Visible‐Light‐Promoted Iron‐Catalyzed C(sp2)–C(sp3) 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...

Full description

Saved in:
Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-09, Vol.58 (37), p.13030-13034
Main Authors: Wei, Xiao‐Jing, Abdiaj, Irini, Sambiagio, Carlo, Li, Chenfei, Zysman‐Colman, Eli, Alcázar, Jesús, Noël, Timothy
Format: Article
Language:English
Subjects:
Aliphatic compounds
Aromatic compounds
Chemical reactions
Communication
Communications
Coupling
cross-coupling
flow chemistry
Iron
iron catalysis
Kumada coupling
photocatalysis
Reagents
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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. Iron shines in the spotlight: An accelerated, visible‐light‐promoted iron‐catalyzed Kumada cross‐coupling reaction enabled the high‐yielding coupling of electron‐rich aryl chlorides with aliphatic Grignard reagents, which is normally very challenging in the absence of light. The use of flow conditions enabled full conversion in a matter of minutes and scalability to multigram amounts of substrates and products.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201906462