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Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations

Lidie Rousseau 1, 2 Alexandre Desaintjean 3 Paul Knochel 3 Guillaume Lefèvre 2, * 
* Corresponding author
1 LCMCE - Laboratoire de Chimie Moléculaire et de Catalyse pour l'Energie (ex LCCEF)
NIMBE UMR 3685 - Nanosciences et Innovation pour les Matériaux, la Biomédecine et l'Energie (ex SIS2M)
Abstract : Various substituted $bis$-(aryl)manganese species were prepared from aryl bromides by one-pot insertion of magnesium turnings in the presence of LiCl and in situ trans-metalation with MnCl$_2$ in THF at −5°C within 2 h. These $bis$-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)$_3$ with various functionalized alkenyl iodides and bromides in 1 h at 25°C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic $^1$H-NMR, which identified the key role of $tris$-coordinated $ate$-iron(II) species in the catalytic process.
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Submitted on : Wednesday, February 12, 2020 - 3:05:44 PM
Last modification on : Sunday, June 26, 2022 - 2:46:51 AM
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Lidie Rousseau, Alexandre Desaintjean, Paul Knochel, Guillaume Lefèvre. Iron-Catalyzed Cross-Coupling of Bis-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations. Molecules, 2020, 25 (3), pp.723. ⟨10.3390/molecules25030723⟩. ⟨cea-02476144⟩

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