Carbon-carbon Bond Activation: A Kinetic Study of Varying Substrates with Rhodium Catalysis

Carbon-carbon sigma bonds are known to be very stable under most reaction conditions; however, through the use of organometallic chemistry, specifically with rhodium catalysis, we have successfully been able to activate carbon-carbon bonds in quinolinyl ketones and have consequently been able to propose a mechanism for the reaction (JACS, 2009, 131, 412 and JACS, 2011, 133, 2031). Current work has involved expanding the reaction to a variety of substrates by functionalizing one the aromatic rings of the parent quinolynl ketone. Following synthesis of the desired analogs, each is subjected to the carboacylation reaction. Reactions are run in re-sealable NMR tubes and can be performed with as a single reaction with one substrate or a competition reaction with two of the substrates reacting within the same tube. Through analysis of the NMR spectra, we are able to determine the rate of the reaction and ascertain how the functional groups affect the rate. Two different catalysts, Wilkinson’s catalyst and rhodium bis(ethylene) are used during the reaction process and results from these experiments will be presented. Future work will involve continued data collection as well as more extensive rate analysis