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Visible-Light-Induced Palladium-Catalyzed Construction of Polyarylfuran Skeletons via Cascade Aryl Radical Cyclization and C(sp<sup>3</sup>)–P(V) Bond Cleavage

Yang Li, Shen‐Yuan Zhang, Xiaolong Yan, Jie Zhu, Kai Luo, Lei Wu

2023Organic Letters16 citationsDOI

Abstract

Herein, a novel and expedient method was established for the synthesis of polyarylfuran derivatives. The coupling of allenylphosphine oxide and bromophenol or bromonaphthol enabled by visible light and palladium catalysis directly furnishes polyarylfuran skeletons, which involves a radical tandem cyclization and cascade C(sp 3 )–P(V) bond cleavage. This protocol features easy operation, a broad substrate scope, and a high step economy, affording polyarylfurans in moderate to good yields.

Topics & Concepts

ChemistryCatalysisPalladiumTandemBond cleavageArylCascadeCleavage (geology)Cascade reactionCombinatorial chemistrySubstrate (aquarium)StereochemistryPhotochemistryOrganic chemistryMaterials scienceFracture (geology)Geotechnical engineeringEngineeringChromatographyOceanographyGeologyAlkylComposite materialCatalytic C–H Functionalization MethodsRadical Photochemical ReactionsSulfur-Based Synthesis Techniques
Visible-Light-Induced Palladium-Catalyzed Construction of Polyarylfuran Skeletons via Cascade Aryl Radical Cyclization and C(sp<sup>3</sup>)–P(V) Bond Cleavage | Litcius