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Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis

The widespread adoption of earth-abundant metal catalysis lags behind that of the second- and third-row transition metals due to the often challenging practical requirements needed to generate the active low oxidation-state catalysts. Here we report the development of a single endogenous activation...

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Autores principales: Agahi, Riaz, Challinor, Amy J., Dunne, Joanne, Docherty, Jamie H., Carter, Neil B., Thomas, Stephen P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6524663/
https://www.ncbi.nlm.nih.gov/pubmed/31183059
http://dx.doi.org/10.1039/c8sc05391j
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author Agahi, Riaz
Challinor, Amy J.
Dunne, Joanne
Docherty, Jamie H.
Carter, Neil B.
Thomas, Stephen P.
author_facet Agahi, Riaz
Challinor, Amy J.
Dunne, Joanne
Docherty, Jamie H.
Carter, Neil B.
Thomas, Stephen P.
author_sort Agahi, Riaz
collection PubMed
description The widespread adoption of earth-abundant metal catalysis lags behind that of the second- and third-row transition metals due to the often challenging practical requirements needed to generate the active low oxidation-state catalysts. Here we report the development of a single endogenous activation protocol across five reaction classes using both iron- and cobalt pre-catalysts. This simple catalytic manifold uses commercially available, bench-stable iron- or cobalt tetrafluoroborate salts to perform regiodivergent alkene and alkyne hydrosilylation, 1,3-diene hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation. The activation protocol proceeds by fluoride dissociation from the counterion, in situ formation of a hydridic activator and generation of a low oxidation-state catalyst.
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spelling pubmed-65246632019-06-10 Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis Agahi, Riaz Challinor, Amy J. Dunne, Joanne Docherty, Jamie H. Carter, Neil B. Thomas, Stephen P. Chem Sci Chemistry The widespread adoption of earth-abundant metal catalysis lags behind that of the second- and third-row transition metals due to the often challenging practical requirements needed to generate the active low oxidation-state catalysts. Here we report the development of a single endogenous activation protocol across five reaction classes using both iron- and cobalt pre-catalysts. This simple catalytic manifold uses commercially available, bench-stable iron- or cobalt tetrafluoroborate salts to perform regiodivergent alkene and alkyne hydrosilylation, 1,3-diene hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation. The activation protocol proceeds by fluoride dissociation from the counterion, in situ formation of a hydridic activator and generation of a low oxidation-state catalyst. Royal Society of Chemistry 2019-04-08 /pmc/articles/PMC6524663/ /pubmed/31183059 http://dx.doi.org/10.1039/c8sc05391j 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
Agahi, Riaz
Challinor, Amy J.
Dunne, Joanne
Docherty, Jamie H.
Carter, Neil B.
Thomas, Stephen P.
Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title_full Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title_fullStr Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title_full_unstemmed Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title_short Regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and C–H borylation using counterion activated earth-abundant metal catalysis
title_sort regiodivergent hydrosilylation, hydrogenation, [2π + 2π]-cycloaddition and c–h borylation using counterion activated earth-abundant metal catalysis
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6524663/
https://www.ncbi.nlm.nih.gov/pubmed/31183059
http://dx.doi.org/10.1039/c8sc05391j
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