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Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry

The Suzuki–Miyaura cross-coupling reaction is one of the most reliable methods for the construction of carbon–carbon bonds in solution. However, examples for the corresponding solid-state cross-coupling reactions remain scarce. Herein, we report the first broadly applicable mechanochemical protocol...

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Detalles Bibliográficos
Autores principales: Seo, Tamae, Ishiyama, Tatsuo, Kubota, Koji, Ito, Hajime
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6836942/
https://www.ncbi.nlm.nih.gov/pubmed/31857886
http://dx.doi.org/10.1039/c9sc02185j
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author Seo, Tamae
Ishiyama, Tatsuo
Kubota, Koji
Ito, Hajime
author_facet Seo, Tamae
Ishiyama, Tatsuo
Kubota, Koji
Ito, Hajime
author_sort Seo, Tamae
collection PubMed
description The Suzuki–Miyaura cross-coupling reaction is one of the most reliable methods for the construction of carbon–carbon bonds in solution. However, examples for the corresponding solid-state cross-coupling reactions remain scarce. Herein, we report the first broadly applicable mechanochemical protocol for a solid-state palladium-catalyzed organoboron cross-coupling reaction using an olefin additive. Compared to previous studies, the newly developed protocol shows a substantially broadened substrate scope. Our mechanistic data suggest that olefin additives might act as dispersants for the palladium-based catalyst to suppress higher aggregation of the nanoparticles, and also as stabilizer for the active monomeric Pd(0) species, thus facilitating these challenging solid-state C–C bond forming cross-coupling reactions.
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spelling pubmed-68369422019-12-19 Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry Seo, Tamae Ishiyama, Tatsuo Kubota, Koji Ito, Hajime Chem Sci Chemistry The Suzuki–Miyaura cross-coupling reaction is one of the most reliable methods for the construction of carbon–carbon bonds in solution. However, examples for the corresponding solid-state cross-coupling reactions remain scarce. Herein, we report the first broadly applicable mechanochemical protocol for a solid-state palladium-catalyzed organoboron cross-coupling reaction using an olefin additive. Compared to previous studies, the newly developed protocol shows a substantially broadened substrate scope. Our mechanistic data suggest that olefin additives might act as dispersants for the palladium-based catalyst to suppress higher aggregation of the nanoparticles, and also as stabilizer for the active monomeric Pd(0) species, thus facilitating these challenging solid-state C–C bond forming cross-coupling reactions. Royal Society of Chemistry 2019-07-22 /pmc/articles/PMC6836942/ /pubmed/31857886 http://dx.doi.org/10.1039/c9sc02185j Text en This journal is © The Royal Society of Chemistry 2019 http://creativecommons.org/licenses/by-nc/3.0/ This article is freely available. This article is licensed under a Creative Commons Attribution Non Commercial 3.0 Unported Licence (CC BY-NC 3.0)
spellingShingle Chemistry
Seo, Tamae
Ishiyama, Tatsuo
Kubota, Koji
Ito, Hajime
Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title_full Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title_fullStr Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title_full_unstemmed Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title_short Solid-state Suzuki–Miyaura cross-coupling reactions: olefin-accelerated C–C coupling using mechanochemistry
title_sort solid-state suzuki–miyaura cross-coupling reactions: olefin-accelerated c–c coupling using mechanochemistry
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6836942/
https://www.ncbi.nlm.nih.gov/pubmed/31857886
http://dx.doi.org/10.1039/c9sc02185j
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AT kubotakoji solidstatesuzukimiyauracrosscouplingreactionsolefinacceleratedcccouplingusingmechanochemistry
AT itohajime solidstatesuzukimiyauracrosscouplingreactionsolefinacceleratedcccouplingusingmechanochemistry