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Related Concept Videos

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.
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.
Hybridization of Atomic Orbitals I03:24

Hybridization of Atomic Orbitals I

The mathematical expression known as the wave function, ψ, contains information about each orbital and the wavelike properties of electrons in an isolated atom. When atoms are bound together in a molecule, the wave functions combine to produce new mathematical descriptions that have different shapes. This process of combining the wave functions for atomic orbitals is called hybridization and is mathematically accomplished by the linear combination of atomic orbitals. The new orbitals that...
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.
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction01:15

α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction

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 bromine molecule...
Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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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Updated: Jun 20, 2026

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Published on: November 30, 2022

Bisphosphane-Stabilized Borylenes: Unlocking Borylene Transfer Reactivities.

Zimeng Zhang1, Shuyan Liu1, Kai Lu1

  • 1Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University, Renai Road 199, Suzhou, Jiangsu Province, P. R. China.

Angewandte Chemie (International Ed. in English)
|June 18, 2026
PubMed
Summary
This summary is machine-generated.

Researchers developed stable borylenes for efficient boron-containing compound synthesis. These novel reagents demonstrate exceptional borylene-transfer capabilities, overcoming previous limitations in boron chemistry.

Keywords:
ambiphilicityboroniumboryleneorganoboronumpolung

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Area of Science:

  • Organometallic Chemistry
  • Synthetic Chemistry
  • Boron Chemistry

Background:

  • Borylene-transfer reactions are crucial for synthesizing boron compounds but lack reliable reagents.
  • A key challenge is stabilizing highly reactive borylenes for practical use.

Purpose of the Study:

  • To synthesize and characterize novel bisphosphane-stabilized borylenes.
  • To evaluate their efficacy as borylene-transfer reagents.

Main Methods:

  • Synthesis of borylenes via deprotonation of hydroboronium precursors using potassium bis(trimethylsilyl)amide.
  • Borylene-transfer reactions with hydroboranes, benzaldehyde, and chalcone.
  • Experimental and computational studies to elucidate reaction mechanisms.

Main Results:

  • Successfully synthesized bisphosphane-stabilized borylenes.
  • Demonstrated efficient borylene transfer, including B─H bond insertion and transfer to polar π systems.
  • Identified labile phosphorus-boron coordination as key to reactivity.

Conclusions:

  • Stable hydroboronium compounds can serve as precursors for effective borylene-transfer reagents.
  • This work expands the toolkit for constructing complex boron-containing molecules.