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Dr. Jeffrey Johnson, Chemistry

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Rhodium-catalyzed decarbonylation reactions have been shown to occur readily with a variety of substituted pyridyl ketones. However, the 2,6-diortho-fluoro pyridyl ketone does not undergo decarbonylation on its own. When testing the unreactive ketone, a reaction was found with boronic acids that leads to an aryl ring exchange and subsequent decarbonylation. This decarbonylation-exchange reaction was further optimized by evaluating three promising sets of experimental conditions. The 2,6-diortho-fluoro ketone was reacted with a series of boronic acids to assess the scope of this transformation using these sets of experimental conditions.


This material is based upon work supported by the National Science Foundation under grant No. 1764118, the Herbert H. and Grace A. Dow Foundation, and the Schaap Endowed Funding for Undergraduate Research.

Title on poster differs from abstract booklet. Poster title: Carbon-Carbon Bond Activation: Optimization of Exchange-Decarbonylation Reactions of Diortho-Fluoro Pyridyl Ketone with Boronic Acids

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