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Palladium-Catalyzed Three-Component Cascade Carbonylation Reaction to Construct Benzofuran Derivatives

Ming Li, Shan-Mei Xu, Dong‐Ping Chen, Fan Gao, Shun‐Xi Li, Shuangxi Zhu, Yi‐Feng Qiu, Zheng‐Jun Quan, Xi‐Cun Wang, Yong‐Min Liang

2024The Journal of Organic Chemistry10 citationsDOI

Abstract

A novel three-component cyclization carbonylation reaction of iodoarene-tethered propargyl ethers with amine and CO is reported. This palladium-catalyzed cascade reaction undergoes a sequence of oxidative addition, unsaturated bond migration, carbonyl insertion, and nucleophilic attack to deliver the benzofuran skeleton. Both aromatic amines and aliphatic amines could proceed smoothly in this transformation under one atm of CO.

Topics & Concepts

ChemistryBenzofuranPalladiumCarbonylationCascade reactionNucleophileCatalysisAmine gas treatingPropargylNucleophilic additionOrganic chemistryCombinatorial chemistryMedicinal chemistryCarbon monoxideCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling ReactionsCatalytic Alkyne Reactions