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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 stereochemistry.
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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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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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Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene01:15

Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene

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Chlorination and bromination are important classes of electrophilic aromatic substitutions, where benzene reacts with chlorine or bromine in the presence of a Lewis acid catalyst to give halogenated substitution products. A Lewis acid such as aluminium chloride or ferric chloride catalyzes the chlorination, and ferric bromide catalyzes the bromination reactions. During the bromination of alkenes, bromine polarizes and becomes electrophilic. However, in the bromination of benzene, the bromine...
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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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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Borilación de Arenos Mediada por BX₃: Conceptos, Alcance e Perspectiva Mecanicista

Rahul Bangari1, Rudraa Singh Rajpoot1, Naoto Chatani2,3

  • 1Department of Chemistry, IIT Dharwad, Chikka Malligwad, Karnataka, India.

Chemistry, an Asian journal
|December 21, 2025
PubMed
Resumen

La borilación C-H de arenos sin metales de transición ofrece una ruta sostenible para la síntesis de arilboranos utilizando trihaluros de boro. Esta revisión analiza los mecanismos de estas reacciones sin metales para el desarrollo de metodologías futuras.

Palabras clave:
borilación C-HSEArtrihaluro de boroorganoboranosin metales de transición

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Área de la Ciencia:

  • Química Orgánica
  • Catálisis
  • Química Sostenible

Sus antecedentes:

  • Las reacciones de borilación catalizadas por metales preciosos presentan limitaciones.
  • La borilación C-H de arenos sin metales de transición ofrece una alternativa sostenible.
  • Los trihaluros de boro electrófilos son reactivos clave en la borilación sin metales.

Objetivo del estudio:

  • Analizar críticamente las vías mecanísticas de la borilación C-H de arenos sin metales de transición.
  • Enfatizar los pasos elementales en la funcionalización C-H mediada por BX₃.
  • Proporcionar un marco para interpretar estudios existentes y diseñar métodos futuros.

Principales métodos:

  • Revisión de la literatura existente sobre borilación sin metales.
  • Análisis mecanístico de la funcionalización C-H mediada por BX₃.
  • Enfoque en la activación electrófila de los sistemas de electrones π de los arenos.

Principales resultados:

  • Examen detallado de las vías mecanísticas en la borilación sin metales.
  • Identificación de los pasos elementales clave en las reacciones mediadas por BX₃.
  • Marco conceptual para comprender y diseñar metodologías de borilación.

Conclusiones:

  • La borilación sin metales de transición es una estrategia sintética viable y sostenible.
  • La comprensión de las vías mecanísticas es crucial para optimizar estas reacciones.
  • Esta revisión proporciona información para avanzar en la química de borilación sin metales.