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Visible light-promoted iron-catalyzed C(sp2)-C(sp3) Kumada cross-coupling in flow

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Wei_2019_ACIE_Visible_CC.pdf (2.619Mb)
Date
05/09/2019
Author
Wei, Xiao-Jing
Abdiaj, Irini
Sambiagio, Carlo
Li, Chenfei
Zysman-Colman, Eli
Alcázar, Jesús
Noël, Timothy
Funder
EPSRC
Grant ID
EP/M02105X/1
Keywords
Cross-coupling
Iron catalysis
Photocatalysis
Kumada coupling
Flow chemistry
QD Chemistry
DAS
BDC
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Abstract
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.
Citation
Wei , X-J , Abdiaj , I , Sambiagio , C , Li , C , Zysman-Colman , E , Alcázar , J & Noël , T 2019 , ' Visible light-promoted iron-catalyzed C(sp 2 )-C(sp 3 ) Kumada cross-coupling in flow ' , Angewandte Chemie International Edition , vol. 58 , no. 37 , pp. 13030-13034 . https://doi.org/10.1002/anie.201906462
Publication
Angewandte Chemie International Edition
Status
Peer reviewed
DOI
https://doi.org/10.1002/anie.201906462
ISSN
1433-7851
Type
Journal article
Rights
Copyright © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution‐NonCommercial License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
Description
X.-J.W., I.A., J.A., and T.N. would like to acknowledge the European Union for a Marie Curie ITN Grant (Photo4Future, Grant No. 641861). C.S. acknowledges the European Union for a Marie Curie European post-doctoral fellowship (FlowAct, Grant No. 794072). We would like to thank the Engineering and Physical Sciences Research Council for financial support (EP/M02105X/1). C. L. thanks the Prof. & Mrs Purdie Bequests Scholarship and AstraZeneca for his PhD Studentship.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/18092

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