Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst
Microwaves (MW) are often the most efficient, in terms of heat exchange and conversion rate, of all the energy sources used to promote chemical reactions thanks to fast volumetric dielectric heating, and metal-catalyzed synthetic reactions under heterogeneous conditions are an eloquent example. We h...
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Frontiers Media S.A.
2020-04-01
|
| Series: | Frontiers in Chemistry |
| Subjects: | |
| Online Access: | https://www.frontiersin.org/article/10.3389/fchem.2020.00253/full |
| _version_ | 1828853339811479552 |
|---|---|
| author | Silvia Tabasso Emanuela Calcio Gaudino Elisa Acciardo Maela Manzoli Barbara Bonelli Giancarlo Cravotto |
| author_facet | Silvia Tabasso Emanuela Calcio Gaudino Elisa Acciardo Maela Manzoli Barbara Bonelli Giancarlo Cravotto |
| author_sort | Silvia Tabasso |
| collection | DOAJ |
| description | Microwaves (MW) are often the most efficient, in terms of heat exchange and conversion rate, of all the energy sources used to promote chemical reactions thanks to fast volumetric dielectric heating, and metal-catalyzed synthetic reactions under heterogeneous conditions are an eloquent example. We herein report a MW-assisted green protocol for the C-H arylation of thiophenes with substituted aryl halides. This sustainable protocol carried out in γ-valerolactone (GVL) is catalyzed by Pd nanoparticles embedded in cross-linked β-cyclodextrin. In view of the excellent results achieved with activated substrates, the one-pot synthesis of a 4(3H)-quinazolinone derivative has been accomplished. A pressure-resistant MW reactor, equipped with multiple gas inlets, was used for sequential (i) C-H arylation, (ii) reduction, and (iii) carbonylation in the presence of the same catalyst, but under different gas atmospheres. The robust heterogeneous Pd catalyst showed limited metal leaching in GVL, making this an efficient MW-assisted process with high atom economy. |
| first_indexed | 2024-12-13T00:11:45Z |
| format | Article |
| id | doaj.art-d402e2f46ebc47dc9e5a473986e6439a |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-13T00:11:45Z |
| publishDate | 2020-04-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-d402e2f46ebc47dc9e5a473986e6439a2022-12-22T00:05:56ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462020-04-01810.3389/fchem.2020.00253522292Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked NanocatalystSilvia Tabasso0Emanuela Calcio Gaudino1Elisa Acciardo2Maela Manzoli3Barbara Bonelli4Giancarlo Cravotto5Dipartimento di Chimica, University of Turin, Turin, ItalyDipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Turin, ItalyDipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Turin, ItalyDipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Turin, ItalyDepartment of Applied Science and Technology, Politecnico di Torino, Turin, ItalyDipartimento di Scienza e Tecnologia del Farmaco and NIS, Centre for Nanostructured Interfaces and Surfaces, University of Turin, Turin, ItalyMicrowaves (MW) are often the most efficient, in terms of heat exchange and conversion rate, of all the energy sources used to promote chemical reactions thanks to fast volumetric dielectric heating, and metal-catalyzed synthetic reactions under heterogeneous conditions are an eloquent example. We herein report a MW-assisted green protocol for the C-H arylation of thiophenes with substituted aryl halides. This sustainable protocol carried out in γ-valerolactone (GVL) is catalyzed by Pd nanoparticles embedded in cross-linked β-cyclodextrin. In view of the excellent results achieved with activated substrates, the one-pot synthesis of a 4(3H)-quinazolinone derivative has been accomplished. A pressure-resistant MW reactor, equipped with multiple gas inlets, was used for sequential (i) C-H arylation, (ii) reduction, and (iii) carbonylation in the presence of the same catalyst, but under different gas atmospheres. The robust heterogeneous Pd catalyst showed limited metal leaching in GVL, making this an efficient MW-assisted process with high atom economy.https://www.frontiersin.org/article/10.3389/fchem.2020.00253/fullmicrowavesheterogeneous catalysisbio-based solventC-H arylationfluorescent quinazolinoneone-pot synthesis |
| spellingShingle | Silvia Tabasso Emanuela Calcio Gaudino Elisa Acciardo Maela Manzoli Barbara Bonelli Giancarlo Cravotto Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst Frontiers in Chemistry microwaves heterogeneous catalysis bio-based solvent C-H arylation fluorescent quinazolinone one-pot synthesis |
| title | Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst |
| title_full | Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst |
| title_fullStr | Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst |
| title_full_unstemmed | Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst |
| title_short | Microwave-Assisted Protocol for Green Functionalization of Thiophenes With a Pd/β-Cyclodextrin Cross-Linked Nanocatalyst |
| title_sort | microwave assisted protocol for green functionalization of thiophenes with a pd β cyclodextrin cross linked nanocatalyst |
| topic | microwaves heterogeneous catalysis bio-based solvent C-H arylation fluorescent quinazolinone one-pot synthesis |
| url | https://www.frontiersin.org/article/10.3389/fchem.2020.00253/full |
| work_keys_str_mv | AT silviatabasso microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst AT emanuelacalciogaudino microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst AT elisaacciardo microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst AT maelamanzoli microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst AT barbarabonelli microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst AT giancarlocravotto microwaveassistedprotocolforgreenfunctionalizationofthiopheneswithapdbcyclodextrincrosslinkednanocatalyst |