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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

Regioselectivity and Stereochemistry of Hydroboration

7.8K
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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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.8K
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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Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids01:02

Loss of Carboxy Group as CO2: Decarboxylation of β-Ketoacids

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Carboxylic acids, upon heating, undergo a decarboxylation reaction by releasing carbon dioxide gas. Monocarboxylic acids do not undergo decarboxylation easily. However, a silver salt of carboxylic acid reacts with bromine or iodine under high temperature to release carbon dioxide gas and forms halide with one less carbon. This reaction is called the Hunsdiecker reaction.
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α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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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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Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives01:35

Loss of Carboxy Group as CO2: Decarboxylation of Malonic Acid Derivatives

1.8K
Just like β-keto acids—which upon thermal decarboxylation form ketones—β-dicarboxylic acids undergo decarboxylation to generate monocarboxylic acids with the liberation of carbon dioxide.
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Updated: May 5, 2026

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.1K

Descarboxilación por borilación

Chao Li1, Jie Wang1, Lisa M Barton1

  • 1Department of Chemistry, The Scripps Research Institute (TSRI), La Jolla, CA 92037, USA.

Science (New York, N.Y.)
|April 15, 2017
PubMed
Resumen
Este resumen es generado por máquina.

Una nueva reacción catalizada por níquel convierte eficientemente los ácidos carboxílicos en ésteres de boronato. Este método simplifica la síntesis de importantes fármacos de ácido alquilo borónico y nuevos inhibidores de enzimas.

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Área de la Ciencia:

  • Química orgánica
  • Química medicinal
  • Catálisis

Sus antecedentes:

  • Los ácidos y ésteres alquilborónicos son productos intermedios sintéticos valiosos, pero su preparación es difícil.
  • Los métodos existentes para sintetizar estos compuestos a menudo implican procedimientos complejos o un alcance limitado.

Objetivo del estudio:

  • Desarrollar un método sencillo, práctico y de amplio alcance para la preparación de ésteres funcionalizados de alquilo boronato.
  • Aplicar este nuevo método a la síntesis de moléculas biológicamente relevantes, incluidos los productos farmacéuticos y los inhibidores de enzimas.

Principales métodos:

  • Se desarrolló una reacción catalizada por níquel para convertir derivados de ácido carboxílico en ésteres de boronato.
  • La reacción utiliza una estrategia de activación análoga a la formación de enlaces de amida.
  • El método se aplicó a la síntesis de péptidos y a la preparación de ácidos α-amino borónicos.

Principales resultados:

  • La reacción proporciona un acceso rápido a ésteres de boronato de alquilo densamente funcionalizados a partir de sustitutos carboxílicos abundantes.
  • Se facilitó la síntesis de los fármacos de ácido borónico alquilo Velcade y Ninlaro.
  • Se sintetizó un análogo de ácido borónico de la vancomicina con alta estereoselectividad.
  • Se descubrieron nuevos inhibidores potentes de la elastasa de los neutrófilos humanos con propiedades de unión covalente reversibles.

Conclusiones:

  • La reacción catalizada por níquel desarrollada ofrece una vía versátil y eficiente para los ésteres de boronato de alquilo.
  • Esta metodología simplifica significativamente la síntesis de compuestos farmacéuticos importantes y permite el descubrimiento de nuevos agentes bioactivos.
  • El método es prometedor para aplicaciones más amplias en síntesis orgánica y descubrimiento de fármacos.