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Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation

In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different condit...

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Autores principales: Uzunlu, Nuray, Pongrácz, Péter, Kollár, László, Takács, Attila
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9823927/
https://www.ncbi.nlm.nih.gov/pubmed/36615634
http://dx.doi.org/10.3390/molecules28010442
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author Uzunlu, Nuray
Pongrácz, Péter
Kollár, László
Takács, Attila
author_facet Uzunlu, Nuray
Pongrácz, Péter
Kollár, László
Takács, Attila
author_sort Uzunlu, Nuray
collection PubMed
description In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh(3). Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles.
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spelling pubmed-98239272023-01-08 Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation Uzunlu, Nuray Pongrácz, Péter Kollár, László Takács, Attila Molecules Article In this research, ethyl levulinate, methyl levulinate, and 2-methyltetrahydrofuran as bio-derived hemicellulose-based solvents were applied as green alternatives in palladium-catalyzed aminocarbonylation reactions. Iodobenzene and morpholine were used in optimization reactions under different conditions, such as temperatures, pressures, and ligands. It was shown that the XantPhos ligand had a great influence on conversion (98%) and chemoselectivity (100% carboxamide), compared with the monodentate PPh(3). Following this study, the optimized conditions were used to extend the scope of substrates with nineteen candidates (various para-, ortho-, and meta-substituted iodobenzene derivatives and iodo-heteroarenes), as well as eight different amine nucleophiles. MDPI 2023-01-03 /pmc/articles/PMC9823927/ /pubmed/36615634 http://dx.doi.org/10.3390/molecules28010442 Text en © 2023 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Uzunlu, Nuray
Pongrácz, Péter
Kollár, László
Takács, Attila
Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title_full Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title_fullStr Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title_full_unstemmed Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title_short Alkyl Levulinates and 2-Methyltetrahydrofuran: Possible Biomass-Based Solvents in Palladium-Catalyzed Aminocarbonylation
title_sort alkyl levulinates and 2-methyltetrahydrofuran: possible biomass-based solvents in palladium-catalyzed aminocarbonylation
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9823927/
https://www.ncbi.nlm.nih.gov/pubmed/36615634
http://dx.doi.org/10.3390/molecules28010442
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