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Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Free-Radical Chain Reaction and Polymerization of Alkenes02:35

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The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.
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Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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The anti-Markovnikov addition of hydrogen halides to an alkene is thermodynamically feasible only with HBr. The radical addition reaction with other hydrogen halides like HCl and HI is thermodynamically unfavorable.
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Difuncionalización catalítica de un alqueno a través de los radicales imidados

Kohki M Nakafuku1, Stacy C Fosu1, David A Nagib1

  • 1Department of Chemistry and Biochemistry , The Ohio State University , Columbus , Ohio 43210 , United States.

Journal of the American Chemical Society
|August 30, 2018
PubMed
Resumen

Los investigadores desarrollaron un nuevo método catalítico utilizando radicales imidados para la difuncionalización de alceno. Este enfoque fotocatalítico permite la hidroaminación, la aminoalquilación y la aminoarilación de los alcoholes aliloides con una amplia utilidad.

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Área de la Ciencia:

  • Química orgánica
  • Fotocatálisis
  • La Química Radical

Sus antecedentes:

  • Los radicales imidados son intermediarios versátiles en la síntesis orgánica.
  • El desarrollo de métodos catalíticos para generar y utilizar radicales centrados en N es crucial para las nuevas vías de reacción.

Objetivo del estudio:

  • Establecer la primera estrategia catalítica para el aprovechamiento de los radicales imidados.
  • Para permitir la difuncionalización de alceno de los alcoholes aliloicos a través de la reducción fotocatalítica de los imidatos oxímicos.

Principales métodos:

  • Reducción fotocatalítica de los imidatos oxímicos para generar radicales imidados.
  • Exploración de las reacciones radicales intra e intermoleculares consecutivas.
  • Investigación de tres mecanismos radicales distintos: la hidroaminación, la aminoalquilación y la aminoarilación.

Principales resultados:

  • Desarrollo exitoso de una estrategia catalítica para la generación y reactividad de radicales imidados.
  • Demostración de la difuncionalización de alceno de los alcoholes aliloides.
  • Se obtienen productos de hidroaminación, aminoalquilación y aminoarilación a través de vías radicales distintas.

Conclusiones:

  • Este trabajo presenta un método catalítico novedoso y ampliamente aplicable para la química de los radicales imidados.
  • El enfoque desarrollado amplía el conjunto de herramientas para las reacciones radicales centradas en N y ofrece vías complementarias a los métodos existentes.