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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...

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Autores principales: Kubota, Koji, Baba, Emiru, Seo, Tamae, Ishiyama, Tatsuo, Ito, Hajime
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
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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.
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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
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