A Mechanistic Inquiry into Rhodium-Catalyzed C-C Single Bond Activation in Quinolinyl Ketones

Faculty Mentor(s)

Dr. Jeffrey Johnson, Hope College

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This work is supported by the Research Corporation.


Carbon-carbon single bonds are highly stable and inert under most reaction conditions, but can be made to break and form using a rhodium catalyst. The purpose of this research project is to determine the mechanism for the rhodium-catalyzed activation of C-C single bonds in quinolinyl ketones with appended alkenes (JACS, 2009, 131, 412). Competition reactions were run between differentially substituted quinolinyl ketones to see how the substrate affected the reaction rate. Using {RhCl(C2H4)2}2, it was observed that differing the alkene substrate changed the reaction rate greatly, while substitution around the benzene ring had a much smaller effect. From these results, we were able to narrow down where the rate-limiting step of the proposed mechanism occurred. These results are in contrast, however, to the results obtained using RhCl(PPh3)3, suggesting different mechanistic behaviors for these two rhodium catalysts.

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