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The Hexameric Resorcinarene Capsule as a Bronsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space.

ABSTRACT: 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 (?-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 Brønsted acid catalyst, for the dehydration of the intermediate alcohol.

SUBMITTER: Gambaro S

PROVIDER: S-EPMC6817573 | biostudies-literature | 2019

REPOSITORIES: biostudies-literature

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The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space.

Gambaro Stefania S La Manna Pellegrino P De Rosa Margherita M Soriente Annunziata A Talotta Carmen C Gaeta Carmine C Neri Placido P

Frontiers in chemistry 20191022

Herein, we show that the hexameric resorcinarene capsule <b>C</b> 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 Brønsted acid catalyst, for the dehydration of the intermediate alcohol. ...[more]

PMID: 31696107

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Carbocation catalysis in confined space: activation of trityl chloride inside the hexameric resorcinarene capsule.

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Kinetic and Thermodynamic Modulation of Dynamic Imine Libraries Driven by the Hexameric Resorcinarene Capsule.

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Base metal-catalyzed benzylic oxidation of (aryl)(heteroaryl)methanes with molecular oxygen.

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Just Add Water: Modulating the Structure-Derived Acidity of Catalytic Hexameric Resorcinarene Capsules.

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Friedel-Crafts Reaction of Acylsilanes: Highly Chemoselective Synthesis of 1-Hydroxy-bis(indolyl)methanes and 1-Silyl-bis(indolyl)methanes Derivatives.

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