Probing the Effects of Various Rhodium Catalysts on the Carbon-Carbon Activation of Quinolinyl Ketones
Dr. Jeffery Johnson
Though the carbon-carbon single bond is thought to be exceptionally stable because of a lack of polarization and steric inaccessibility, it is shown to be functionalizable in the rhodium-catalyzed intramolecular insertion of an alkene into a quinolinyl ketone (Douglas, et. al. J. Am. Chem. Soc. 2009, 131, 412). This reaction was studied kinetically with the use of seven different rhodium(I) catalysts in order to determine the relative rates of the reactions. The procedure was conducted using resealable NMR tubes and the relative amount of product to starting material was tracked with NMR spectroscopy throughout the reactions. Further investigation was done using bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate because of the high rate of reaction discovered in the preliminary experiments. The kinetics of this catalyst were explored by varying the concentration of the starting quinolinyl ketone while holding all other factors constant. The new catalysts researched here could help to increase the rate of these carbon-carbon single bond activating reactions as well as lead to an expansion of the substrate scope.
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