813416-08-9Relevant academic research and scientific papers
[1,2]-rearrangement of imino-N-heterocyclic carbenes - Synthesis and structures of chelating iminoimidazole Pd and Ni complexes
Steiner, Georg,Krajete, Alexander,Kopacka, Holger,Ongania, Karl-Hans,Wurst, Klaus,Preishuber-Pfluegl, Peter,Bildstein, Benno
, p. 2827 - 2836 (2007/10/03)
Imidazolium and benzimidazolium salts with an N-iminoyl and an N′-alkyl group are potential precursors for new bidentate [N,C] ligands which are of interest as novel steering ligands for applications of their metal complexes in homogeneous catalysis. Deprotonation of these azolium salts with potassium hydride does indeed occur, however, the initially formed imino-N-heterocyclic carbenes rearrange spontaneously under migration of the N-iminoyl group from the nitrogen to the former carbene carbon with the formation of 2-iminoyl(benz)imidazoles. These rearranged compounds are new [N,N] ligand systems, which can also be synthesized by aluminum-assisted condensation of anilines with the corresponding 2-acylimidazoles. Palladium and nickel [N,N] complexes have been prepared, characterized by single-crystal X-ray analysis, and briefly evaluated for their catalytic performance in ethylene polymerizations and in Suzuki cross-coupling reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
