Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid
This article presents an experimental kinetic study of the Suzuki–Miyaura reaction of 4-iodoacetophenone with phenylboronic acid catalyzed by the Herrmann–Beller palladacycle. This catalyst, together with the solvent (ethanol) and the base (sodium methylate), were chosen to ensure catalyst stability...
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MDPI AG
2020-09-01
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| Series: | Catalysts |
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| Online Access: | https://www.mdpi.com/2073-4344/10/9/989 |
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| author | Amine Bourouina Alexis Oswald Valentin Lido Lu Dong Franck Rataboul Laurent Djakovitch Claude de Bellefon Valérie Meille |
| author_facet | Amine Bourouina Alexis Oswald Valentin Lido Lu Dong Franck Rataboul Laurent Djakovitch Claude de Bellefon Valérie Meille |
| author_sort | Amine Bourouina |
| collection | DOAJ |
| description | This article presents an experimental kinetic study of the Suzuki–Miyaura reaction of 4-iodoacetophenone with phenylboronic acid catalyzed by the Herrmann–Beller palladacycle. This catalyst, together with the solvent (ethanol) and the base (sodium methylate), were chosen to ensure catalyst stability and reactants solubility all along the reaction. Based on the study of initial reaction rates, a quasi-first-order was found for 4-iodoacetophenone with a first-order dependence on the initial concentration of palladium. A zero-order was found for the base and the phenylboronic acid. The oxidative addition step of the mechanism was thus considered as the rate determining step. A global rate law was derived and validated quantitatively. A global activation energy, with an average value of ca. 63 kJ/mol was determined. |
| first_indexed | 2024-03-10T16:40:18Z |
| format | Article |
| id | doaj.art-fb8162e9d0df4d94990e0f83ed02aa31 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T16:40:18Z |
| publishDate | 2020-09-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-fb8162e9d0df4d94990e0f83ed02aa312023-11-20T12:08:09ZengMDPI AGCatalysts2073-43442020-09-0110998910.3390/catal10090989Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic AcidAmine Bourouina0Alexis Oswald1Valentin Lido2Lu Dong3Franck Rataboul4Laurent Djakovitch5Claude de Bellefon6Valérie Meille7Univ Lyon, CNRS, Université Claude-Bernard Lyon 1, CPE-Lyon, LGPC, F-69616 Villeurbanne, FranceUniv Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON, F-69626 Villeurbanne, FranceUniv Lyon, CNRS, Université Claude-Bernard Lyon 1, CPE-Lyon, LGPC, F-69616 Villeurbanne, FranceUniv Lyon, CNRS, Université Claude-Bernard Lyon 1, CPE-Lyon, LGPC, F-69616 Villeurbanne, FranceUniv Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON, F-69626 Villeurbanne, FranceUniv Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON, F-69626 Villeurbanne, FranceUniv Lyon, CNRS, Université Claude-Bernard Lyon 1, CPE-Lyon, LGPC, F-69616 Villeurbanne, FranceUniv Lyon, CNRS, Université Claude-Bernard Lyon 1, CPE-Lyon, LGPC, F-69616 Villeurbanne, FranceThis article presents an experimental kinetic study of the Suzuki–Miyaura reaction of 4-iodoacetophenone with phenylboronic acid catalyzed by the Herrmann–Beller palladacycle. This catalyst, together with the solvent (ethanol) and the base (sodium methylate), were chosen to ensure catalyst stability and reactants solubility all along the reaction. Based on the study of initial reaction rates, a quasi-first-order was found for 4-iodoacetophenone with a first-order dependence on the initial concentration of palladium. A zero-order was found for the base and the phenylboronic acid. The oxidative addition step of the mechanism was thus considered as the rate determining step. A global rate law was derived and validated quantitatively. A global activation energy, with an average value of ca. 63 kJ/mol was determined.https://www.mdpi.com/2073-4344/10/9/989kineticsSuzuki–Miyaurapalladacycleactivation energyC–C coupling |
| spellingShingle | Amine Bourouina Alexis Oswald Valentin Lido Lu Dong Franck Rataboul Laurent Djakovitch Claude de Bellefon Valérie Meille Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid Catalysts kinetics Suzuki–Miyaura palladacycle activation energy C–C coupling |
| title | Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid |
| title_full | Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid |
| title_fullStr | Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid |
| title_full_unstemmed | Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid |
| title_short | Kinetic Study of the Herrmann–Beller Palladacycle-Catalyzed Suzuki–Miyaura Coupling of 4-Iodoacetophenone and Phenylboronic Acid |
| title_sort | kinetic study of the herrmann beller palladacycle catalyzed suzuki miyaura coupling of 4 iodoacetophenone and phenylboronic acid |
| topic | kinetics Suzuki–Miyaura palladacycle activation energy C–C coupling |
| url | https://www.mdpi.com/2073-4344/10/9/989 |
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