Gold-Catalyzed Alkyne Multifunctionalization through an Oxidation-Oxyalkylation-Aryloxylation Sequence

A gold-catalyzed oxidative three-component reaction of terminal alkynes with alcohols and quinone monoimines has been disclosed, affording alpha-ketoacetals in good to excellent yields. By using quinone monoimines as electrophiles for the interception of the in situ generated gold enolate intermediate, this one-pot process provides an unprecedented method for the polyfunctionalization of terminal alkynes through an oxidation-oxyalkylation- aryloxylation sequence, installing three oxygen atoms on the C-C triple bond.

Automated summary

A gold-catalyzed oxidative three-component reaction of terminal alkynes with alcohols and quinone monoimines has been developed for the synthesis of alpha-ketoacetals. This one-pot process involves an oxidation-oxyalkylation-aryloxylation sequence, enabling the functionalization of terminal alkynes and introducing three oxygen atoms on the C-C triple bond.