Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling
In this work, for the first time, naphthalene (NA)-based polymers were synthesized by one-stage Friedel–Crafts crosslinking. The influence of NA functionalization by -OH, -SO<sub>3</sub>H, and -NO<sub>2</sub> groups on the polymers’ porosity and distribution of the catalytica...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2023-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/13/4938 |
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| author | Elena S. Bakhvalova Alexey V. Bykov Mariia E. Markova Yury V. Lugovoy Alexander I. Sidorov Vladimir P. Molchanov Mikhail G. Sulman Lioubov Kiwi-Minsker Linda Z. Nikoshvili |
| author_facet | Elena S. Bakhvalova Alexey V. Bykov Mariia E. Markova Yury V. Lugovoy Alexander I. Sidorov Vladimir P. Molchanov Mikhail G. Sulman Lioubov Kiwi-Minsker Linda Z. Nikoshvili |
| author_sort | Elena S. Bakhvalova |
| collection | DOAJ |
| description | In this work, for the first time, naphthalene (NA)-based polymers were synthesized by one-stage Friedel–Crafts crosslinking. The influence of NA functionalization by -OH, -SO<sub>3</sub>H, and -NO<sub>2</sub> groups on the polymers’ porosity and distribution of the catalytically active phase (Pd) was studied. Synthesized catalytic systems containing 1 wt.% of Pd either in the form of Pd(II) species or Pd(0) nanoparticles supported on NA-based polymers were tested in a model reaction of Suzuki cross-coupling between 4-bromoanisole and phenylboronic acid under mild reaction conditions (60 °C, ethanol-water mixture as a solvent). These novel catalysts demonstrated high efficiency with more than 95% of 4-bromoanisole conversion and high selectivity (>97%) for the target 4-methoxybiphenyl. |
| first_indexed | 2024-03-11T01:34:08Z |
| format | Article |
| id | doaj.art-5c5aa906bc8a41c7a6ce2946473e028e |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T01:34:08Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-5c5aa906bc8a41c7a6ce2946473e028e2023-11-18T17:05:43ZengMDPI AGMolecules1420-30492023-06-012813493810.3390/molecules28134938Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-CouplingElena S. Bakhvalova0Alexey V. Bykov1Mariia E. Markova2Yury V. Lugovoy3Alexander I. Sidorov4Vladimir P. Molchanov5Mikhail G. Sulman6Lioubov Kiwi-Minsker7Linda Z. Nikoshvili8Regional Technological Centre, Tver State University, Zhelyabova Str., 33, 170100 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaRegional Technological Centre, Tver State University, Zhelyabova Str., 33, 170100 Tver, RussiaDepartment of Biotechnology, Chemistry and Standardization, Tver State Technical University, A.Nikitina Str., 22, 170026 Tver, RussiaIn this work, for the first time, naphthalene (NA)-based polymers were synthesized by one-stage Friedel–Crafts crosslinking. The influence of NA functionalization by -OH, -SO<sub>3</sub>H, and -NO<sub>2</sub> groups on the polymers’ porosity and distribution of the catalytically active phase (Pd) was studied. Synthesized catalytic systems containing 1 wt.% of Pd either in the form of Pd(II) species or Pd(0) nanoparticles supported on NA-based polymers were tested in a model reaction of Suzuki cross-coupling between 4-bromoanisole and phenylboronic acid under mild reaction conditions (60 °C, ethanol-water mixture as a solvent). These novel catalysts demonstrated high efficiency with more than 95% of 4-bromoanisole conversion and high selectivity (>97%) for the target 4-methoxybiphenyl.https://www.mdpi.com/1420-3049/28/13/4938naphthaleneFriedel–Crafts crosslinkingsulfonationnitrationpalladiumSuzuki cross-coupling |
| spellingShingle | Elena S. Bakhvalova Alexey V. Bykov Mariia E. Markova Yury V. Lugovoy Alexander I. Sidorov Vladimir P. Molchanov Mikhail G. Sulman Lioubov Kiwi-Minsker Linda Z. Nikoshvili Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling Molecules naphthalene Friedel–Crafts crosslinking sulfonation nitration palladium Suzuki cross-coupling |
| title | Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling |
| title_full | Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling |
| title_fullStr | Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling |
| title_full_unstemmed | Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling |
| title_short | Naphthalene-Based Polymers as Catalytic Supports for Suzuki Cross-Coupling |
| title_sort | naphthalene based polymers as catalytic supports for suzuki cross coupling |
| topic | naphthalene Friedel–Crafts crosslinking sulfonation nitration palladium Suzuki cross-coupling |
| url | https://www.mdpi.com/1420-3049/28/13/4938 |
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