Direct cycloauration of 2-anilinopyridine (Hanp) with tetrachloroaurate(III) and the X-ray crystal structure of [AuCl2(anp)]

2-Anilinopyridine (Hanp) reacted with sodium tetrachloroaurate(III) in refluxing water directly to give cyclometallated [AuCl2(anp)], which was characterized spectroscopically and its structure determined by X-ray analysis. The metallation reaction involved direct activation of an ortho C-H bond of the phenyl moiety and the deprotonated anionic ligand, anp, coordinated to Au through-the pyridine-N and phenyl ortho-C atoms forming a six-membered chelate ring. Similarly cycloaurated complexes, [AuBr2(anp)] and [AuCl2(C-N)] (CN = tlp, map, and tpm), were also prepared and characterized (Htlp = 2-(p-toluidino)pyridine, Hmap = 2-(N-methylanilino)pyridine, and Htpm = 2-(p-toluidino)pyrimidine). (C) 1997 Elsevier Science Ltd.