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Videos de Conceptos Relacionados

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
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Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
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Activación de un catalizador de oro de hidroaminación mediante la oxidación de un ligando de clorostibina Z redox no

Haifeng Yang1, François P Gabbaï1

  • 1Department of Chemistry, Texas A&M University , College Station, Texas 77843-3255, United States.

Journal of the American Chemical Society
|October 13, 2015
PubMed
Resumen

Los investigadores exploraron complejos de oro con ligandos de clorostibina para la catálisis controlada por redox. La oxidación de estos complejos mejoró las interacciones oro-antimonio, lo que condujo a los centros de oro ácido de Lewis que activan las alquinas para las reacciones de hidroaminación.

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Área de la Ciencia:

  • Química organometálica
  • Catálisis
  • Diseño del ligando

Sus antecedentes:

  • La investigación de nuevas plataformas para la catálisis controlada por redox es crucial.
  • Los ligandos no inocentes ofrecen una reactividad única al participar en procesos redox.

Objetivo del estudio:

  • Para explorar el comportamiento redox de los ligandos de clorostibina coordinados con el oro.
  • Desarrollar nuevos complejos de oro para aplicaciones catalíticas.

Principales métodos:

  • Síntesis y caracterización de los complejos de clorostibina de oro.
  • Reacciones de oxidación con fuentes de PhICl2 y fluoruro.
  • Estudios experimentales y computacionales de las interacciones electrónicas.
  • Abstracción de cloruro para formar especies de oro catiónico.
  • Pruebas catalíticas para la hidroaminación de alquinos.

Principales resultados:

  • Los complejos de clorostibina de oro fueron sintetizados y oxidados a triclorostiborano y análogos de trifluoruro.
  • La oxidación fortaleció significativamente la interacción donante-receptor de Au→Sb.
  • Se generaron especies de oro catiónico, con [3](+) que exhiben una acidez de Lewis mejorada.
  • El centro de oro ácido de Lewis en [3] ((+) activó las alquinas terminales para la hidroaminación.

Conclusiones:

  • El estado redox de los ligandos no inocentes puede ajustar efectivamente la actividad catalítica de los centros metálicos.
  • Este estudio presenta una nueva estrategia para el diseño de catalizadores de oro con conmutación redox.