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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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Hydroboration-Oxidation of Alkenes03:08

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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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

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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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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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Reduction of Alkenes: Catalytic Hydrogenation02:13

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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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Nanocúmulos de metal de precisión atómica como transferidores de electrones individuales para la hidroborilación

Wanli Zhu1,2, Sheng Zhang1,2, Weigang Fan1,2

  • 1Institute of Physical Science and Information Technology, Anhui University, Hefei, Anhui 230601, P. R. China.

Precision chemistry
|August 29, 2025
PubMed
Resumen

Este estudio introduce un nuevo modo de catálisis de transferencia de electrones (SET) para nanoagrupaciones metálicas, mejorando la actividad catalítica y la estabilidad. Este enfoque supera la inhibición del ligando, lo que permite una hidroborilación eficiente de alquinas en condiciones suaves.

Palabras clave:
nanoagrupación de metales de precisión atómicaRadical de borilohidroborilacióntransferencia de un solo electróncatálisis en tándem

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Área de la Ciencia:

  • Ciencia en nanoescala
  • Catálisis
  • Química de los materiales

Sus antecedentes:

  • Los nanocúmulos metálicos ofrecen estructuras precisas para el estudio de la catálisis a nanoescala.
  • Los ligandos en los catalizadores de nanocluster a menudo inhiben la actividad desactivando las superficies.
  • Un equilibrio entre la actividad catalítica y la estabilidad es crucial para los catalizadores de nanoagrupación.

Objetivo del estudio:

  • Introducir un nuevo modo catalítico para los nanocúmulos metálicos.
  • Para abordar el desafío de la inhibición del ligando en la catálisis de nanoclusters.
  • Proporcionar una solución para la compensación entre la actividad y la estabilidad en los catalizadores de nanoagrupación metálica.

Principales métodos:

  • Iniciación de la catálisis a través de la transferencia de un solo electrón (SET) sin degradación de nanoagrupaciones.
  • Aplicación del nuevo modo en reacciones de hidroborilación de alquinos.
  • Demostrar el reciclado y la aplicación de catalizadores en procesos en tándem.

Principales resultados:

  • El nuevo modo de activación SET permite la catálisis sin destruir la integridad del nanocluster.
  • Se logra una baja carga del catalizador (0,01 mol%), una alta frecuencia de rotación (TOF) y condiciones de reacción suaves.
  • Se aplicó con éxito el catalizador [Au1Cu14 ((TBBT) 12 ((PPh3) 6) + en la hidroborilación de alquinos, mejorando la selectividad y la tolerancia del grupo funcional.
  • Se han demostrado reacciones en tándem eficientes, incluida la hidroborilación-deuteración y la hidroborilación-isomerización.

Conclusiones:

  • El modo catalítico de transferencia de electrones individuales (SET) desarrollado ofrece una solución viable para la inhibición del ligando en la catálisis de nanoagrupaciones metálicas.
  • Este enfoque mejora tanto la actividad como la estabilidad de los catalizadores de nanoagrupación.
  • La utilidad demostrada en la hidroborilación de alquinos y las reacciones en tándem pone de relieve la amplia aplicabilidad de esta nueva estrategia catalítica.