Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry
This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experime...
| Main Authors: | , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2022-07-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.18.86 |
| _version_ | 1818173892267606016 |
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| author | Koji Kubota Emiru Baba Tamae Seo Tatsuo Ishiyama Hajime Ito |
| author_facet | Koji Kubota Emiru Baba Tamae Seo Tatsuo Ishiyama Hajime Ito |
| author_sort | Koji Kubota |
| collection | DOAJ |
| description | This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experimental operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochemical conditions. |
| first_indexed | 2024-12-11T19:35:43Z |
| format | Article |
| id | doaj.art-1009edc495c640f59575e17c829ce250 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-11T19:35:43Z |
| publishDate | 2022-07-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-1009edc495c640f59575e17c829ce2502022-12-22T00:53:09ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972022-07-0118185586210.3762/bjoc.18.861860-5397-18-86Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistryKoji Kubota0Emiru Baba1Tamae Seo2Tatsuo Ishiyama3Hajime Ito4Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan Division of Applied Chemistry, Graduate School of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan This study describes the solid-state palladium-catalyzed cross-coupling between aryl halides and bis(pinacolato)diboron using ball milling. The reactions were completed within 10 min for most aryl halides to afford a variety of synthetically useful arylboronates in high yields. Notably, all experimental operations could be performed in air, and did not require the use of large amounts of dry and degassed organic solvents. The utility of this method was further demonstrated by gram-scale synthesis under solvent-free, mechanochemical conditions.https://doi.org/10.3762/bjoc.18.86ball millborylationcross-couplingmechanochemistrysolid-state reaction |
| spellingShingle | Koji Kubota Emiru Baba Tamae Seo Tatsuo Ishiyama Hajime Ito Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry Beilstein Journal of Organic Chemistry ball mill borylation cross-coupling mechanochemistry solid-state reaction |
| title | Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
| title_full | Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
| title_fullStr | Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
| title_full_unstemmed | Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
| title_short | Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
| title_sort | palladium catalyzed solid state borylation of aryl halides using mechanochemistry |
| topic | ball mill borylation cross-coupling mechanochemistry solid-state reaction |
| url | https://doi.org/10.3762/bjoc.18.86 |
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