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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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C-F sp(2) bond functionalization mediated by niobium complexes.

Michael Nechayev1, Thomas L Gianetti, Robert G Bergman

  • 1Department of Chemistry, University of California, Berkeley, California 94720, USA. arnold@berkeley.edu.

Dalton Transactions (Cambridge, England : 2003)
|July 29, 2015
PubMed
Summary

This study demonstrates the functionalization of carbon-fluorine bonds using isocyanide insertion into a niobium complex. Subsequent reactions with phenylsilane reveal divergent reactivity pathways for the resulting compounds.

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Area of Science:

  • Organometallic Chemistry
  • Niobium Catalysis
  • Fluorine Chemistry

Background:

  • Carbon-fluorine (C-F) bonds are prevalent but challenging to functionalize.
  • Organometallic complexes offer unique reactivity for C-F bond activation.

Purpose of the Study:

  • To explore the insertion chemistry of isocyanides into C-F bonds using a niobium complex.
  • To investigate the subsequent reactivity of the functionalized complexes.

Main Methods:

  • Oxidative addition of C-F bonds to a β-diketiminate niobium(III) imido complex.
  • Characterization of resulting complexes using NMR spectroscopy and X-ray diffraction.
  • Treatment with phenylsilane to induce H/F exchange and hydride transfer.

Main Results:

  • Successful insertion of isocyanide molecules into C-F bonds was achieved.
  • Characterization confirmed the structure of the novel niobium complexes.
  • Phenylsilane treatment led to H/F exchange and hydride transfer, with divergent reactivity observed between aryl and tert-butyl isocyanide products.

Conclusions:

  • Isocyanide insertion provides a viable route for functionalizing C-F bonds in niobium complexes.
  • The study highlights the potential for controlled C-F bond transformations.
  • Divergent reactivity pathways offer opportunities for developing new synthetic methodologies.