C-C Bond Activation: Functionalizing Quinolinyl Ketones for Rhodium Catalysis

Student Author(s)

Michael Pietrangelo

Faculty Mentor(s)

Dr. Jeffery Johnson

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Being able to utilize carbon-carbon single bonds can allow for numerous new pathways in organic synthesis. These pathways can be more efficient, faster, and more reliable than their counterparts. Rhodium catalysis is the process utilized to conduct C-C bond activation in quinolinyl ketones(Douglas, et. al. J. Am. Chem. Soc. 2009, 131, 412). In the literature quinolinyl ketones have been limited to only one substrate during rhodium catalysis: A new parent compound was synthesized with a phenol in place of the alkene tail in order to conduct Williamson ether syntheses to form different Quinolinyl substrates. Different alkyne and ketone substituted groups have been successfully added. Those new substrates were found to react in the presence of Wilkinson’s catalyst using the exact same conditions as the parent reaction (above). (Original contains diagram)

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