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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Two NMR-active nuclei bonded to a central atom can be involved in geminal or two-bond coupling. Geminal coupling is commonly seen between diastereotopic protons in chiral molecules and unsymmetrical alkenes, among others.
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Vicinal or three-bond coupling is commonly observed between protons attached to adjacent carbons. Here, nuclear spin information is primarily transferred via electron spin interactions between adjacent C‑H bond orbitals. This generally favors the antiparallel arrangement of spins, so 3J values are usually positive.
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CS2 Reductive Coupling to Acetylenedithiolate by a Dinuclear Ytterbium(II) Complex.

Davide Toniolo1, Aurélien R Willauer1, Julie Andrez1

  • 1Institut des Sciences et Ingénierie Chimiques, Ecole Polytechnique Fédérale de Lausanne (EPFL), 1015, Lausanne, Switzerland.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 9, 2019
PubMed
Summary

Researchers discovered new ways to activate carbon disulfide (CS2) using a dinuclear ytterbium(II) complex. This work presents the first acetylenedithiolate ligand formed from CS2 reduction, opening new avenues for C-C bond formation.

Keywords:
carbon disulfide reductionlanthanidespolynuclear complexessmall-molecule activationytterbium

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Area of Science:

  • Organometallic Chemistry
  • Inorganic Chemistry
  • Materials Science

Background:

  • Carbon disulfide (CS2) activation is crucial for synthesizing novel compounds and forming carbon-carbon bonds.
  • Dinuclear metal complexes offer unique reactivity profiles compared to their mononuclear counterparts.
  • Understanding the reduction pathways of small molecules like CS2 is key to developing new synthetic methodologies.

Purpose of the Study:

  • To investigate the reactivity of a dinuclear ytterbium(II) complex with carbon disulfide.
  • To characterize the reduction products of carbon disulfide mediated by the ytterbium complex.
  • To elucidate the mechanism of CS2 reduction and the formation of novel ligands.

Main Methods:

  • Synthesis and isolation of a dinuclear ytterbium(II) complex [Yb2 L4], where L = (OtBu)3SiO-.
  • Reaction of the ytterbium complex with carbon disulfide (CS2).
  • Crystallographic characterization of the resulting reduction products, including [Yb2 L4 (μ-C2 S2)].
  • Computational studies to analyze the binding modes and reaction mechanisms.

Main Results:

  • Isolation of unprecedented reduction products from the reaction of [Yb2 L4] with CS2.
  • Crystallographic determination of complex [Yb2 L4 (μ-C2 S2)], featuring the first example of an acetylenedithiolate ligand derived from CS2 metal reduction.
  • Computational analysis revealed an unusual binding mode of CS22- in a key intermediate [Yb2 L4 (μ-CS2)], attributed to the dinuclear nature of the ytterbium complex.

Conclusions:

  • The dinuclear ytterbium(II) complex facilitates the reduction of carbon disulfide to form an acetylenedithiolate ligand.
  • This reactivity highlights the potential of dinuclear complexes in small molecule activation and C-C bond formation.
  • The findings provide fundamental insights into the coordination and reduction chemistry of CS2 with early transition metals.