Cargando…
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...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Beilstein-Institut
2022
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344555/ https://www.ncbi.nlm.nih.gov/pubmed/35957749 http://dx.doi.org/10.3762/bjoc.18.86 |
_version_ | 1784761245119807488 |
---|---|
author | Kubota, Koji Baba, Emiru Seo, Tamae Ishiyama, Tatsuo Ito, Hajime |
author_facet | Kubota, Koji Baba, Emiru Seo, Tamae Ishiyama, Tatsuo Ito, Hajime |
author_sort | Kubota, Koji |
collection | PubMed |
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. |
format | Online Article Text |
id | pubmed-9344555 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2022 |
publisher | Beilstein-Institut |
record_format | MEDLINE/PubMed |
spelling | pubmed-93445552022-08-10 Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry Kubota, Koji Baba, Emiru Seo, Tamae Ishiyama, Tatsuo Ito, Hajime Beilstein J Org Chem Letter 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. Beilstein-Institut 2022-07-18 /pmc/articles/PMC9344555/ /pubmed/35957749 http://dx.doi.org/10.3762/bjoc.18.86 Text en Copyright © 2022, Kubota et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material. |
spellingShingle | Letter Kubota, Koji Baba, Emiru Seo, Tamae Ishiyama, Tatsuo Ito, Hajime Palladium-catalyzed solid-state borylation of aryl halides using mechanochemistry |
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 | Letter |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9344555/ https://www.ncbi.nlm.nih.gov/pubmed/35957749 http://dx.doi.org/10.3762/bjoc.18.86 |
work_keys_str_mv | AT kubotakoji palladiumcatalyzedsolidstateborylationofarylhalidesusingmechanochemistry AT babaemiru palladiumcatalyzedsolidstateborylationofarylhalidesusingmechanochemistry AT seotamae palladiumcatalyzedsolidstateborylationofarylhalidesusingmechanochemistry AT ishiyamatatsuo palladiumcatalyzedsolidstateborylationofarylhalidesusingmechanochemistry AT itohajime palladiumcatalyzedsolidstateborylationofarylhalidesusingmechanochemistry |