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(Im(N-Me))(2)(OC(=O)Me)Me] (=L-OAc) is synthesized by the reaction of the alkoxy precursor [B(Im(N-Me))(2)(OPri)Me] (=L-OiPr) with acetic acid. In the presence of weak Bronstead acid, migration of nickel-bound acetate anion to the boron center giving L-OAc occurs. The boron-acetoxy linkage survives upon the treatment of the nickel complexes with OH, although the acetoxy group on L-OAc does not coordinate to the nickel center. (C) 2009 Elsevier B. V. All rights reserved.