Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities
We reported in this study the hydroboration of enamides in methanol at room temperature catalyzed by copper complexes. Under such conditions, a Gram-scale reaction with a high yield was also completed. Hydroboration of 3-methylene, 2-(alkyl and phenylisoindolin-1-one 5 with bis(pinacolato)diboron yi...
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| Format: | Article |
| Language: | English |
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Wiley
2022-01-01
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| Series: | Journal of Chemistry |
| Online Access: | http://dx.doi.org/10.1155/2022/6577185 |
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| author | Hamida Jelali Waleed Koko Sadeq M. Al-Hazmy Lamjed Mansour Jameel Al-Tamimi Eric Deniau Mathieu Sauthier Khaireddine Dridi Naceur Hamdi |
| author_facet | Hamida Jelali Waleed Koko Sadeq M. Al-Hazmy Lamjed Mansour Jameel Al-Tamimi Eric Deniau Mathieu Sauthier Khaireddine Dridi Naceur Hamdi |
| author_sort | Hamida Jelali |
| collection | DOAJ |
| description | We reported in this study the hydroboration of enamides in methanol at room temperature catalyzed by copper complexes. Under such conditions, a Gram-scale reaction with a high yield was also completed. Hydroboration of 3-methylene, 2-(alkyl and phenylisoindolin-1-one 5 with bis(pinacolato)diboron yields the respective compounds 6 in good yields with high-to-moderate enantioselectivity (58% ee). Furthermore, the antimicrobial properties of the synthesized compounds were tested against four indicator microorganisms: the two Gram-positive bacteria L. monocytogenes ATCC 1911 and S. aureus ATCC 6538, the Gram-negative bacterium S. typhimurium ATCC 14028, and the fungus C. albicans (ATCC 90028). The MIC values of compounds 5-6 range from 0.312 to 2.5 (μg/mL) against L. monocytogenes, from 2.1 to 0.136 (μg/mL) against S. aureus, and from 0.126 to 0.923 (μg/mL) against S. typhimurium. |
| format | Article |
| id | doaj-art-b2175d2d32954961a1429a6e32c67039 |
| institution | Kabale University |
| issn | 2090-9071 |
| language | English |
| publishDate | 2022-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Journal of Chemistry |
| spelling | doaj-art-b2175d2d32954961a1429a6e32c670392025-02-03T10:59:56ZengWileyJournal of Chemistry2090-90712022-01-01202210.1155/2022/6577185Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial ActivitiesHamida Jelali0Waleed Koko1Sadeq M. Al-Hazmy2Lamjed Mansour3Jameel Al-Tamimi4Eric Deniau5Mathieu Sauthier6Khaireddine Dridi7Naceur Hamdi8Research Laboratory of Environmental Sciences and Technologies (LR16ES09)Department of Science LaboratoriesDepartment of ChemistryDepartment of ZoologyDepartment of ZoologyUniversity of LilleUniversity of LilleDepartment of ChemistryDepartment of ChemistryWe reported in this study the hydroboration of enamides in methanol at room temperature catalyzed by copper complexes. Under such conditions, a Gram-scale reaction with a high yield was also completed. Hydroboration of 3-methylene, 2-(alkyl and phenylisoindolin-1-one 5 with bis(pinacolato)diboron yields the respective compounds 6 in good yields with high-to-moderate enantioselectivity (58% ee). Furthermore, the antimicrobial properties of the synthesized compounds were tested against four indicator microorganisms: the two Gram-positive bacteria L. monocytogenes ATCC 1911 and S. aureus ATCC 6538, the Gram-negative bacterium S. typhimurium ATCC 14028, and the fungus C. albicans (ATCC 90028). The MIC values of compounds 5-6 range from 0.312 to 2.5 (μg/mL) against L. monocytogenes, from 2.1 to 0.136 (μg/mL) against S. aureus, and from 0.126 to 0.923 (μg/mL) against S. typhimurium.http://dx.doi.org/10.1155/2022/6577185 |
| spellingShingle | Hamida Jelali Waleed Koko Sadeq M. Al-Hazmy Lamjed Mansour Jameel Al-Tamimi Eric Deniau Mathieu Sauthier Khaireddine Dridi Naceur Hamdi Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities Journal of Chemistry |
| title | Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities |
| title_full | Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities |
| title_fullStr | Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities |
| title_full_unstemmed | Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities |
| title_short | Copper-Catalyzed Hydroboration of Enamides with Bis(pinacolato)diboron: Promising Agents with Antimicrobial Activities |
| title_sort | copper catalyzed hydroboration of enamides with bis pinacolato diboron promising agents with antimicrobial activities |
| url | http://dx.doi.org/10.1155/2022/6577185 |
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