Negishi coupling reactions are commonly used to couple aryl halides with organozinc compounds.  We report the first coupling of N-alkoxybenzimidoyl halides [ArC(X)=NOR] using this technique. For this reaction, the effect of ligands, palladium source, concentrations, additives, temperature, and the type of imidoyl halide have been investigated.  Most of the changes had only a small effect, and the reaction conditions at this time only give moderate yield of the coupling product. Current work shows that an N-alkoxybenzimidoyl bromide works better than the N-alkoxybenzimidoyl iodide in this reaction and leads to less production of the side product of benzonitrile.  Future plans to optimize this reaction will be discussed.

Negishi coupling reaction of <i>N</i>-alkoxybenzimidoyl iodides and bromides

245th National Meeting (2013)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.

Negishi coupling reaction of N-alkoxybenzimidoyl iodides and bromides