Acetoxybis(imidazolyl)methylborate [B(ImN-Me)2(OC(O)Me)Me]−: Carboxylation of borane moiety of imidazolyl-based scorpionate

The acetoxy-functionalized bis(imidazolyl)borate [B(ImN-Me)2(OC(O)Me)Me]− (=LOAc) is synthesized by the reaction of the alkoxy precursor [B(ImN-Me)2(OPri)Me]− (=LOiPr) with acetic acid. In the presence of weak Brønstead acid, migration of nickel-bound acetate anion to the boron center giving LOAc occurs. The boron–acetoxy linkage survives upon the treatment of the nickel complexes with OH−, although the acetoxy group on LOAc does not coordinate to the nickel center.

Graphical abstractThe acetoxy-functionalized bis(imidazolyl)borate is formed via replacement of the alkoxide to acetate. In the presence of weak Brønstead acid, migration of nickel-bound acetate anion to the boron center giving the acetoxy-functinalized ligand occurs. The boron–acetoxy linkage survives upon the treatment of the nickel complexes with OH−.Figure optionsDownload full-size imageDownload as PowerPoint slide