Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles
Palladium-catalyzed carbonylation reactions of <i>ortho</i>-phenylene dihalides were studied using aminoethanols as heterobifunctional <i>N</i>,<i>O</i>-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine an...
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MDPI AG
2024-11-01
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| author | Fanni Bede Attila Takács László Kollár Péter Pongrácz |
| author_facet | Fanni Bede Attila Takács László Kollár Péter Pongrácz |
| author_sort | Fanni Bede |
| collection | DOAJ |
| description | Palladium-catalyzed carbonylation reactions of <i>ortho</i>-phenylene dihalides were studied using aminoethanols as heterobifunctional <i>N</i>,<i>O</i>-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production. Intramolecular double carbonylation reaction can be achieved using 1,2-diiodobenzene and amino alcohols featuring secondary amine groups, giving oxazocine derivatives. Useful reaction scope with various amino alcohols was performed with good isolated yields of the targeted compounds. Intramolecular C-O coupling of amide alcohols possessing bromo substituent in adjacent <i>ortho</i> position is also demonstrated as a potential next step in benzoxazepine heterocycle formation. |
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| issn | 1420-3049 |
| language | English |
| publishDate | 2024-11-01 |
| publisher | MDPI AG |
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| series | Molecules |
| spelling | doaj-art-74f45b95e979476ea080cab67a619f322025-08-20T02:38:50ZengMDPI AGMolecules1420-30492024-11-012923562010.3390/molecules29235620Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-NucleophilesFanni Bede0Attila Takács1László Kollár2Péter Pongrácz3Department of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, HungaryHUN-REN-PTE Research Group for Selective Chemical Syntheses, Ifjúság u. 6., H-7624 Pécs, HungaryDepartment of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, HungaryDepartment of General and Inorganic Chemistry, University of Pécs, Ifjúság u. 6., H-7624 Pécs, HungaryPalladium-catalyzed carbonylation reactions of <i>ortho</i>-phenylene dihalides were studied using aminoethanols as heterobifunctional <i>N</i>,<i>O</i>-nucleophiles. The activity of aryl-iodide and -bromide as well as the chemoselective transformation of amine and hydroxyl functionalities were studied systematically under carbonylation conditions. Aminocarbonylation can be selectively realized under optimized conditions, enabling the formation of amide alcohols, and the challenging alkoxycarbonylation can also be proved feasible, enabling amide-ester production. Intramolecular double carbonylation reaction can be achieved using 1,2-diiodobenzene and amino alcohols featuring secondary amine groups, giving oxazocine derivatives. Useful reaction scope with various amino alcohols was performed with good isolated yields of the targeted compounds. Intramolecular C-O coupling of amide alcohols possessing bromo substituent in adjacent <i>ortho</i> position is also demonstrated as a potential next step in benzoxazepine heterocycle formation.https://www.mdpi.com/1420-3049/29/23/5620carbonylationpalladiumhomogeneous catalysisamino alcoholcarbon monoxidebifunctional nucleophile |
| spellingShingle | Fanni Bede Attila Takács László Kollár Péter Pongrácz Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles Molecules carbonylation palladium homogeneous catalysis amino alcohol carbon monoxide bifunctional nucleophile |
| title | Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles |
| title_full | Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles |
| title_fullStr | Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles |
| title_full_unstemmed | Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles |
| title_short | Palladium-Catalyzed Selective Carbonylation Reactions of <i>Ortho</i>-Phenylene Dihalides with Bifunctional <i>N</i>,<i>O</i>-Nucleophiles |
| title_sort | palladium catalyzed selective carbonylation reactions of i ortho i phenylene dihalides with bifunctional i n i i o i nucleophiles |
| topic | carbonylation palladium homogeneous catalysis amino alcohol carbon monoxide bifunctional nucleophile |
| url | https://www.mdpi.com/1420-3049/29/23/5620 |
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