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Palladium‐Catalyzed Three‐Component Reactions for the Synthesis of Norbornane‐Fused Indanes

Xiaoming Ji, Yichao Gu, Cang Cheng, Zhuo Wu, Yanghui Zhang

2020Advanced Synthesis & Catalysis20 citationsDOI

Abstract

Abstract Two methods for the synthesis of norbornane‐fused indanes via palladium‐catalyzed three‐component reactions of iodoarenes, norbornenes, and CH 2 Br 2 or α ‐diazoesters have been developed. In the reactions, three C−C bonds were constructed and a wide range of norbornane‐fused indanes could be synthesized. The reactions with α ‐diazoesters proceeded with a high degree of diastereoselectivity and indanes bearing an all‐carbon quaternary center were formed. The products obtained in the reactions of 1,4‐dihydro‐1,4‐epoxynaphthalene can be converted to fluorenes, providing an alternative way to access fluorene derivatives. magnified image

Topics & Concepts

NorbornaneChemistryPalladiumCatalysisFluoreneOrganic chemistryPolymerCatalytic C–H Functionalization MethodsCyclopropane Reaction MechanismsCatalytic Cross-Coupling Reactions
Palladium‐Catalyzed Three‐Component Reactions for the Synthesis of Norbornane‐Fused Indanes | Litcius