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Videos de Conceptos Relacionados

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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.
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.
Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

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.
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

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...
Heterogeneous Catalysis01:22

Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...

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Optimización de alto rendimiento de la borilación C-H catalizada por Ir: un tutorial para aplicaciones prácticas.

Sean M Preshlock1, Behnaz Ghaffari, Peter E Maligres

  • 1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824-1322, USA.

Journal of the American Chemical Society
|March 29, 2013
PubMed
Resumen

El cribado de alto rendimiento optimizó las borilaciones C-H catalizadas por iridio probando varias condiciones. Esta investigación identificó factores clave para desafiar los sustratos, mejorando la eficiencia catalítica.

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Área de la Ciencia:

  • Química organometálica Química orgánica de los metales.
  • La catálisis de la catálisis.
  • Química orgánica sintética y orgánica.

Sus antecedentes:

  • La borilación C-H catalizada por iridio es una transformación crucial en la síntesis orgánica.
  • La optimización de las condiciones de reacción es esencial para una borilación eficiente y selectiva.
  • Las condiciones catalíticas estándar a menudo enfrentan limitaciones con ciertos sustratos.

Objetivo del estudio:

  • Evaluar sistemáticamente la eficiencia de las borilaciones C-H catalizadas por iridio.
  • Para identificar los parámetros de reacción óptimos, incluidos el precatalizador, el reactivo de boro, el ligando y el disolvente.
  • Para descubrir nuevas condiciones para sustratos desafiantes.

Principales métodos:

  • Se utilizó el cribado de alto rendimiento (HTS) para evaluar múltiples variables de reacción simultáneamente.
  • Investigó el impacto del precatalizador, el reactivo de boro, el ligando, el orden de adición, la temperatura, el disolvente y el sustrato.
  • Variación sistemática realizada de los componentes y condiciones de la reacción.

Principales resultados:

  • Prácticas establecidas validadas en la borilación de C-H catalizada por iridio.
  • Descubrió condiciones de reacción no convencionales que mejoraron significativamente el rendimiento del sustrato.
  • Se identificaron parámetros específicos críticos para la eficiencia de la borilación en diversos sustratos.

Conclusiones:

  • El estudio proporciona información valiosa sobre la optimización de las borilaciones C-H catalizadas por iridio.
  • Los hallazgos guiarán el desarrollo de nuevos sistemas catalíticos para sustratos difíciles.
  • Este trabajo avanza en el alcance y la aplicabilidad de la química de la borilación C-H.