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RESEARCH PRODUCT
The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
Carmine GaetaMargherita De RosaPlacido NeriAnnunziata SorientePellegrino La MannaCarmen TalottaStefania Gambarosubject
supramolecular organocatalysisAlcohol02 engineering and technology010402 general chemistry01 natural sciencesCatalysislcsh:Chemistrychemistry.chemical_compoundPolymer chemistryBrønsted acid catalystOriginal ResearchChemistrySubstrate (chemistry)CapsuleH-bond catalystGeneral Chemistryself-assemblyResorcinareneSupramolecular organocatalysis; Resorcinarene hexameric capsule; Bis(heteroaryl)methanes; Self-assembly; H-bond catalyst; Brønsted acid catalyst021001 nanoscience & nanotechnology0104 chemical sciencesChemistrylcsh:QD1-999Self-assembly0210 nano-technologyBrønsted–Lowry acid–base theorySelectivityresorcinarene hexameric capsulebis(heteroaryl)methanesdescription
Herein, we show that the hexameric resorcinarene capsule C is able to catalyze the formation of bis(heteroaryl)methanes by reaction between pyrroles or indoles and carbonyl compounds (α-ketoesters or aldehydes) in excellent yields and selectivity. Our results suggest that the capsule can play a double catalytic role as a H-bond catalyst, for the initial activation of the carbonyl substrate, and as a Bronsted acid catalyst, for the dehydration of the intermediate alcohol.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-10-01 | Frontiers in Chemistry |