Novel gold(III) complexes are being developed for the functionalization of strong sp3-hybridized C-H bonds. In order to facilitate C-H bond activation, these complexes contain ligands that have the potential to direct C-H bonds toward the gold(III) metal center via chelation. Two types of ligands have been used: 2-tert-butyl-1,10-phenanthroline (tBuPhen) and amide derivatives of 8-aminoquinoline. The reaction of tBuPhen with KAuCl4 in the presence of AgBF4 generates a novel gold(III) complex in which the tBuPhen ligand is bound to gold(III) in a monodentate fashion. When this complex is reacted with excess AgBF4 in acetone-d6, the reaction seems to result in the activation of a strong sp3-hybridized C-H bond in the tert-butyl substituent of the ligand. Under these conditions, AgBF4 appears to be necessary both for the production of the initial tBuPhen-gold complex and for the C-H bond activation; however, attempts at metallation of the 8-aminoquinoline derived ligands in the presence of AgBF4 lead to the production of undesired oxo-bridged gold(III) dimers. In the absence of AgBF4 but in solutions containing both an organic solvent and water, the reaction of these ligands with tetrachloroaurate(III) leads to novel monomeric gold(III) complexes. Further attempts are underway to optimize the syntheses of the gold(III) complexes and to achieve high-yielding C-H bond activation reactions.

Development of gold(III) complexes containing ligands designed for chelation-assisted functionalization of strong, sp3-hybridized C-H bonds

249th National Meeting (2015)

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