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

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 doub...

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Autores principales: Gambaro, Stefania, La Manna, Pellegrino, De Rosa, Margherita, Soriente, Annunziata, Talotta, Carmen, Gaeta, Carmine, Neri, Placido
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Frontiers Media S.A. 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6817573/
https://www.ncbi.nlm.nih.gov/pubmed/31696107
http://dx.doi.org/10.3389/fchem.2019.00687
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author Gambaro, Stefania
La Manna, Pellegrino
De Rosa, Margherita
Soriente, Annunziata
Talotta, Carmen
Gaeta, Carmine
Neri, Placido
author_facet Gambaro, Stefania
La Manna, Pellegrino
De Rosa, Margherita
Soriente, Annunziata
Talotta, Carmen
Gaeta, Carmine
Neri, Placido
author_sort Gambaro, Stefania
collection PubMed
description 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 Brønsted acid catalyst, for the dehydration of the intermediate alcohol.
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spelling pubmed-68175732019-11-06 The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space Gambaro, Stefania La Manna, Pellegrino De Rosa, Margherita Soriente, Annunziata Talotta, Carmen Gaeta, Carmine Neri, Placido Front Chem Chemistry 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 Brønsted acid catalyst, for the dehydration of the intermediate alcohol. Frontiers Media S.A. 2019-10-22 /pmc/articles/PMC6817573/ /pubmed/31696107 http://dx.doi.org/10.3389/fchem.2019.00687 Text en Copyright © 2019 Gambaro, La Manna, De Rosa, Soriente, Talotta, Gaeta and Neri. http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
spellingShingle Chemistry
Gambaro, Stefania
La Manna, Pellegrino
De Rosa, Margherita
Soriente, Annunziata
Talotta, Carmen
Gaeta, Carmine
Neri, Placido
The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title_full The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title_fullStr The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title_full_unstemmed The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title_short The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space
title_sort hexameric resorcinarene capsule as a brønsted acid catalyst for the synthesis of bis(heteroaryl)methanes in a nanoconfined space
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6817573/
https://www.ncbi.nlm.nih.gov/pubmed/31696107
http://dx.doi.org/10.3389/fchem.2019.00687
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