Carbon-Carbon Single Bond Activation Used for Coupling with Michael Acceptors

Faculty Mentor(s)

Dr. Jeffrey Johnson

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Intramolecular alkene carboacylation has previously been achieved under rhodium catalysis using quinolinyl ketones. Utilizing insight gained from mechanistic studies, new quinolinyl ketone substrates have been prepared and subjected to rhodium catalysis in the presence of an exogenous alkene. This project provides an overview of the development of a new transition metal catalyzed reaction that yields an unexpected product—rather than the anticipated reaction sequence, substrates undergo carbon-carbon bond activation, and Heck-type reactivity is observed via oxidative nucleophilic addition to various Michael acceptors. The reaction proceeds in good to excellent yield with a broad range of functionality on both substrates.


This research was supported by the John R. Soeter Student/Faculty Research Fund, the National Science Foundation, and the Schaap Research Fellowship from Hope College.

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