Novel gold(III) complexes are being developed for the functionalization of strong sp3-hybridized C-H bonds. The complexes contain ligands that have the potential to direct these types of 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 (AdQuin). No reactions were observed when ligand and AuCl4- were combined in organic solvents at room temperature. Ligations of gold(III) were observed when either AgBF4 or water were added to the reaction mixture. Under both sets of conditions, tBuPhen bound in a monodentate fashion to gold(III), generating (tBuPhen)AuCl3. The AdQuin ligands did not undergo metallation reactions with AuCl4- when the reactions were performed in organic solvents with AgBF4. However, they did bind to gold(III) when the reactions were performed in the absence of AgBF4 and instead in organic/aqueous solvent mixtures. The AdQuin ligands seem to most commonly bind to gold(III) in a bidentate manner, but the steric bulk of the amide seems to impact binding modes, geometries, and absorbance spectra.

Synthesis of gold(III) complexes containing phenanthroline- or quinoline-based ligands

253rd National Meeting (2017)

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