C-H Bond Activation of Benzene by Unsaturated η-Cyclopropene and η-Benzyne Complexes of Niobium.

We report the synthesis of a niobium cyclopropyl complex, TpNbMe(c-CH)(MeCCMe), and show that thermal loss of methane from this compound generates an intermediate that is capable of activating both aliphatic and aromatic C-H bonds. Isotopic labeling, trapping studies, a detailed kinetic analysis, an...

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Published in:Journal of the American Chemical Society Vol. 132; no. 40; pp. 14239 - 14251
Main Authors: Boulho, Cédric, Oulié, Pascal, Vendier, Laure, Etienne, Michel, Pimienta, Véronique, Locati, Abel, Bessac, Fabienne, Maseras, Feliu, Pantazis, Dimitrios A., McGrady, John E.
Format: Article
Published: American Chemical Society 10/13/2010
Subjects:
Online Access:View this record in EBSCOhost
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      dt: 10/13/2010
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        atl: C-H Bond Activation of Benzene by Unsaturated η-Cyclopropene and η-Benzyne Complexes of Niobium.
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          Boulho, Cédric
          Oulié, Pascal
          Vendier, Laure
          Etienne, Michel
          Pimienta, Véronique
          Locati, Abel
          Bessac, Fabienne
          Maseras, Feliu
          Pantazis, Dimitrios A.
          McGrady, John E.
        affil:
          CNRS, Laboratoire de Chimie de Coordination (LCC), 205 Route de Narbonne, F-31077 Toulouse, France
          Université de Toulouse, UPS, INPT, LCC, F-31077 Toulouse
          France, Université de Toulouse, UPS, IMRCP, 118 Route de Narbonne, F-31062 Toulouse, France
          Institute of Chemical Research of Catalonia (1CIQ), Avgda. Palsos Catalans 16, 43007 Tarragona, Spain
          Unitat de Quimica Fisica, Edition, Universitat Autonoma de Barcelona, 08193 Bellaterra, Catalonia, Spain
          Department of Chemistry, Inorganic Chemistry Laboratory, University of Oxford South Parks Road, Oxford OXI 3QR, United Kingdom
      su:
        Complex compounds synthesis
        Niobium
        Benzene
        Density functionals
        Hydrogen spectra
        Reactivity (Chemistry)
      sug:
        subj:
          Complex compounds synthesis
          Niobium
          Benzene
          Density functionals
          Hydrogen spectra
          Reactivity (Chemistry)
      ab: We report the synthesis of a niobium cyclopropyl complex, TpNbMe(c-CH)(MeCCMe), and show that thermal loss of methane from this compound generates an intermediate that is capable of activating both aliphatic and aromatic C-H bonds. Isotopic labeling, trapping studies, a detailed kinetic analysis, and density functional theory all suggest that the active intermediate is an η-cyclopropene complex formed via β-hydrogen abstraction rather than an isomeric cyclopropylidene species. C-H activation chemistry of this type represents a rather unusual reactivity pattern for η-alkene complexes but is favored in this case by the strain in the C ring which prevents the decomposition of the key intermediate via loss of cyclopropene.
      pubtype: Academic Journal
      doctype: Article
      src: R
    language: English
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          year: 2010
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