Rhodium-Catalyzed Carboacylation with Quinolinyl Ketones: Evidence for Rate-Limiting C-C Bond Activation
Dr. Jeffrey Johnson, Hope College
Carbon-carbon single bond activation reactions promise to revolutionize organic synthesis by opening the doors to new, more efficient synthetic methods. The rhodium-catalyzed intramolecular carboacylation of quinolinyl ketones serves as an ideal subject for the mechanistic study of carbon-carbon bond activation. Combined kinetic and NMR studies of this reaction allowed the identification of the catalytic resting state and determination of the rate law, 12C/13C kinetic isotope effects, and activation parameters. These results have identified the activation of a ketone-arene carbon-carbon single bond as the turnover limiting step of catalysis and provided quantitative detail into this process.
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