A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, In Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines

While iron-bisphosphines have emerged as effective catalysts for C—C cross-coupling, the nature of the in situ formed iron species, elucidation of the active catalysts and the mechanisms of catalysis have remained elusive. A combination of Fe Mössbauer and magnetic circular dichroism (MCD) spectrosc...

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Publicado en:Journal of the American Chemical Society Vol. 136; no. 25; pp. 9132 - 9144
Autores principales: Daifuku, Stephanie L., Al-Afyouni, Malik H., Snyder, Benjamin E. R., Kneebone, Jared L., Neidig, Michael L.
Formato: Artículo
Publicado: American Chemical Society 6/25/2014
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Acceso en línea:Ver este registro en EBSCOhost
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      dt: 6/25/2014
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        10.1021/ja503596m
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        atl: A Combined Mössbauer, Magnetic Circular Dichroism, and Density Functional Theory Approach for Iron Cross-Coupling Catalysis: Electronic Structure, In Situ Formation, and Reactivity of Iron-Mesityl-Bisphosphines
      aug:
        au:
          Daifuku, Stephanie L.
          Al-Afyouni, Malik H.
          Snyder, Benjamin E. R.
          Kneebone, Jared L.
          Neidig, Michael L.
        affil: Department of Chemistry, University of Rochester, Rochester, New York 14627, United States
      su:
        Iron compounds
        Diphosphine
        Mössbauer spectroscopy
        Magnetic circular dichroism
        Density functional theory
        Coupling reactions (Chemistry)
        Electronic structure
        Reaction mechanisms (Chemistry)
      sug:
        subj:
          Iron compounds
          Diphosphine
          Mössbauer spectroscopy
          Magnetic circular dichroism
          Density functional theory
          Coupling reactions (Chemistry)
          Electronic structure
          Reaction mechanisms (Chemistry)
      ab: While iron-bisphosphines have emerged as effective catalysts for C—C cross-coupling, the nature of the in situ formed iron species, elucidation of the active catalysts and the mechanisms of catalysis have remained elusive. A combination of Fe Mössbauer and magnetic circular dichroism (MCD) spectroscopies of well-defined and in situ formed mesityl-iron(II)-SciOPP species combined with density functional theory (DFT) investigations provides the first direct insight into electronic structure, bonding and in situ speciation of mesityl-iron(Il)-bisphosphines in the Kumada cross-coupling of MesMgBr and primary alkyl halides using FeCl(SciOPP). Combined with freeze-trapped solution Mossbauer studies of reactions with primary alkyl halides, these studies demonstrate that distorted square-planar FeMes(SciOPP) is the active catalyst for cross-coupling and provide insight into the molecular-level mechanism of catalysis. These studies also define the effects of key reaction protocol details, including the role of the slow Grignard addition method and the addition of excess SciOPP ligand, in leading to high product yields and selectivities.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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