A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates

The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross‐coupling of benzyl bromides with aryl bora...

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Detalles Bibliográficos
Autores principales: Procter, Richard J., Dunsford, Jay J., Rushworth, Philip J., Hulcoop, David G., Layfield, Richard A., Ingleson, Michael J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2017
Materias:
Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5915750/
https://www.ncbi.nlm.nih.gov/pubmed/28960610
http://dx.doi.org/10.1002/chem.201704170
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author Procter, Richard J.
Dunsford, Jay J.
Rushworth, Philip J.
Hulcoop, David G.
Layfield, Richard A.
Ingleson, Michael J.
author_facet Procter, Richard J.
Dunsford, Jay J.
Rushworth, Philip J.
Hulcoop, David G.
Layfield, Richard A.
Ingleson, Michael J.
author_sort Procter, Richard J.
collection PubMed
description The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross‐coupling of benzyl bromides with aryl borates is catalyzed by ZnBr(2), in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross‐coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity.
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spelling pubmed-59157502018-05-02 A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates Procter, Richard J. Dunsford, Jay J. Rushworth, Philip J. Hulcoop, David G. Layfield, Richard A. Ingleson, Michael J. Chemistry Communications The Suzuki–Miyaura (SM) reaction is one of the most important methods for C−C bond formation in chemical synthesis. In this communication, we show for the first time that the low toxicity, inexpensive element zinc is able to catalyze SM reactions. The cross‐coupling of benzyl bromides with aryl borates is catalyzed by ZnBr(2), in a process that is free from added ligand, and is compatible with a range of functionalized benzyl bromides and arylboronic acid pinacol esters. Initial mechanistic investigations indicate that the selective in situ formation of triaryl zincates is crucial to promote selective cross‐coupling reactivity, which is facilitated by employing an arylborate of optimal nucleophilicity. John Wiley and Sons Inc. 2017-10-19 2017-11-13 /pmc/articles/PMC5915750/ /pubmed/28960610 http://dx.doi.org/10.1002/chem.201704170 Text en © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Communications
Procter, Richard J.
Dunsford, Jay J.
Rushworth, Philip J.
Hulcoop, David G.
Layfield, Richard A.
Ingleson, Michael J.
A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title_full A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title_fullStr A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title_full_unstemmed A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title_short A Zinc Catalyzed C(sp(3))−C(sp(2)) Suzuki–Miyaura Cross‐Coupling Reaction Mediated by Aryl‐Zincates
title_sort zinc catalyzed c(sp(3))−c(sp(2)) suzuki–miyaura cross‐coupling reaction mediated by aryl‐zincates
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5915750/
https://www.ncbi.nlm.nih.gov/pubmed/28960610
http://dx.doi.org/10.1002/chem.201704170
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