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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

6.4K
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

20.6K
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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BX3-Mediated Arene Borylation: Concepts, Scope, and Mechanistic Insight.

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
Summary

Transition metal-free arene C‒H borylation offers a sustainable route to arylborane synthesis using boron trihalides. This review analyzes the mechanisms of these metal-free reactions for future methodology development.

Keywords:
C‒H borylationSEArboron trihalideorganoborontransition metal‐free

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Sustainable Chemistry

Background:

  • Precious metal-catalyzed borylation reactions present limitations.
  • Transition metal-free arene C‒H borylation offers a sustainable alternative.
  • Electrophilic boron trihalides are key reagents in metal-free borylation.

Purpose of the Study:

  • To critically analyze the mechanistic pathways of transition metal-free arene C‒H borylation.
  • To emphasize the elementary steps in BX3-mediated C-H bond functionalization.
  • To provide a framework for interpreting existing studies and designing future methods.

Main Methods:

  • Review of existing literature on metal-free borylation.
  • Mechanistic analysis of BX3-mediated C-H functionalization.
  • Focus on electrophilic activation of arene π-electron systems.

Main Results:

  • Detailed examination of mechanistic pathways in metal-free borylation.
  • Identification of key elementary steps in BX3-mediated reactions.
  • Conceptual framework for understanding and designing borylation methodologies.

Conclusions:

  • Transition metal-free borylation is a viable and sustainable synthetic strategy.
  • Understanding mechanistic pathways is crucial for optimizing these reactions.
  • This review provides insights for advancing metal-free borylation chemistry.