Deactivation of gold(I) catalysts in the presence of thiols and amines--characterisation and catalysis

Abstract

Thiols and amines, which are common heteroatom nucleophiles in gold-catalysed reactions, are known to dampen the reactivity of gold catalysts. In this article, the identity and activity of gold(I) catalysts in the presence of thiols and amines is investigated. In the presence of thioacid, thiophenol and thiol, digold with bridging thiolate complexes [{Au(L)}2(μ-SR)][SbF6] are formed and have been fully characterised by NMR and X-ray crystallography. In the presence of amines and anilines, complexes [LAu-NH2R][SbF6] are formed instead. All new isolated gold complexes were investigated for their catalytic activity in order to compare the level of deactivation in each species.