Manganese‐Catalyzed Cross‐Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism

Antonacci, Giuseppe; Ahlburg, Andreas; Fristrup, Peter; Norrby, Per‐Ola; Madsen, Robert

doi:10.1002/ejoc.201700981

Cited by 17 publications

(13 citation statements)

References 50 publications

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“…Extending the scope of activated aryl halide substrates in MnCl2-catalyzed crosscoupling reactions [8].…”

Section: Methodsmentioning

confidence: 99%

Section: Arylhalides With Grignard Reagentsmentioning

confidence: 99%

“…Nearly twenty years after the initial report by Cahiez, two contributions by Madsen in 2017 provided some synthetic extensions and new mechanistic insights into the field of MnCl2catalyzed Kumada cross-coupling reactions [8,9]. The coupling of para-halo benzonitrile reagents with the cyclohexyl Grignard complex was first investigated (Scheme 4) [8]. In this case, the chloride compound provided the highest yield with 94%, whereas with the bromide analogue only a moderate 45% yield was obtained and no reaction was observed with iodide or fluoride substrates.…”

Section: Arylhalides With Grignard Reagentsmentioning

confidence: 99%

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Manganese‐Catalyzed Cross‐Coupling Processes

Jaroschik

Taillefer

2021

Manganese Catalysis in Organic Synthesis

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This chapter describes recent developments in the manganese-catalyzed crosscoupling reactions for the formation of C-C or C-heteroatom bonds, including C-N, C-O, C-S and C-B bonds. The nature of the organic halide and the organometallic coupling partner (organolithium, Grignard or organostannyl reagents) are important parameters in these reactions. Mechanistic studies are discussed as well as the recently arisen question about the influence of trace-metal contamination in certain reactions.

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“…Extending the scope of activated aryl halide substrates in MnCl2-catalyzed crosscoupling reactions [8].…”

Section: Methodsmentioning

confidence: 99%

Section: Arylhalides With Grignard Reagentsmentioning

confidence: 99%

Section: Arylhalides With Grignard Reagentsmentioning

confidence: 99%

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Manganese‐Catalyzed Cross‐Coupling Processes

Jaroschik

Taillefer

2021

Manganese Catalysis in Organic Synthesis

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“…162 In 2017, Madsen and co-workers reported the MnCl 2catalyzed cross-coupling reaction of Grignard reagents with aryl halides. 163 The reaction is limited to aryl chlorides containing a cyano or an ester group in the para position or a cyano group in the ortho position.…”

Section: Review Synthesismentioning

confidence: 99%

Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Juhász¹,

Magyar²,

Hell³

2020

Synthesis

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Transition-metal-catalyzed cross-coupling of organohalides, ethers, sulfides, amines, and alcohols (and derivatives thereof) with Grignard reagents, known as the Kumada–Tamao–Corriu reaction, can be used to prepare important intermediates in the synthesis of numerous biologically active compounds. The most frequently used transition metals are nickel, palladium, and iron, but there are several examples for cross-coupling reactions catalyzed by copper, cobalt, manganese, chromium, etc. salts and complexes. The aim of this review is to summarize the most important transition-metal-catalyzed cross-coupling reactions realized in the period 2000 to 2020.1 Introduction2 Nickel Catalysis3 Palladium Catalysis4 Iron Catalysis5 Catalysis by Other Transition Metals5.1 Cobalt Catalysis5.2 Copper Catalysis5.3 Manganese Catalysis5.4 Chromium Catalysis6 Conclusion

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“…Madsen and co-workers 63 also reported MnCl 2 -catalyzed cross coupling of Grignard reagents and various aryl halides under mild reaction conditions for 1 h (Scheme 61). In this protocol, the reaction proceeded rapidly with good resulting yields when the aryl halide component was an…”

Section: Scheme 59 Plausible Mechanism For Ligand-free Nickel-catalyzmentioning

confidence: 99%

Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

Chen

Dong

2020

Synthesis

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Organometallic compounds have become increasingly important in organic synthesis because of their high chemoselectivity and excellent reactivity. Recently, a variety of organometallic reagents were found to facilitate transition-metal-catalyzed cross-coupling reactions and nucleophilic addition reactions. Here, we have summarized the latest progress in cross-coupling reactions and in nucleophilic addition reactions with functionalized organometallic reagents present to illustrate their application value. Due to the tremendous contribution made by the Knochel group towards the development of novel organometallic reagents, this review draws extensively from their work in this area in recent years.Introduction1 Transition-Metal-Catalyzed Cross Couplings Involving Organozinc Reagents2 Transition-Metal-Catalyzed Cross Couplings Involving Organomagnesium Reagents3 Transition-Metal-Free Cross Couplings Involving Zn and Mg Organometallic Reagents4 Nucleophilic Additions Involving Zn and Mg Organometallic Reagents5 Cross-Coupling Reactions or Nucleophilic Additions Involving Mn, Al-, La-, Li-, Sm- and In-Organometallics6 Conclusion

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Manganese‐Catalyzed Cross‐Coupling of Aryl Halides and Grignard Reagents by a Radical Mechanism

Cited by 17 publications

References 50 publications

Manganese‐Catalyzed Cross‐Coupling Processes

Manganese‐Catalyzed Cross‐Coupling Processes

Transition-Metal-Catalyzed Cross-Coupling Reactions of Grignard Reagents

Recent Progress in Utilization of Functionalized Organometallic Reagents in Cross Coupling Reactions and Nucleophilic Additions

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