Metal-Catalyzed Methods for Organic Synthesis

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Project Summary: The ability to achieve efficient and selective transformations for the formation of carbon-carbon and carbon-heteroatom bonds is the primary goal of the research described in our parent grant (GM122483). We seek to develop new transition metal-catalyzed methods that are general, user-friendly, and have a significant impact on the field of organic synthesis, particularly in pharmaceutical research. Our current work involves palladium-catalyzed cross coupling for C–N, C–O and C–F bonds and copper-catalyzed processes for the regio- and enantioselective construction of C–N and C–C bonds. In the development of new methods, we try to explore diverse substrate scopes to understand the applicability and generality of these protocols. On average, our published methods each have >20 substrates, we detail the isolated yields of at least two independent experiments to ensure reproducibility and the compounds are purified by flash column chromatography. We are seeking to update and replace our automated chromatography system due to the age of our current equipment (6 and 9 years old) and the number of researchers (33 users) that rely on the system on a daily basis for the purification and isolation of compounds. A new automated system would increase efficiency (2-3 times faster than manual chromatography), decrease solvent waste (environmentally friendly), and have improved reliability (current equipment has had extensive downtime due to repairs). This would greatly facilitate our research efforts in the development and optimization of new methods of C– C and C–X bond formations.