Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.4K
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.
9.4K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.6K
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...
8.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.3K
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.
19.3K
Halogenation of Alkenes02:46

Halogenation of Alkenes

16.9K
Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
16.9K
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

13.7K
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
13.7K
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

3.8K
Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
3.8K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Targeting the V-ATPase A Subunit in <i>Phytophthora sojae</i>: Discovery of Compound <b>A15</b>.

Journal of agricultural and food chemistry·2026
Same author

Study on the internal leakage pneumatic noise acoustic characteristics of spring-loaded full-lift safety valve.

Scientific reports·2026
Same author

A novel score to predict successful endovascular recanalization of non-acute carotid artery occlusion.

Journal of neurointerventional surgery·2026
Same author

Three Component Thio- and Carboboration of Alkynes: A Modular Route to Functionalised Bicyclic Boronates.

Angewandte Chemie (International ed. in English)·2026
Same author

Computationally and Target-Guided Discovery of Trifluoromethyl-Pyrazole Derivatives Targeting the a-c Subunit Interface of V-ATPase in <i>Phytophthora capsici</i>.

Journal of agricultural and food chemistry·2026
Same author

Succinate Dehydrogenase Subunits Differentially Regulate Physiology, SDHI Sensitivity, and DON Biosynthesis in <i>Fusarium pseudograminearum</i>.

Journal of agricultural and food chemistry·2026
Same journal

Spectroscopic, Thermal and Mass Spectrometry Investigations of Mechanochemically Synthesized Deep Eutectic Solvents.

New journal of chemistry = Nouveau journal de chimie·2026
Same journal

Photocontrolled immunotherapy: a BODIPY-caged MSA-2 for spatiotemporal activation of STING with visible light.

New journal of chemistry = Nouveau journal de chimie·2026
Same journal

Quantification of foscarnet with chromogenic and fluorogenic chemosensors: indicator displacement assays based on metal ion coordination with a catechol ligand moiety.

New journal of chemistry = Nouveau journal de chimie·2026
Same journal

Doxorubicin and Iron-doped Mesoporous Silica Nanoparticles for Chemodynamic Therapy and Chemotherapy of Breast Cancer.

New journal of chemistry = Nouveau journal de chimie·2025
Same journal

Synthesis of ferrocenyl benzimidazole derivatives as novel anti-<i>Toxoplasma gondii</i> agents.

New journal of chemistry = Nouveau journal de chimie·2024
Same journal

Supramolecular assembly of phenanthrene-DNA conjugates into light-harvesting nanospheres.

New journal of chemistry = Nouveau journal de chimie·2024
See all related articles

Related Experiment Video

Updated: Oct 21, 2025

Compact Lens-less Digital Holographic Microscope for MEMS Inspection and Characterization
10:28

Compact Lens-less Digital Holographic Microscope for MEMS Inspection and Characterization

Published on: July 5, 2016

10.5K

Haloboration: scope, mechanism and utility.

Sven Kirschner1, Kang Yuan1, Michael J Ingleson1

  • 1EaStCHEM School of Chemistry, University of Edinburgh Edinburgh EH9 3FJ UK michael.ingleson@ed.ac.uk.

New Journal of Chemistry = Nouveau Journal De Chimie
|September 6, 2021
PubMed
Summary
This summary is machine-generated.

Haloboration, the addition of boron halides across unsaturated bonds, offers controlled synthesis of valuable alkene building blocks. This review summarizes its history, mechanisms, and applications in natural products and materials science.

More Related Videos

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

69.2K
Construction of a High Resolution Microscope with Conventional and Holographic Optical Trapping Capabilities
09:12

Construction of a High Resolution Microscope with Conventional and Holographic Optical Trapping Capabilities

Published on: April 22, 2013

12.3K

Related Experiment Videos

Last Updated: Oct 21, 2025

Compact Lens-less Digital Holographic Microscope for MEMS Inspection and Characterization
10:28

Compact Lens-less Digital Holographic Microscope for MEMS Inspection and Characterization

Published on: July 5, 2016

10.5K
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
06:44

From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding

Published on: March 24, 2018

69.2K
Construction of a High Resolution Microscope with Conventional and Holographic Optical Trapping Capabilities
09:12

Construction of a High Resolution Microscope with Conventional and Holographic Optical Trapping Capabilities

Published on: April 22, 2013

12.3K

Area of Science:

  • Organic Chemistry
  • Organoboron Chemistry
  • Synthetic Methodology

Background:

  • Haloboration, the addition of boron halides (B-X) to unsaturated systems, is less explored than hydroboration.
  • It provides access to ambiphilic 1,2-disubstituted alkenes, particularly from alkynes.
  • These products are versatile synthons in organic synthesis and materials science.

Purpose of the Study:

  • To review the historical development of haloboration reactions.
  • To elucidate the current mechanistic understanding of haloboration.
  • To highlight recent advancements and applications of haloboration products.

Main Methods:

  • Literature review of haloboration reactions.
  • Analysis of mechanistic studies on haloboration.
  • Compilation of examples showcasing applications in synthesis and materials.

Main Results:

  • Haloboration of alkynes yields stereochemically controlled 1,2-disubstituted alkenes.
  • These alkenes serve as key intermediates in natural product synthesis.
  • Boron-doped polycyclic aromatic hydrocarbons (B-PAHs) are a significant application area.

Conclusions:

  • Haloboration is a powerful and controllable synthetic tool.
  • It enables the creation of complex molecules and novel materials.
  • Further exploration of haloboration chemistry is warranted for broader applications.