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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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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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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

5.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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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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Preparation of Alcohols via Addition Reactions02:15

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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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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Una reacción general de tres componentes de alquilo petasa de boro-Mannich

Chao Hu1, Jet Tsien1, Si-Jie Chen2

  • 1Department of Biochemistry, The University of Texas Southwestern Medical Center, 5323 Harry Hines Blvd, Dallas, Texas 75390, United States.

Journal of the American Chemical Society
|July 29, 2024
PubMed
Resumen

Este estudio introduce una nueva reacción de tres componentes para sintetizar aminas complejas ricas en C ((sp3), cruciales para el descubrimiento de fármacos. El método permite la generación rápida de diversas bibliotecas de aminas para identificar posibles candidatos a fármacos.

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Área de la Ciencia:

  • Química medicinal
  • Síntesis orgánica

Sus antecedentes:

  • Las aminas arílicas prevalecen en las moléculas biológicamente activas, con el 37% de los fármacos candidatos que presentan aminas aromáticas.
  • Los avances en la química medicinal hacen hincapié en las aminas ricas en C ((sp3) para mejorar las propiedades farmacológicas.

Objetivo del estudio:

  • Para presentar una reacción modular y sencilla de tres componentes de alquilo Petasis boro-Mannich (APBM).
  • Para permitir el acceso rápido a diversas aminas complejas ricas en C ((sp3).

Principales métodos:

  • Utilizó una reacción de tres componentes que involucra aminas, aldehídos y boronatos de alquilo.
  • Adaptado la transformación para la experimentación de alto rendimiento (HTE).

Principales resultados:

  • Se ha demostrado una reacción modular y operacionalmente simple del APBM.
  • Se ha logrado una síntesis rápida de diversas aminas complejas ricas en C ((sp3) a través de HTE.

Conclusiones:

  • La reacción APBM proporciona un acceso eficiente a los valiosos bloques de construcción de aminas.
  • Este método acelera la identificación y el desarrollo de nuevos fármacos candidatos.