Synthesis of γ-Lactams via Nickel Catalyzed Addition of Diorganozinc Nucleophiles to Imides

Student Author(s)

Catherine Calyore

Faculty Mentor(s)

Dr. Jeffery Johnson

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The direct addition of diorganozinc nucleophiles to a range of N-substituted phthalimides has been observed when a catalytic amount of Ni(COD)2 and triphenylphosphine ligand are used in the reaction. Results have shown that aryl substituted Nphthalimides with alkyl and electron deficient groups consistently produce yields around 80%. Diorganozinc reagents used in the reaction include commercially available diethyl zinc, as well as reagents prepared from a wide range of substituted aryl bromides that are utilized without purification. Twelve diarylzinc nucleophiles have been successfully used in the reaction, while seven different N-substituted phthalimides have been used. Current work is being done to further expand the complexity of substituents, as well as incorporating saturated backbones into the reaction. (Original contains diagram)

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