Rapid Injection NMR Studies of Copper(I) and Copper(III) Organocuprates

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In this project funded by the Chemical Structure, Dynamics and Mechanisms Program of the Chemistry Division, Craig A. Ogle and Michael Murphy of the University of North Carolina at Charlotte will study organocopper reagents using rapid injection (RI) NMR spectroscopy. This approach will further expand the toolkit of synthetic reactions leading to carbon-carbon bond formations. Specifically, the group will improve alkylation reactions using organocuprates so that they are more efficient with fewer side reactions. By developing an understanding of these reactions, the group seeks to make rational changes to the reagents and reaction conditions to allow them to control enantioselectivity. The broader impacts involve training undergraduate and graduate students in the preparation and handling of air-sensitive reagents, the operation of analytical instrumentation, and experimental design. This work will enhance our fundamental understanding about long sought after copper(III) intermediates in organocuprate chemistry. Reactions of organocuprates with other organic functional groups have been a "black box" with much lore associated with their reactivity; This research is focused on separating fact from fiction. The economic impact of this research could be significant, potentially leading to new products and methodologies in the pharmaceutical industry.