Elucidating the Mechanism and Expanding the Scope of Organometallic Nucleophiles Utilized in the Nickel-Mediated Decarbonylative Cross-Coupling of Substituted Phthalimides

Faculty Mentor(s)

Dr. Jeffrey Johnson

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A new method for synthesizing ortho-substituted benzamides has been developed through the nickel-mediated decarbonylative cross-coupling of substituted phthalimides with diorganozinc reagents. This reaction demonstrates broad substrate scope, including various phthalimides and diorganozinc reagents, with yields up to 96%. However, it requires a stoichiometric equivalent of nickel, which limits its application in synthesis. Efforts to promote catalysis include altering the phthalimide substituent and understanding the mechanism of the reaction using in situ IR and NMR. Recent work has also focused on expanding the scope of nucleophiles to include boronic acids, which are safer and more commercially available than diorganozinc reagents.


This research was funded by the National Science Foundation and Herbert H. and Grace A. Dow Foundation.

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