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Cationic-lanthanide-complex-catalyzed reaction of 2-hydroxychalcones with naphthols: Facile synthesis of 2,8-dioxabicyclo[3.3.1]nonanes

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Abstract Cationic lanthanide complexes [Ln(CH3CN)9]3+[(AlCl4)3]3–·CH3CN served as efficient catalysts for the tandem Friedel–Crafts alkylation/ketalization reaction of 2-hydroxychalcones with naphthols/substituted phenols to produce diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes in moderate to high yields. The… Click to show full abstract

Abstract Cationic lanthanide complexes [Ln(CH3CN)9]3+[(AlCl4)3]3–·CH3CN served as efficient catalysts for the tandem Friedel–Crafts alkylation/ketalization reaction of 2-hydroxychalcones with naphthols/substituted phenols to produce diaryl-fused 2,8-dioxabicyclo[3.3.1]nonanes in moderate to high yields. The high catalytic efficiency of the cationic lanthanide complex [Yb(CH3CN)9]3+[(AlCl4)3]3–·CH3CN compared with that of YbCl3 can be attributed to the increased Lewis acidity of the Yb species as a result of cation formation.

Keywords: reaction hydroxychalcones; dioxabicyclo nonanes; lanthanide; hydroxychalcones naphthols; cationic lanthanide; lanthanide complex

Journal Title: Tetrahedron
Year Published: 2018

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