Discovery and Optimization of Nickel-Mediated and Rhodium-Catalyzed Cross-Coupling Reactions

Student Author(s)

Joseph Dennis

Faculty Mentor(s)

Dr. Jeffrey Johnson

Document Type


Event Date



Continued exploration of a nickel-catalyzed decarbonylative cross-coupling of N-substituted phthalimides and in-situ prepared diorganozinc nucleophiles has prompted the study of intramolecular, decarbonylative cross-coupling reactions. The previously studied diorganozinc coupling reaction proceeds through an intermediate capable of intercepting both nucleophiles and p systems. With this insight, a variety of pendant substituents were screened in pursuit of synthesizing a range of cyclic amide compounds. In a second system, a variety of alkyl and aryl boronic acids were coupled to quinolinyl ketones through an intermediate generated through rhodium-catalyzed carbon-carbon bond activation. Current work is being done to optimize reaction conditions and to incorporate a variety of boron reagents, including boronic acids, esters, and borates.


This research was supported by ACS PRF, the Towsley Foundation, and the Hope College Chemistry Department.

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