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

Xiao-Jing Wei; Irini Abdiaj; Carlo Sambiagio; Chenfei Li; Eli Zysman-Colman; Jesús Alcázar; Timothy Noël

doi:10.1002/anie.201906462

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

Xiao-Jing Wei, Irini Abdiaj, Carlo Sambiagio, Chenfei Li, Eli Zysman-Colman, Jesús Alcázar, Timothy Noël

Research output: Contribution to journal › Article › peer-review

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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.

Original language	English
Pages (from-to)	13030-13034
Number of pages	6
Journal	Angewandte Chemie International Edition
Volume	58
Issue number	37
Early online date	11 Jul 2019
DOIs	https://doi.org/10.1002/anie.201906462
Publication status	Published - 5 Sept 2019

Keywords

Cross-coupling
Iron catalysis
Photocatalysis
Kumada coupling
Flow chemistry

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10.1002/anie.201906462Licence: CC BY-NC

Wei_2019_ACIE_Visible_CC
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.
Final published version, 2.62 MBLicence: CC BY-NC

Blue-Emitting Phospors: Blue-emitting Phosphors for Solid State Lighting Applications
Zysman-Colman, E. (PI)
EPSRC
1/06/15 → 30/09/19
Project: Standard

Eli Zysman-Colman
- eli.zysman-colmanst-andrews.acuk
- School of Chemistry - Director of Impact, Professor of Optoelectronic Materials
- Centre for Energy Ethics
- Organic Semiconductor Centre
- EaSTCHEM
Person: Academic

Visible-Light-Promoted Iron-Catalyzed Csp2-Csp3Kumada Cross-Coupling in Flow (dataset)
Wei, X.-J. (Creator), Abdiaj, I. (Creator), Sambiagio, C. (Creator), Li, C. (Creator), Zysman-Colman, E. (Creator), Alcázar, J. (Creator) & Noël, T. (Creator), University of St Andrews, 20 Jun 2019
DOI: 10.17630/d726b2fb-17e0-4f10-b6e2-2da3e4ad49a3
Dataset

File

Cite this

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

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{\textquoteright} 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.",

keywords = "Cross-coupling, Iron catalysis, Photocatalysis, Kumada coupling, Flow chemistry",

author = "Xiao-Jing Wei and Irini Abdiaj and Carlo Sambiagio and Chenfei Li and Eli Zysman-Colman and Jes{\'u}s Alc{\'a}zar and Timothy No{\"e}l",

note = "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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month = sep,

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doi = "10.1002/anie.201906462",

language = "English",

volume = "58",

pages = "13030--13034",

journal = "Angewandte Chemie International Edition",

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TY - JOUR

T1 - Visible light-promoted iron-catalyzed C(sp2)-C(sp3) Kumada cross-coupling in flow

AU - Wei, Xiao-Jing

AU - Abdiaj, Irini

AU - Sambiagio, Carlo

AU - Li, Chenfei

AU - Zysman-Colman, Eli

AU - Alcázar, Jesús

AU - Noël, Timothy

N1 - 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.

PY - 2019/9/5

Y1 - 2019/9/5

N2 - 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.

AB - 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.

KW - Cross-coupling

KW - Iron catalysis

KW - Photocatalysis

KW - Kumada coupling

KW - Flow chemistry

U2 - 10.1002/anie.201906462

DO - 10.1002/anie.201906462

M3 - Article

SN - 1433-7851

VL - 58

SP - 13030

EP - 13034

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

IS - 37

ER -

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

Abstract

Keywords

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Projects

Blue-Emitting Phospors: Blue-emitting Phosphors for Solid State Lighting Applications

Profiles

Eli Zysman-Colman

Datasets

Visible-Light-Promoted Iron-Catalyzed Csp2-Csp3Kumada Cross-Coupling in Flow (dataset)

Cite this

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