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Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans <i>via</i> palladium-catalyzed cascade cyclization of alkenyl ethers

Fei Zhou, Can Li, Meng Li, Yangbin Jin, Huanfeng Jiang, Ying‐Jun Zhang, Wanqing Wu

2021Chemical Communications32 citationsDOI

Abstract

A novel palladium-catalyzed cascade cyclization reaction of alkenyl ethers with alkynyl oxime ethers for the construction of poly-heterocyclic scaffolds has been developed, in which the electron-rich alkene moiety functions as a three-atom unit, simultaneously dealing well with the coordination and regioselectivity of electron-rich olefins under metal catalysis. The strategy features excellent regio- and chemoselectivities as well as good functional group tolerance. Moreover, the newly formed 2-isoxazolyl-2,3-dihydrobenzofuran products can be further transformed to diverse complex heterocycles, demonstrating their potential applications in organic synthesis and medicinal chemistry.

Topics & Concepts

CascadePalladiumCatalysisChemistryCascade reactionOximeOrganic chemistryCombinatorial chemistryMedicinal chemistryPolymer chemistryChromatographyCatalytic C–H Functionalization MethodsCatalytic Alkyne ReactionsCyclopropane Reaction Mechanisms
Synthesis of 2-isoxazolyl-2,3-dihydrobenzofurans <i>via</i> palladium-catalyzed cascade cyclization of alkenyl ethers | Litcius