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Accessing Valuable Ligand Supports for Transition Metals: A Modified, Intermediate Scale Preparation of 1,2,3,4,5-Pentamethylcyclopentadiene
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Nucleophilic scandium carbene complexes.

Marie Fustier1, Xavier F Le Goff, Pascal Le Floch

  • 1Laboratoire Hétéroéléments et Coordination, UMR CNRS 7653 (DCPH), Département de Chimie, Ecole Polytechnique, 91128 Palaiseau Cedex, France.

Journal of the American Chemical Society
|September 4, 2010
PubMed
Summary

Researchers synthesized a novel scandium carbene complex using a geminal dianion precursor. This complex exhibits nucleophilic carbene behavior and facilitates a unique scandia-Wittig reaction, forming alkene derivatives and a rare oxo-scandium species.

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Isolating Free Carbenes, their Mixed Dimers and Organic Radicals

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Area of Science:

  • Organometallic Chemistry
  • Scandium Complexes
  • Carbene Chemistry

Background:

  • Scandium complexes are valuable in catalysis.
  • Nucleophilic carbene complexes offer unique reactivity.
  • Synthesis of novel organoscandium compounds is an active research area.

Purpose of the Study:

  • To synthesize and characterize a novel nucleophilic scandium carbene complex.
  • To investigate the electronic structure and bonding in the scandium carbene complex.
  • To explore the reactivity of the scandium carbene complex in organic transformations.

Main Methods:

  • Salt metathesis reaction using ScCl(3)(THF)(3) and a geminal dianion precursor.
  • X-ray crystallography for structural determination.
  • Natural Bond Orbital (NBO) analysis for electronic structure investigation.

Main Results:

  • Successful synthesis of a nucleophilic scandium carbene complex (2) in 52% yield.
  • X-ray structure and NBO analysis confirmed a significant Sc-C double interaction.
  • The complex demonstrated nucleophilic carbene behavior, reacting with benzophenone.
  • A scandia-Wittig reaction occurred, yielding an alkene and a rare μ(3)-oxo-Sc species.

Conclusions:

  • A novel nucleophilic scandium carbene complex has been synthesized and characterized.
  • The electronic structure supports significant Sc-C bonding with nucleophilic carbene character.
  • The complex is reactive in a scandia-Wittig reaction, showcasing its synthetic utility.