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

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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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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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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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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

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The method to achieve α-brominated carboxylic acids using a mixture of phosphorus tribromide and bromine is known as the Hell–Volhard–Zelinski reaction. The reaction is catalyzed by phosphorus tribromide, which can be used directly or produced in situ from red phosphorus and bromine. The mechanism comprises PBr3 catalyzed conversion of acid to acid bromide and hydrogen bromide. The acid bromide enolizes to its enol form in the presence of HBr. The nucleophilic enol attacks the...
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Updated: Jun 12, 2025

Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
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Un catalizador adaptativo de un solo átomo de paladio que permite la conmutación de reactividad entre la borilación y

Vitthal B Saptal1, Clara Saetta2, Adriana Laufenböck3

  • 1Department of Chemistry, Materials, and Chemical Engineering "Giulio Natta", Politecnico di Milano, Piazza Leonardo da Vinci 32, 20133 Milano, Italy.

Journal of the American Chemical Society
|May 23, 2025
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Resumen
Este resumen es generado por máquina.

Desarrollamos un nuevo catalizador de un solo átomo (SAC) utilizando un método de polimerización simple. Este catalizador controla con precisión las reacciones químicas, lo que permite una síntesis eficiente y sostenible a través de procesos de autocascada.

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Área de la Ciencia:

  • Catálisis
  • Ciencias de los materiales
  • Química sintética

Sus antecedentes:

  • El desarrollo de catalizadores de un solo átomo (SAC) con funcionalidades controlables es crucial pero desafiante.
  • Los métodos existentes a menudo carecen de un control preciso de las vías catalíticas.

Objetivo del estudio:

  • Informar de un nuevo SAC con cavidades de coordinación anisotrópicas para el anclaje de átomos aislados de paladio (Pd).
  • Demostrar la capacidad del catalizador para cambiar entre distintos resultados catalíticos y permitir procesos de autocascada.

Principales métodos:

  • Polimerización en un solo paso de 2,6-diaminopiridina y cloruro cianúrico para crear cavidades anisotrópicas.
  • Anclaje de átomos aislados de Pd dentro de las cavidades.
  • Estudios mecanicistas para aclarar el papel de los átomos de Pd en las etapas catalíticas.

Principales resultados:

  • El SAC sintetizado exhibió una estabilidad excepcional y una reactividad ajustable.
  • El catalizador controlaba con éxito las vías de reacción, permitiendo un cambio entre la borilación y el acoplamiento de Suzuki.
  • Demostró un proceso de auto-cascada para transformaciones complejas con un mínimo de desperdicio.

Conclusiones:

  • El nuevo SAC con cavidades anisotrópicas ofrece un control preciso sobre las vías catalíticas.
  • Este catalizador permite transformaciones sostenibles y complejas en varios pasos a través de procesos de autocascada.
  • Destaca el potencial de la ingeniería de catálisis para revolucionar la química sintética.