Development of a Nickel-Catalyzed Decarbonylative Cross-Coupling Reaction of Cyclic Imides

A decarbonylative cross-coupling of N-substituted cyclic imides occurs in a reaction with diorganozinc reagents in the presence of stoichiometric Ni(COD)2 or Ni(acac)2 and a bipyridine ligand, producing o-substituted benzanilides (J. Org. Chem., 2011, 76, 3588). Diorganozinc reagents used include diethyl zinc and a wide variety of in situ synthesized diarylzinc compounds including o-, m-, and p- substituted aryl rings, di- and tri- substituted aryl rings, and substitutions containing electron withdrawing and electron donating groups. Conditions for the development of the more desirable catalytic reaction have been explored by varying the solvent and ligands in order to favor the disassociation of CO from nickel and result in catalytic turnover. The highest turnover observed with the decarbonylative product occurred with 4,4’-dimethoxy-2,2’-bipyridine in DMF. Further studies will be done to develop the catalytic function of this decarbonylative reaction