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Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow

Transition‐metal‐catalyzed cross‐coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal...

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Autores principales: Deng, Yuchao, Wei, Xiao‐Jing, Wang, Xiao, Sun, Yuhan, Noël, Timothy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6900226/
https://www.ncbi.nlm.nih.gov/pubmed/31573119
http://dx.doi.org/10.1002/chem.201904480
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author Deng, Yuchao
Wei, Xiao‐Jing
Wang, Xiao
Sun, Yuhan
Noël, Timothy
author_facet Deng, Yuchao
Wei, Xiao‐Jing
Wang, Xiao
Sun, Yuhan
Noël, Timothy
author_sort Deng, Yuchao
collection PubMed
description Transition‐metal‐catalyzed cross‐coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron‐based cross‐coupling reaction that enables the formation of Csp−Csp(3) and Csp(2)−Csp(3) bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity.
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spelling pubmed-69002262019-12-20 Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow Deng, Yuchao Wei, Xiao‐Jing Wang, Xiao Sun, Yuhan Noël, Timothy Chemistry Communications Transition‐metal‐catalyzed cross‐coupling chemistry can be regarded as one of the most powerful protocols to construct carbon–carbon bonds. While the field is still dominated by palladium catalysis, there is an increasing interest to develop protocols that utilize cheaper and more sustainable metal sources. Herein, we report a selective, practical, and fast iron‐based cross‐coupling reaction that enables the formation of Csp−Csp(3) and Csp(2)−Csp(3) bonds. In a telescoped flow process, the reaction can be combined with the Grignard reagent synthesis. Moreover, flow allows the use of a supporting ligand to be avoided without eroding the reaction selectivity. John Wiley and Sons Inc. 2019-10-22 2019-11-18 /pmc/articles/PMC6900226/ /pubmed/31573119 http://dx.doi.org/10.1002/chem.201904480 Text en © 2019 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
Deng, Yuchao
Wei, Xiao‐Jing
Wang, Xiao
Sun, Yuhan
Noël, Timothy
Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title_full Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title_fullStr Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title_full_unstemmed Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title_short Iron‐Catalyzed Cross‐Coupling of Alkynyl and Styrenyl Chlorides with Alkyl Grignard Reagents in Batch and Flow
title_sort iron‐catalyzed cross‐coupling of alkynyl and styrenyl chlorides with alkyl grignard reagents in batch and flow
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6900226/
https://www.ncbi.nlm.nih.gov/pubmed/31573119
http://dx.doi.org/10.1002/chem.201904480
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