Carbophilic activation of π-systems via gold coordination: Towards regioselective access of intermolecular addition products

Abstract The utilization of intermolecular addition of carbon–carbon π-bonded systems as atom-economical approach is a topic of significant interest in synthetic organic chemistry. Apart from traditional strategies, gold salts and gold complexes in the last two decades have emerged as frontline catalysts for nucleophilic and electrophilic addition of π-systems via carbophilic activation. Towards this end, the dexterity of gold in catalyzing the intermolecular addition of carbon–carbon π-bonded systems with diverse functionalities was disclosed in this review. In particular, the current review focuses on the realization of catalytic application of gold in affecting addition of different classes of substrates with particular emphasis on regioselectivity. Depending on the type of heteroatoms or functional group (halides, alcohols, carboxylic acids, phosphoric acids, sulphonic acids, amines, amides, hydrazines, azides, carbon, sulphur, silyls and metals) that undergoes addition towards the given π-system (alkenes, dienes, alkynes, allenes, allenamides, ynamides), this review is organized in several sections. Discussions pertaining to reaction mechanism for the gold-catalyzed regioselective additions are also included when appropriate.