Cargando…
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...
Autores principales: | , , , , , , |
---|---|
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 |
_version_ | 1783455724709347328 |
---|---|
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. |
format | Online Article Text |
id | pubmed-6771604 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT weixiaojing visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT abdiajirini visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT sambiagiocarlo visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT lichenfei visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT zysmancolmaneli visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT alcazarjesus visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow AT noeltimothy visiblelightpromotedironcatalyzedcsp2csp3kumadacrosscouplinginflow |