Ionic liquid-promoted green synthesis of biologically relevant diaryl thioethers
| Title: | Ionic liquid-promoted green synthesis of biologically relevant diaryl thioethers |
|---|---|
| Authors: | Doretta Cuffaro, Felicia D’Andrea, Andrea Mezzetta, Lorenzo Guazzelli, Cinzia Chiappe, Elisa Nuti, Armando Rossello |
| Source: | Green Chemistry Letters and Reviews, Vol 13, Iss 4, Pp 295-302 (2020) |
| Publisher Information: | Taylor & Francis Group, 2020. |
| Publication Year: | 2020 |
| Collection: | LCC:Science LCC:Chemistry |
| Subject Terms: | ionic liquids, diaryl thioethers, ullmann reaction, suzuki cross-coupling, microwave irradiation, Science, Chemistry, QD1-999 |
| More Details: | This study reports an ionic liquid (IL) promoted green method to obtain diaryl thioethers useful as key intermediates for the synthesis of matrix metalloproteinase (MMP) inhibitors. The synthetic pathway includes a sequential Ullmann reaction and Suzuki cross-coupling. The Ullmann conditions were optimized as regards the catalyst, the ionic liquid, reaction time, and temperature. Under optimal conditions (1-butyl-3-methylimidazolium bromide ([BMIM]Br) as solvent; catalyst, Cu; base, K2CO3; reaction time, 22 h; reaction temperature, 150°C) the aryl iodide conversion was 95%. The Suzuki cross-coupling was conducted in 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM]BF4) at 110°C, using Pd(PPh3)4 as catalyst and Na2CO3 as base. For both reactions, a combination of ILs with microwave (MW) irradiation determined a substantial improvement of reaction time and yields compared to conventional heating. This multi-step process reduces reaction times and removes organic solvents providing a more eco-friendly alternative for the synthesis of important pharmaceutical building blocks. |
| Document Type: | article |
| File Description: | electronic resource |
| Language: | English |
| ISSN: | 1751-8253 1751-7192 17518253 |
| Relation: | https://doaj.org/toc/1751-8253; https://doaj.org/toc/1751-7192 |
| DOI: | 10.1080/17518253.2020.1831082 |
| Access URL: | https://doaj.org/article/19c2c7b13d6e4584b2d683c0f5f68798 |
| Accession Number: | edsdoj.19c2c7b13d6e4584b2d683c0f5f68798 |
| Database: | Directory of Open Access Journals |
| ISSN: | 17518253 17517192 |
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| DOI: | 10.1080/17518253.2020.1831082 |
| Published in: | Green Chemistry Letters and Reviews |
| Language: | English |