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

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

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 &#8722;5 &#176;C within 2 h. These <i>bis</...

Full description

Bibliographic Details
Main Authors: Lidie Rousseau, Alexandre Desaintjean, Paul Knochel, Guillaume Lefèvre
Format: Article
Language:English
Published: MDPI AG 2020-02-01
Series:Molecules
Subjects:
iron catalysis
cross-coupling
<i>bis</i>-(aryl)manganese
alkenyl halides
<i>ate</i> iron(ii) complex
Online Access:https://www.mdpi.com/1420-3049/25/3/723
id doaj-76d544aa42324dd6b679b4f45d2cb000
record_format Article
spelling doaj-76d544aa42324dd6b679b4f45d2cb0002020-11-25T00:19:32ZengMDPI AGMolecules1420-30492020-02-0125372310.3390/molecules25030723molecules25030723Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic InvestigationsLidie Rousseau0Alexandre Desaintjean1Paul Knochel2Guillaume Lefèvre3Chimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences (i-CLeHS FRE2027), CSB2D, 75005 Paris, FranceDepartment of Chemistry, Ludwig-Maximilians-Universitat München, Butenandstr. 5-13, Haus F, 81377 Munich, GermanyDepartment of Chemistry, Ludwig-Maximilians-Universitat München, Butenandstr. 5-13, Haus F, 81377 Munich, GermanyChimie ParisTech, PSL University, CNRS, Institute of Chemistry for Life and Health Sciences (i-CLeHS FRE2027), CSB2D, 75005 Paris, FranceVarious 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 &#8722;5 &#176;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 &#176;C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic <sup>1</sup>H-NMR, which identified the key role of <i>tris</i>-coordinated <i>ate</i>-iron(II) species in the catalytic process.https://www.mdpi.com/1420-3049/25/3/723iron catalysiscross-coupling<i>bis</i>-(aryl)manganesealkenyl halides<i>ate</i> iron(ii) complex
collection DOAJ
language English
format Article
sources DOAJ
author Lidie Rousseau
Alexandre Desaintjean
Paul Knochel
Guillaume Lefèvre
spellingShingle Lidie Rousseau
Alexandre Desaintjean
Paul Knochel
Guillaume Lefèvre
Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
Molecules
iron catalysis
cross-coupling
<i>bis</i>-(aryl)manganese
alkenyl halides
<i>ate</i> iron(ii) complex
author_facet Lidie Rousseau
Alexandre Desaintjean
Paul Knochel
Guillaume Lefèvre
author_sort Lidie Rousseau
title Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
title_short Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
title_full Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
title_fullStr Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
title_full_unstemmed Iron-Catalyzed Cross-Coupling of <i>Bis</i>-(aryl)manganese Nucleophiles with Alkenyl Halides: Optimization and Mechanistic Investigations
title_sort iron-catalyzed cross-coupling of <i>bis</i>-(aryl)manganese nucleophiles with alkenyl halides: optimization and mechanistic investigations
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-02-01
description 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 &#8722;5 &#176;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 &#176;C. The aryl-alkenyl cross-coupling reaction mechanism was thoroughly investigated through paramagnetic <sup>1</sup>H-NMR, which identified the key role of <i>tris</i>-coordinated <i>ate</i>-iron(II) species in the catalytic process.
topic iron catalysis
cross-coupling
<i>bis</i>-(aryl)manganese
alkenyl halides
<i>ate</i> iron(ii) complex
url https://www.mdpi.com/1420-3049/25/3/723
work_keys_str_mv AT lidierousseau ironcatalyzedcrosscouplingofibisiarylmanganesenucleophileswithalkenylhalidesoptimizationandmechanisticinvestigations
AT alexandredesaintjean ironcatalyzedcrosscouplingofibisiarylmanganesenucleophileswithalkenylhalidesoptimizationandmechanisticinvestigations
AT paulknochel ironcatalyzedcrosscouplingofibisiarylmanganesenucleophileswithalkenylhalidesoptimizationandmechanisticinvestigations
AT guillaumelefevre ironcatalyzedcrosscouplingofibisiarylmanganesenucleophileswithalkenylhalidesoptimizationandmechanisticinvestigations
_version_ 1725371604221820928

Similar Items