Decarboxylation of aromatic carboxylic acids by gold(i)-N-heterocyclic carbene (NHC) complexes

Abstract

A recently isolated gold(I) complex, [Au(IPr)(OH)], permits the transformation of carboxylic acids to the corresponding decarboxylated gold(I)-aryl complex without the use of silver co-catalyst under mild reaction conditions.

Gold(I)‐Catalyzed Protodecarboxylation of (Hetero)Aromatic Carboxylic Acids

“…In 2010, we reported a straightforward procedure to obtain stable aryl gold complexes by decarboxylation of (hetero)aromatic carboxylic acids with the Brønsted base [Au(IPr)(OH)] (IPr=1,3‐bis(2,6‐diisopropylphenyl)‐imidazol‐2‐ylidene) complex at low temperature 10. This first insight into the decarboxylation reaction with gold revealed a similar reactivity trend to silver.…”

Transition metal-catalyzed decarboxylative cross-coupling reactions

“…However, because Au complexes have been regarded inert for the past several decades and also because of the high price of Au catalysts, few studies have been carried out to examine Au-catalyzed protodecarboxylation. Very recently Nolan et al reported the first example of the Au(I)-mediated decarboxylation of aromatic acids [12]. Surprisingly, the products are not protonated because the reaction stops at the metallation (i.e.…”

Umwandlung von Kohlendioxid mit Übergangsmetall‐Homogenkatalysatoren: eine molekulare Lösung für ein globales Problem?

“…Dies ist üblicherweise -wie in allen bisherigen Fällen beschrieben -aufwändig, und häufig ist es nçtig, den Metallkomplex zu hydrolysieren, was eine Katalyse unmçg-lich macht. [132] Nolan et al zeigten ebenfalls, dass analoge Kupferkatalysatoren ähnliche Aktivitäten aufweisen und erweiterten ihre Studien auf andere Substrate mit sauren Element-Wasserstoff-Bindungen, wie Imidazole, was zu einer N-Carboxylierung N-heterocyclischer Verbindungen führte. [133] Zahlrei- den.…”