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Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions

Hongchen Li, Lidong Shan, Lin Min, Yunxiang Weng, Xinyan Wang, Yuefei Hu

2021The Journal of Organic Chemistry12 citationsDOI

Abstract

A TfOH-promoted tandem synthesis of 1,3-disubstituted naphthalenes is developed via a directed-aldol reaction and a Friedel-Crafts reaction. Two new C-C bonds and one new benzene ring are created efficiently in one pot due to the discovery of a TfOH-promoted highly chemoselective directed-aldol reaction between two different ketones with α-hydrogens.

Topics & Concepts

ChemistryAldol reactionFriedel–Crafts reactionTandemBenzeneRing (chemistry)Organic chemistryCascade reactionCombinatorial chemistryCatalysisComposite materialMaterials scienceCatalytic C–H Functionalization MethodsAsymmetric Synthesis and CatalysisSynthesis and Catalytic Reactions
Tandem Synthesis of 1,3-Disubstituted Naphthalenes via TfOH-Promoted Directed-Aldol and Friedel–Crafts Reactions | Litcius