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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen double...
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Extraction: Advanced Methods

Metal ions can be separated from one another by complexation with organic ligands–the chelating agent– to form uncharged chelates. Here, the chelating agent must contain hydrophobic groups and behave as a weak acid, losing a proton to bind with the metal. Since most organic ligands used in this process are insoluble or undergo oxidation in the aqueous phase, the chelating agent is initially added to the organic phase and extracted into the aqueous phase. The metal-ligand complex is formed in...
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Metal-Ligand Bonds

The hemoglobin in the blood, the chlorophyll in green plants, vitamin B-12, and the catalyst used in the manufacture of polyethylene all contain coordination compounds. Ions of the metals, especially the transition metals, are likely to form complexes.
In these complexes, transition metals form coordinate covalent bonds, a kind of Lewis acid-base interaction in which both of the electrons in the bond are contributed by a donor (Lewis base) to an electron acceptor (Lewis acid). The Lewis acid in...
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Colors and Magnetism

Color in Coordination Complexes
When atoms or molecules absorb light at the proper frequency, their electrons are excited to higher-energy orbitals. For many main group atoms and molecules, the absorbed photons are in the ultraviolet range of the electromagnetic spectrum, which cannot be detected by the human eye. For coordination compounds, the energy difference between the d orbitals often allows photons in the visible range to be absorbed and emitted, which is seen as colors by the human eye.

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Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
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Published on: July 28, 2018

Agentes trifluorometiladores activos de complejos bien definidos de cobre ((I) -CF3).

Galyna G Dubinina1, Hideki Furutachi, David A Vicic

  • 1Department of Chemistry, University of Hawaii, 2545 McCarthy Mall, Honolulu, Hawaii 96822, USA.

Journal of the American Chemical Society
|June 12, 2008
PubMed
Resumen

Los investigadores informan de los primeros complejos aislables de cobre (I) trifluorometil (CF3). Estos nuevos complejos de cobre N-heterocíclicos apoyados en carbenos transfieren de manera eficiente grupos CF3 a haluros orgánicos.

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Área de la Ciencia:

  • Química organometálica Química orgánica de los metales.
  • Química del flúor Química del flúor
  • La catálisis de la catálisis.

Sus antecedentes:

  • Los complejos de cobre son catalizadores versátiles.
  • Los grupos trifluorometilo (CF3) son importantes en productos farmacéuticos y materiales.
  • Los complejos Cu(I) -CF3 aislables son difíciles de sintetizar.

Objetivo del estudio:

  • Sintetizar y caracterizar nuevos complejos aislables de cobre (I) trifluorometil (CF3).
  • Para investigar las características estructurales de estos complejos.
  • Para evaluar su utilidad en las reacciones de trifluorometilación.

Principales métodos:

  • Reacción de los complejos de tert-butóxido de cobre apoyados por carbenos N-heterocíclicos (NHC) con Me3Si-CF3.3.
  • Caracterización estructural mediante cristalografía de rayos X.
  • Generación in situ de complejos trifluorometilo de cobre para reacciones de transferencia.

Principales resultados:

  • Se informan los primeros ejemplos de complejos Cu(I) -CF3 aislables y estructuralmente caracterizados.
  • Las estructuras complejas dependen de la saturación del anillo NHC.
  • El in situ generado (SIiPr) Cu-CF3 transfirió eficientemente el grupo CF3 a haluros orgánicos en condiciones suaves.

Conclusiones:

  • Se han sintetizado y caracterizado nuevos complejos Cu(I) -CF3 soportados por NHC.
  • Estos complejos ofrecen una nueva plataforma para la química de la trifluorometilación.
  • La metodología desarrollada proporciona una ruta suave y eficiente para la introducción de grupos CF3 en moléculas orgánicas.