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Iron-catalysed cross-coupling of organolithium compounds with organic halides

In past decades, catalytic cross-coupling reactions between organic halides and organometallic reagents to construct carbon–carbon bond have achieved a tremendous progress. However, organolithium reagents have rarely been used in cross-coupling reactions, due mainly to their high reactivity. Another...

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Autores principales: Jia, Zhenhua, Liu, Qiang, Peng, Xiao-Shui, Wong, Henry N. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Nature Publishing Group 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4748252/
https://www.ncbi.nlm.nih.gov/pubmed/26847602
http://dx.doi.org/10.1038/ncomms10614
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author Jia, Zhenhua
Liu, Qiang
Peng, Xiao-Shui
Wong, Henry N. C.
author_facet Jia, Zhenhua
Liu, Qiang
Peng, Xiao-Shui
Wong, Henry N. C.
author_sort Jia, Zhenhua
collection PubMed
description In past decades, catalytic cross-coupling reactions between organic halides and organometallic reagents to construct carbon–carbon bond have achieved a tremendous progress. However, organolithium reagents have rarely been used in cross-coupling reactions, due mainly to their high reactivity. Another limitation of this transformation using organolithium reagents is how to control reactivity with excellent selectivity. Although palladium catalysis has been applied in this field recently, the development of an approach to replace catalytic systems of noble metals with nonprecious metals is currently in high demand. Herein, we report an efficient synthetic protocol involving iron-catalysed cross-coupling reactions employing organolithium compounds as key coupling partners to unite aryl, alkyl and benzyl fragments and also disclose an efficient iron-catalysed release-capture ethylene coupling with isopropyllithium.
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spelling pubmed-47482522016-02-24 Iron-catalysed cross-coupling of organolithium compounds with organic halides Jia, Zhenhua Liu, Qiang Peng, Xiao-Shui Wong, Henry N. C. Nat Commun Article In past decades, catalytic cross-coupling reactions between organic halides and organometallic reagents to construct carbon–carbon bond have achieved a tremendous progress. However, organolithium reagents have rarely been used in cross-coupling reactions, due mainly to their high reactivity. Another limitation of this transformation using organolithium reagents is how to control reactivity with excellent selectivity. Although palladium catalysis has been applied in this field recently, the development of an approach to replace catalytic systems of noble metals with nonprecious metals is currently in high demand. Herein, we report an efficient synthetic protocol involving iron-catalysed cross-coupling reactions employing organolithium compounds as key coupling partners to unite aryl, alkyl and benzyl fragments and also disclose an efficient iron-catalysed release-capture ethylene coupling with isopropyllithium. Nature Publishing Group 2016-02-05 /pmc/articles/PMC4748252/ /pubmed/26847602 http://dx.doi.org/10.1038/ncomms10614 Text en Copyright © 2016, 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
Jia, Zhenhua
Liu, Qiang
Peng, Xiao-Shui
Wong, Henry N. C.
Iron-catalysed cross-coupling of organolithium compounds with organic halides
title Iron-catalysed cross-coupling of organolithium compounds with organic halides
title_full Iron-catalysed cross-coupling of organolithium compounds with organic halides
title_fullStr Iron-catalysed cross-coupling of organolithium compounds with organic halides
title_full_unstemmed Iron-catalysed cross-coupling of organolithium compounds with organic halides
title_short Iron-catalysed cross-coupling of organolithium compounds with organic halides
title_sort iron-catalysed cross-coupling of organolithium compounds with organic halides
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4748252/
https://www.ncbi.nlm.nih.gov/pubmed/26847602
http://dx.doi.org/10.1038/ncomms10614
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