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Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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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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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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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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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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α-Alkylation of Ketones via Enolate Ions01:10

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Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
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Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene01:13

Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene

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Bromination and chlorination of aromatic rings by electrophilic aromatic substitution reactions are easily achieved, but fluorination and iodination are difficult to achieve. Fluorine is so reactive that its reaction with benzene is difficult to control, resulting in poor yields of monofluoroaromatic products. To address this, Selectfluor reagent is used as a fluorine source in which a fluorine atom is bonded to a positively charged nitrogen.
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Updated: Nov 7, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Light-induced borylation: developments and mechanistic insights.

Dipti Lai1, Sumit Ghosh1, Alakananda Hajra1

  • 1Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India. alakananda.hajra@visva-bharati.ac.in.

Organic & Biomolecular Chemistry
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Summary

Eco-friendly light-induced borylation offers a green chemistry approach to synthesize organoboron compounds. This review covers UV- and visible-light strategies from the last decade, detailing reaction mechanisms.

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Area of Science:

  • Organic Chemistry
  • Green Chemistry
  • Synthetic Methodology

Background:

  • Organoboron compounds are crucial in medicinal, biological, and industrial applications.
  • Novel borylation methodologies are of significant interest to synthetic chemists.
  • Traditional borylation methods may not always align with green chemistry principles.

Purpose of the Study:

  • To review UV- and visible-light-induced borylation strategies developed over the past decade.
  • To highlight the importance of eco-friendly borylation methods.
  • To provide insights into the reaction mechanisms of these light-induced borylation processes.

Main Methods:

  • Comprehensive literature search for light-induced borylation reactions.
  • Categorization of borylation strategies based on light source (UV/visible).
  • Analysis of reaction mechanisms and green chemistry aspects.

Main Results:

  • Numerous UV- and visible-light-induced borylation methods have emerged in the last 10 years.
  • These light-mediated reactions offer sustainable routes to organoboronic esters and acids.
  • Understanding the mechanisms enhances the development of new synthetic protocols.

Conclusions:

  • Light-induced borylation represents a powerful and green synthetic tool.
  • Continued research in this area promises further advancements in organoboron compound synthesis.
  • These methodologies are vital for sustainable chemical synthesis.