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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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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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Introduction
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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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Acoplamiento catalítico deshidrogenativo C-C por un complejo de iridio ligado por pinza

Miles Wilklow-Marnell1, Bo Li2, Tian Zhou2

  • 1Department of Chemistry, University of Rochester , Rochester, New York 14627, United States.

Journal of the American Chemical Society
|June 9, 2017
PubMed
Resumen

Los catalizadores de iridio y pinza facilitan el acoplamiento deshidrogenativo de los arenos vinílicos para formar diarilbutadienos. Esta reacción puede proceder por desproporcionamiento o con aceptores de hidrógeno, dando hasta un 90% de producto.

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Área de la Ciencia:

  • Química organometálica
  • Catálisis
  • Síntesis orgánica

Sus antecedentes:

  • Las arenas de vinilo son bloques de construcción versátiles en la síntesis orgánica.
  • Los métodos catalíticos eficientes para la funcionalización de C-H son muy buscados.

Objetivo del estudio:

  • Investigar la actividad catalítica de los complejos pinza-iridio en el acoplamiento deshidrogenativo de las arenas vinilo.
  • Para aclarar el mecanismo de reacción y explorar el alcance del sustrato.

Principales métodos:

  • Catálisis con fragmentos de iridio de pinza (iPrPCP) Ir.
  • Cálculos de la Teoría Funcional de la Densidad (DFT).
  • Síntesis y caracterización de los productos intermedios del metalloindeno.
  • Reacciones con estirenos sustituidos.

Principales resultados:

  • Formación predominante de (E,E) -1,4-diarilo-1,3-butadienos mediante el acoplamiento deshidrogenativo.
  • El rendimiento de hasta el 90% se consigue mediante desproporcionamiento o con aceptores de hidrógeno de sacrificio.
  • El mecanismo implica la adición de doble C-H para formar un intermediario de iridio (III) metaloindeno.
  • Se ha demostrado el acoplamiento de enlaces C(sp2)-H y C(sp3)-H utilizando 2,4,6-trimetilestireno.

Conclusiones:

  • Los complejos de pinza e iridio son catalizadores eficaces para el acoplamiento deshidrogenativo del vinil areno.
  • La reacción se lleva a cabo a través de un intermediario de metalloindeno.
  • El sistema catalítico es versátil y puede acoplar varios enlaces C-H.