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

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 MnCl2 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 1H-NMR, which identified the key role of tris-coordinated ate-iron(II) species in the catalytic process.

SUBMITTER: Rousseau L 

PROVIDER: S-EPMC7037184 | biostudies-literature | 2020 Feb

REPOSITORIES: biostudies-literature

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

Rousseau Lidie L   Desaintjean Alexandre A   Knochel Paul P   Lefèvre Guillaume G  

Molecules (Basel, Switzerland) 20200207 3

Various substituted <i>bis</i>-(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<sub>2</sub> in THF at -5 °C within 2 h. These <i>bis</i>-(aryl)manganese reagents undergo smooth iron-catalyzed cross-couplings using 10 mol% Fe(acac)<sub>3</sub> with various functionalized alkenyl iodides and bromides in 1 h at 25 °C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly inv  ...[more]

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