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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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Regioselectivity and Stereochemistry of Hydroboration02:36

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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...
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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Preparation of Alcohols via Addition Reactions02:15

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Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
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Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

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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...
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Hidrogenación asimétrica notablemente fácil promovida por el boro y catalizada por el rodio de alquenos tri y

Veronika M Shoba1, James M Takacs1

  • 1Department of Chemistry, University of Nebraska-Lincoln , Lincoln, Nebraska 68588-0304, United States.

Journal of the American Chemical Society
|April 11, 2017
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio demuestra un nuevo método de hidrogenación asimétrica catalítica (CAH) para alquenos desafiantes. El proceso utiliza un promotor de borano en condiciones suaves, logrando una alta enantioselectividad para sustratos tri y tetrasubstituidos.

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Área de la Ciencia:

  • Química orgánica
  • Catálisis asimétrica
  • Reacciones de hidrogenación

Sus antecedentes:

  • Las reacciones dirigidas por oximas ofrecen vías sintéticas únicas.
  • La hidrogenación asimétrica catalítica (CAH) es crucial para la síntesis de moléculas quirales.
  • El desarrollo de CAH eficientes para alquenos estéricamente obstaculizados sigue siendo un desafío.

Objetivo del estudio:

  • Desarrollar un nuevo método de hidrogenación asimétrica catalítica (CAH).
  • Para permitir la CAH de alquenos tri y tetrasubstituidos desafiantes.
  • Para lograr una alta enantioselectividad en condiciones de reacción suaves.

Principales métodos:

  • Las reacciones dirigidas por oximos fueron modificadas mediante la introducción de una fuente de protones o una atmósfera de hidrógeno.
  • El pinacolborano fue empleado como promotor de borano para la CAH.
  • Las reacciones se llevaron a cabo en condiciones suaves (temperatura ambiente, tiempos moderados).

Principales resultados:

  • La hidroboración dirigida por oxima fue desviada con éxito a CAH.
  • Los alquenos tri y tetrasubstituidos, incluidos todos los tipos alquilo, se hidrogenaron con altas proporciones de enantiómeros (hasta 99:1).
  • El método solo requiere un ligero exceso de H2.

Conclusiones:

  • Se ha establecido un nuevo y eficiente protocolo de CAH.
  • Este método amplía el alcance de los sustratos susceptibles a la hidrogenación asimétrica.
  • Las condiciones suaves y la alta selectividad ofrecen ventajas sobre los sistemas catalíticos existentes.