Nickel-Mediated Decarbonylative Cross-Coupling of Cyclic Imides with Diorganozinc Reagents

Faculty Mentor(s)

Dr. Jeffrey Johnson, Hope College

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This research was supported in part by the Camille and Henry Dreyfus Foundation.


Previous study of a nickel-catalyzed reaction on cyclic anhydrides demonstrated that desymmetrization of these compounds can be achieved with a Ni(COD)2 bipyridal system with diorgano zinc reagents to form β-ketoacids (J. Am. Chem. Soc. 2002, 124, 174-175). This poster outlines the study of a similar reaction on cyclic imides. Instead of forming β-ketoamides as predicted by this previous study, reaction of N-phenyl phthalimide with stoichiometric Ni(COD)2 in the presence of Et2Zn results in a decarbonylation followed by alkylation producing o-ethyl benzanilides. In addition to substitution on the nitrogen of the phthalimide, this reaction has been expanded to the use of diaryl zinc compounds synthesized in situ, along with commercially available diethyl and diphenyl zinc. The recent focus of this project has been to explore the substrate scope in the decarbonylative alkylation/arylation methodology. The scope of these aryl groups has grown to include o-, m-, and p- substituted aryl rings, di- and tri- substituted aryl rings, and substitutions containing electron withdrawing and electron donating groups.

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