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...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2019-10-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2019.00687/full |
| _version_ | 1828880694300901376 |
|---|---|
| author | Stefania Gambaro Pellegrino La Manna Margherita De Rosa Annunziata Soriente Carmen Talotta Carmine Gaeta Placido Neri |
| author_facet | Stefania Gambaro Pellegrino La Manna Margherita De Rosa Annunziata Soriente Carmen Talotta Carmine Gaeta Placido Neri |
| author_sort | Stefania Gambaro |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-13T09:53:49Z |
| format | Article |
| id | doaj.art-0ee36b7e379c42058a35303b4e966b80 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-13T09:53:49Z |
| publishDate | 2019-10-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-0ee36b7e379c42058a35303b4e966b802022-12-21T23:51:51ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462019-10-01710.3389/fchem.2019.00687494714The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined SpaceStefania GambaroPellegrino La MannaMargherita De RosaAnnunziata SorienteCarmen TalottaCarmine GaetaPlacido NeriHerein, 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.https://www.frontiersin.org/article/10.3389/fchem.2019.00687/fullsupramolecular organocatalysisresorcinarene hexameric capsulebis(heteroaryl)methanesself-assemblyH-bond catalystBrønsted acid catalyst |
| spellingShingle | Stefania Gambaro Pellegrino La Manna Margherita De Rosa Annunziata Soriente Carmen Talotta Carmine Gaeta Placido Neri The Hexameric Resorcinarene Capsule as a Brønsted Acid Catalyst for the Synthesis of Bis(heteroaryl)methanes in a Nanoconfined Space Frontiers in Chemistry supramolecular organocatalysis resorcinarene hexameric capsule bis(heteroaryl)methanes self-assembly H-bond catalyst Brønsted acid catalyst |
| 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 bronsted acid catalyst for the synthesis of bis heteroaryl methanes in a nanoconfined space |
| topic | supramolecular organocatalysis resorcinarene hexameric capsule bis(heteroaryl)methanes self-assembly H-bond catalyst Brønsted acid catalyst |
| url | https://www.frontiersin.org/article/10.3389/fchem.2019.00687/full |
| work_keys_str_mv | AT stefaniagambaro thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT pellegrinolamanna thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT margheritaderosa thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT annunziatasoriente thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT carmentalotta thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT carminegaeta thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT placidoneri thehexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT stefaniagambaro hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT pellegrinolamanna hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT margheritaderosa hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT annunziatasoriente hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT carmentalotta hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT carminegaeta hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace AT placidoneri hexamericresorcinarenecapsuleasabrønstedacidcatalystforthesynthesisofbisheteroarylmethanesinananoconfinedspace |