SusChEM: New Technologies Based on Organocopper Catalysis

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The Chemical Synthesis Program of the Chemistry Division supports the project by Professor Lipshutz. Professor Lipshutz is a faculty member in the Department of Chemistry at the University of California at Santa Barbara. The project features several new synthetic methods highlighting copper, and to a lesser degree, nickel, as the metals catalyzing the chemistry. The objectives include developing a method to make carbon-carbon bonds using readily available copper as a catalyst rather than palladium, a scarce precious metal. Another objective is the oxidation and cleavage of carbon-carbon double bonds to form carbon-oxygen double bonds using copper catalysis. Each transformation provides a solution to important problems in pharmaceutical development. These processes, in particular those developed to be conducted in water, should encourage process chemists in the fine chemicals and pharmaceuticals areas to consider running their reactions under these sustainable and green chemistry conditions. These projects are well suited for the education of scientists at all levels. Development of undergraduate laboratory experiments using green chemistry principles is a component of this project. Studies conducted under this NSF award focus on the development of new technologies in organocopper chemistry, to be used under green chemistry conditions. These new methods feature use of water as the reaction medium, with the chemistry to be enabled using designer surfactants that provide nanoreactors in which these reactions take place. The methodologies to be studied include (1) a copper-catalyzed Suzuki-Miyaura cross-coupling done with the exclusion of palladium; (2) development of a copper-catalyzed alternative to ozonolysis; and (3) examination of the use of asymmetrically ligated copper(I) for intermolecular hydroaminations of allenes, leading to nonracemic allylic amines. Development of undergraduate laboratory experiments using green chemistry principles is a component of this project.