Nickel Mediated Decarbonylation of Phthalimides

Jessica L. Kernaghan,* Rebekah C. Krupa, and Jessica M. Hoover
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506

Presentation No.: 106

Assigned Category (Presentation Format): Physical Sciences (Poster Presentations)

Student’s Major: Chemistry

Decarbonylative cross-coupling of aryl compounds has been reported through the application of stoichiometric amounts of nickel complex to form new C-C coupled products, such as the coupling of N-substituted phthalimides with aryl boronic acids. However, nickel catalyzed decarbonylative cross-coupling has only been achieved with diaryl ketones using directing groups to prevent the formation of stable nickel-carbon monoxide complexes. This research focuses on the addition of an 8-aminoquinolinyl to N-substituted phthalimides to determine if catalysis could be achieved through the addition of a directing group. Both stoichiometric and catalytic versions of decarbonylative cross-coupling reactions using N-Phenylphthalimide and N-(8-Quinolinyl)phthalimide were performed for comparison. In both cases, stoichiometric nickel decarbonylative cross-coupling of the N-substituted phthalimides proved to have higher yields than the catalytic versions of the reactions. In particular, the stoichiometric N-(8-Quinolinyl)phthalimide reaction yielded the desired cross-coupled product in addition to the protodemetallated byproduct. Preliminary analysis of the catalytic quinolinyl reaction indicated cross-coupling may have occurred. This would indicate that the addition of a quinolinyl directing group to the N-phthalimide results in catalytic activity.

Funding: CHE-1852369

Program/mechanism supporting research/creative efforts: the WVU Chemistry REU (Brian Popp & Michelle Richards-Babb)