A Dinuclear Au(I) Complex with a Pyrene-di-N-heterocyclic Carbene Linker: Supramolecular and Catalytic Studies

Abstract

A digold­(I) complex with a pyrene-di-N-heterocyclic carbene ligand has been obtained and fully characterized. The host–guest properties of the complex were studied in chloroform with a series of polycylic aromatic hydrocarbons (PAHs), and the association constants were determined. The affinity increases with the size of the PAH, with a maximum binding constant of 105 M–1 for the aggregation with coronene. The catalytic activity of the complex was tested in the hydroamination of phenylacetylene with three different amines. The studies showed that the addition of coronene to the reaction medium produces an enhancement of about 20–30% in the activity of the complex.

Dimensional Matching versus Induced‐Fit Distortions: Binding Affinities of Planar and Curved Polyaromatic Hydrocarbons with a Tetragold Metallorectangle

“…The metallorectangle 2 was obtained by following the synthetic procedure shown in Scheme . The deprotonation of di‐ tert ‐butyl‐diethynyl‐carbazole with NaOH in refluxing methanol followed by the addition of the pyrene‐bis‐imidazolydene–gold(I) complex 1 , afforded the tetra‐Au I compound 2 in 71 % yield after purification. When the reaction was carried out in the presence of one equivalent of an electron‐rich PAH (anthracene, pyrene, triphenylene, perylene, coronene or corannulene), the corresponding inclusion complexes (PAH)@ 2 were obtained.…”

Dimensional Matching versus Induced‐Fit Distortions: Binding Affinities of Planar and Curved Polyaromatic Hydrocarbons with a Tetragold Metallorectangle

“…The metallorectangle 2 was obtained by following the synthetic procedure shown in Scheme 1. The deprotonation of di-tert-butyl-diethynyl-carbazole with NaOH in refluxing methanol followed by the addition of the pyrene-bisimidazolydene-gold(I) complex 1, [15] afforded the tetra-Au(I) compound 2 in 71% yield after purification. When the reaction was carried out in the presence of one equivalent of an electron-rich PAH (anthracene, pyrene, triphenylene, perylene, coronene or corannulene), the corresponding inclusion complexes (PAH)@2 were obtained.…”

BIAN‐NHC Ligands in Transition‐Metal‐Catalysis: A Perfect Union of Sterically Encumbered, Electronically Tunable N‐Heterocyclic Carbenes?

“…In 2018, Peris and co‐workers reported the synthesis of a di‐gold(I) complex 34 bearing a π‐extended pyrene NHC ligand (Scheme 39). [75] The catalytic activity of 34 was tested in hydroamination of phenylacetylene with anilines at low catalyst loading. Impressively, up to 900 TON was obtained at 0.05 mol % loading.…”