical outcome of the reaction. Furthermore, we have also found that triarylborane and bulky phosphines react with bismetal species, such as distannane and mixed silylstannanes, resulting in heterolysis of the metal-metal bond. We are currently investigating the scope of metal species that undergo this heterolysis, and the effect different phosphines have on the reaction. Additionally, we have expanded our focus to include other Lewis acids with different substituents in order to find more selective and functional group tolerant catalysts. We have already synthesized various Lewis acids, and have tested them as catalysts in a variety of transformations. We are focusing on finding catalysts that are selective towards only a few reactions, allowing for the development of more functional group compatible reactions.

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