Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling

Striking while the iron is hot: Cheap FeCl3 serves as the precatalyst for the direct cross‐coupling of aryl and alkyl halides that is based on the sequence of Grignard formation and subsequent cross‐coupling. This one‐pot reaction obviates preformation of hazardous Grignard compounds and limits the...

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Published inAngewandte Chemie (International ed.) Vol. 48; no. 3; pp. 607 - 610
Main Authors Czaplik, Waldemar Maximilian, Mayer, Matthias, Jacobi von Wangelin, Axel
Format Journal Article
LanguageEnglish
Published Weinheim Wiley-VCH Verlag 01.01.2009
WILEY‐VCH Verlag
Wiley
Subjects
Chemistry
Chemistry, Multidisciplinary
cross‐coupling
domino reactions
Grignard reactions
iron
Physical Sciences
Science & Technology
sustainable chemistry
Grignard reactions
HALIDES
MAGNESIUM
AMINATION
INORGANIC GRIGNARD-REAGENTS
domino reactions
cross-coupling
iron
sustainable chemistry
MECHANISMS
BETA-HYDROGENS
PROCESS SAFETY
Online AccessGet full text

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Abstract Striking while the iron is hot: Cheap FeCl3 serves as the precatalyst for the direct cross‐coupling of aryl and alkyl halides that is based on the sequence of Grignard formation and subsequent cross‐coupling. This one‐pot reaction obviates preformation of hazardous Grignard compounds and limits the amount of reactive organomagnesium intermediates to low quasi‐stationary concentrations. TMEDA=N,N,N′,N′‐tetramethylethylenediamine.
AbstractList Striking while the iron is hot: Cheap FeCl3 serves as the precatalyst for the direct cross‐coupling of aryl and alkyl halides that is based on the sequence of Grignard formation and subsequent cross‐coupling. This one‐pot reaction obviates preformation of hazardous Grignard compounds and limits the amount of reactive organomagnesium intermediates to low quasi‐stationary concentrations. TMEDA=N,N,N′,N′‐tetramethylethylenediamine.
Author Mayer, Matthias
Czaplik, Waldemar Maximilian
Jacobi von Wangelin, Axel
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BackLink https://www.ncbi.nlm.nih.gov/pubmed/19067450$$D View this record in MEDLINE/PubMed
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Issue 3
Keywords Grignard reactions
HALIDES
MAGNESIUM
AMINATION
INORGANIC GRIGNARD-REAGENTS
domino reactions
cross-coupling
iron
sustainable chemistry
MECHANISMS
BETA-HYDROGENS
PROCESS SAFETY
Language English
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Notes http://dx.doi.org/10.1002/anie.200804434
This research was supported financially by Saltigo GmbH, the Deutsche Forschungsgemeinschaft (DFG, Emmy‐Noether program), the Fonds der Chemischen Industrie (FCI), and the Deutsche Bundesstiftung Umwelt (DBU). We thank Prof. H.‐G. Schmalz for generous support.
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PublicationTitle Angewandte Chemie (International ed.)
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Snippet Striking while the iron is hot: Cheap FeCl3 serves as the precatalyst for the direct cross‐coupling of aryl and alkyl halides that is based on the sequence of...
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SubjectTerms Chemistry
Chemistry, Multidisciplinary
cross‐coupling
domino reactions
Grignard reactions
iron
Physical Sciences
Science & Technology
sustainable chemistry
Title Domino Iron Catalysis: Direct Aryl-Alkyl Cross-Coupling
URI https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fanie.200804434
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