Gold-Catalyzed Alkyne Multifunctionalization through an Oxidation–Oxyalkylation–Aryloxylation Sequence
Weichen Xiong, Su Zhou, Xinke Zhang, Jingyu Zhao, Jingjing Huang, Wenhao Hu, Xinfang Xu
Abstract
A gold-catalyzed oxidative three-component reaction of terminal alkynes with alcohols and quinone monoimines has been disclosed, affording α-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.
Topics & Concepts
ChemistryAlkyneElectrophileCatalysisQuinoneSequence (biology)Triple bondCombinatorial chemistryTerminal (telecommunication)Medicinal chemistryStereochemistryOrganic chemistryDouble bondBiochemistryTelecommunicationsComputer scienceCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsOxidative Organic Chemistry Reactions