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Videos de Conceptos Relacionados

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.
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.
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.
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...
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy radical...
Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.

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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Hidroboración intramolecular dirigida por oxígeno dirigida por oxígeno.

Robert-André F Rarig1, Matthew Scheideman, Edwin Vedejs

  • 1Department of Chemistry, University of Michigan, Ann Arbor, Michigan 48109, USA.

Journal of the American Chemical Society
|June 25, 2008
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un método de hidroboración intramolecular libre de metales para los alcoholes homoalílicos. El proceso logra una alta regioselectividad para los productos sustituidos por 1,3-dióxido, mejorada por la ramificación C5.

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Área de la Ciencia:

  • Química orgánica es la química orgánica.
  • Química sintética de la química sintética.
  • La catálisis de la catálisis.

Sus antecedentes:

  • La hidroboración intramolecular es una transformación sintética clave.
  • El desarrollo de sistemas catalíticos libres de metales es un objetivo importante en la síntesis orgánica.
  • Dirigir las estrategias de grupo es crucial para controlar la selectividad regional.

Objetivo del estudio:

  • Para informar sobre una nueva hidroboración intramolecular dirigida por oxígeno homoalílico libre de metales y dirigida por oxígeno.
  • Para lograr una alta regioselectividad en la hidroboración de alcoholes homoalílicos.
  • Para investigar el efecto de la ramificación del sustrato en la regioselectividad.

Principales métodos:

  • Se utilizó un sistema libre de metales que empleaba sulfuro de dimetilo borano (Me2S.BH3) y ácido trifílico (TfOH).
  • Se empleó hidroboración intramolecular dirigida por oxígeno de alcoholes homoalílicos.
  • Se realiza el procesamiento oxidativo estándar para obtener los productos finales.

Principales resultados:

  • Logró altas regioselectividades que van desde 20:1 hasta 82:1.
  • Demostró una fuerte preferencia por la formación de productos sustituidos por 1,3-dióxido.
  • Se observó que la ramificación en la posición C5 del sustrato mejora significativamente la regioselectividad.

Conclusiones:

  • El método desarrollado ofrece una ruta eficiente y selectiva a valiosos compuestos orgánicos oxigenados.
  • Este enfoque libre de metales proporciona una alternativa más ecológica a los métodos tradicionales de hidroboración.
  • Las modificaciones estructurales del sustrato, como la ramificación C5, pueden emplearse estratégicamente para mejorar los resultados de la reacción.