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Kumada–Grignard-type biaryl couplings on water

Well-established, traditional Kumada cross-couplings involve preformed Grignard reagents in dry ethereal solvent that typically react, e.g., with aryl halides via Pd catalysis to afford products of net substitution. Therefore, in the work described, which appears to be counterintuitive, exposure of...

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Autores principales: Bhattacharjya, Anish, Klumphu, Piyatida, Lipshutz, Bruce H.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Pub. Group 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647940/
https://www.ncbi.nlm.nih.gov/pubmed/26084774
http://dx.doi.org/10.1038/ncomms8401
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author Bhattacharjya, Anish
Klumphu, Piyatida
Lipshutz, Bruce H.
author_facet Bhattacharjya, Anish
Klumphu, Piyatida
Lipshutz, Bruce H.
author_sort Bhattacharjya, Anish
collection PubMed
description Well-established, traditional Kumada cross-couplings involve preformed Grignard reagents in dry ethereal solvent that typically react, e.g., with aryl halides via Pd catalysis to afford products of net substitution. Therefore, in the work described, which appears to be counterintuitive, exposure of these same aromatic halides to catalytic amounts of Pd(II) and excess magnesium metal in pure water leads to symmetrical/unsymmetrical biaryls, indicative of a net Kumada-like biaryl coupling. Evidence is presented suggesting that Grignard reagents, formed in situ in water, may be involved.
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spelling pubmed-46479402015-12-02 Kumada–Grignard-type biaryl couplings on water Bhattacharjya, Anish Klumphu, Piyatida Lipshutz, Bruce H. Nat Commun Article Well-established, traditional Kumada cross-couplings involve preformed Grignard reagents in dry ethereal solvent that typically react, e.g., with aryl halides via Pd catalysis to afford products of net substitution. Therefore, in the work described, which appears to be counterintuitive, exposure of these same aromatic halides to catalytic amounts of Pd(II) and excess magnesium metal in pure water leads to symmetrical/unsymmetrical biaryls, indicative of a net Kumada-like biaryl coupling. Evidence is presented suggesting that Grignard reagents, formed in situ in water, may be involved. Nature Pub. Group 2015-06-18 /pmc/articles/PMC4647940/ /pubmed/26084774 http://dx.doi.org/10.1038/ncomms8401 Text en Copyright © 2015, Nature Publishing Group, a division of Macmillan Publishers Limited. All Rights Reserved. http://creativecommons.org/licenses/by/4.0/ This work is licensed under a Creative Commons Attribution 4.0 International License. The images or other third party material in this article are included in the article's Creative Commons license, unless indicated otherwise in the credit line; if the material is not included under the Creative Commons license, users will need to obtain permission from the license holder to reproduce the material. To view a copy of this license, visit http://creativecommons.org/licenses/by/4.0/
spellingShingle Article
Bhattacharjya, Anish
Klumphu, Piyatida
Lipshutz, Bruce H.
Kumada–Grignard-type biaryl couplings on water
title Kumada–Grignard-type biaryl couplings on water
title_full Kumada–Grignard-type biaryl couplings on water
title_fullStr Kumada–Grignard-type biaryl couplings on water
title_full_unstemmed Kumada–Grignard-type biaryl couplings on water
title_short Kumada–Grignard-type biaryl couplings on water
title_sort kumada–grignard-type biaryl couplings on water
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4647940/
https://www.ncbi.nlm.nih.gov/pubmed/26084774
http://dx.doi.org/10.1038/ncomms8401
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