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Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow

A continuous‐flow, visible‐light‐promoted method has been developed to overcome the limitations of iron‐catalyzed Kumada–Corriu cross‐coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at r...

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Detalles Bibliográficos
Autores principales: Wei, Xiao‐Jing, Abdiaj, Irini, Sambiagio, Carlo, Li, Chenfei, Zysman‐Colman, Eli, Alcázar, Jesús, 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/PMC6771604/
https://www.ncbi.nlm.nih.gov/pubmed/31210010
http://dx.doi.org/10.1002/anie.201906462
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author Wei, Xiao‐Jing
Abdiaj, Irini
Sambiagio, Carlo
Li, Chenfei
Zysman‐Colman, Eli
Alcázar, Jesús
Noël, Timothy
author_facet Wei, Xiao‐Jing
Abdiaj, Irini
Sambiagio, Carlo
Li, Chenfei
Zysman‐Colman, Eli
Alcázar, Jesús
Noël, Timothy
author_sort Wei, Xiao‐Jing
collection PubMed
description A continuous‐flow, visible‐light‐promoted method has been developed to overcome the limitations of iron‐catalyzed Kumada–Corriu cross‐coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron‐catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application.
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spelling pubmed-67716042019-10-03 Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow Wei, Xiao‐Jing Abdiaj, Irini Sambiagio, Carlo Li, Chenfei Zysman‐Colman, Eli Alcázar, Jesús Noël, Timothy Angew Chem Int Ed Engl Communications A continuous‐flow, visible‐light‐promoted method has been developed to overcome the limitations of iron‐catalyzed Kumada–Corriu cross‐coupling reactions. A variety of strongly electron rich aryl chlorides, previously hardly reactive, could be efficiently coupled with aliphatic Grignard reagents at room temperature in high yields and within a few minutes’ residence time, considerably enhancing the applicability of this iron‐catalyzed reaction. The robustness of this protocol was demonstrated on a multigram scale, thus providing the potential for future pharmaceutical application. John Wiley and Sons Inc. 2019-07-11 2019-09-09 /pmc/articles/PMC6771604/ /pubmed/31210010 http://dx.doi.org/10.1002/anie.201906462 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-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Communications
Wei, Xiao‐Jing
Abdiaj, Irini
Sambiagio, Carlo
Li, Chenfei
Zysman‐Colman, Eli
Alcázar, Jesús
Noël, Timothy
Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title_full Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title_fullStr Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title_full_unstemmed Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title_short Visible‐Light‐Promoted Iron‐Catalyzed C(sp(2))–C(sp(3)) Kumada Cross‐Coupling in Flow
title_sort visible‐light‐promoted iron‐catalyzed c(sp(2))–c(sp(3)) kumada cross‐coupling in flow
topic Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6771604/
https://www.ncbi.nlm.nih.gov/pubmed/31210010
http://dx.doi.org/10.1002/anie.201906462
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