Investigation of Regioselectivity in the Nickel-Mediated Decarbonylative Cross-Coupling of Imides with Organozinc Reagents

Faculty Mentor(s)

Dr. Jeffrey Johnson, Hope College

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Recent studies have demonstrated a nickel/bipy-mediated decarbonylative cross-coupling of cyclic imides with diorganozinc reagents. This reaction has been demonstrated with a wide range of N-substituted phthalimides and with a variety of organozinc nucleophiles. In order to gain additional mechanistic insight into this transformation, a series of 3- and 4-substituted imides were prepared and subjected to decarbonylative alkylation. The reactions were analyzed through GC and NMR spectroscopy to determine the regioselectivity of the resulting products. This presentation will detail these efforts and outline efforts to control regioselectivity within this reaction manifold.


This material is based upon work supported by the Henry and Camille Dreyfus Foundation.

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