Metal-Catalyzed Methods for Organic Synthesis

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Project Summary/Abstract: The ability to prepare highly functionalized molecules in a general and predictable way is central to organic synthesis and the backbone of drug discovery, development and scale-up. The chemistry that we are proposing involves the development of carbon-heteroatom and carbon- carbon bond formations. Our prior work is widely used throughout academia and industry for the preparation of complex molecules and has become mainstay processes for synthetic chemists. The invention of new methods will not only allow access to important compounds but also the means to be able to efficiently and selectively modify them, to change their properties and or/eliminate side effects. Included in our proposed work are palladium-catalyzed cross coupling methods for the formation of heterocyclic carbon-nitrogen bonds, carbon-oxygen bonds and carbon-fluorine bonds; copper-catalyzed methods for the highly regio-, diastereo-, and enantioselective synthesis of aliphatic amines; and copper-catalyzed methods for the asymmetric formation of carbon-carbon bonds. Mechanistic studies will be conducted to understand the fundamental features of these transformations and will guide us to advance the efficiency and utility of this work. The substrates we are targeting are ubiquitous structural components in pharmaceuticals, natural products, agrochemicals and sensors. The application of these new technologies for the preparation of highly functionalized and diverse compounds, which have previously been inaccessible, will have a great impact in a range of areas that are directly important to human health.