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

12.3K
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.
12.3K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

21.9K
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.
21.9K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

9.7K
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.
9.7K
Radical Anti-Markovnikov Addition to Alkenes: Mechanism01:17

Radical Anti-Markovnikov Addition to Alkenes: Mechanism

5.1K
The reaction of hydrogen bromide with alkenes in the presence of hydroperoxides or peroxides proceeds via anti-Markovnikov addition. The radical chain reaction comprises initiation, propagation, and termination steps.
The mechanism starts with chain initiation, which involves two steps. In the first chain initiation step, a weak peroxide bond is homolytically cleaved upon mild heating to form two alkoxy radicals. In the second initiation step, a hydrogen atom is abstracted by the alkoxy...
5.1K
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

12.1K
Electrophilic addition of hydrogen halides, HX (X = Cl, Br or I) to alkenes forms alkyl halides as per Markovnikov's rule, where the hydrogen gets added to the less substituted carbon of the double bond. Hydrohalogenation of alkynes takes place in a similar manner, with the first addition of HX forming a vinyl halide and the second giving a geminal dihalide.
12.1K

You might also read

Related Articles

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

Sort by
Same author

An N-heterocyclic <i>N</i>-isocyanoguanidine: an uncommonly strong σ donating isocyanide ligand.

Chemical communications (Cambridge, England)·2026
Same author

Metrology of rare earths and other elements in waste fluorescent lamp powder - A methodological comparison.

Analytica chimica acta·2026
Same author

Organophosphinidene in a T-Shaped Environment.

Journal of the American Chemical Society·2026
Same author

Hidden environmental and energy impacts of high-performance MOFs for ammonia removal: Life cycle insights toward sustainable design.

Journal of environmental management·2026
Same author

Movement of dimethylsilanediol formed in-situ from octamethylcyclotetrasiloxane in soil - A combined experimental and modeling study.

The Science of the total environment·2026
Same author

Metal-Free Catalytic Cross-Coupling of Esters and Boranes.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Mar 29, 2026

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

7.0K

Reversible hydrogen activation by a bulky haloborane based FLP system.

Marc-André Courtemanche1, Étienne Rochette, Marc-André Légaré

  • 1Département de Chimie, Université Laval, 1045 Avenue de la Médecine, Québec, Québec, CanadaG1 V 0A6. Frederic.fontaine@chm.ulaval.ca.

Dalton Transactions (Cambridge, England : 2003)
|November 25, 2015
PubMed
Summary

A novel monomeric Frustrated Lewis Pair (FLP), bis(2-(2,2,6,6-tetramethylpiperidine)phenyl)chloroborane, was synthesized. This FLP reversibly activates H2 and can generate a new FLP species upon base treatment.

More Related Videos

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

16.1K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.6K

Related Experiment Videos

Last Updated: Mar 29, 2026

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
10:10

Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes

Published on: July 28, 2018

7.0K
Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia
12:05

Preparation of Hydrophobic Metal-Organic Frameworks via Plasma Enhanced Chemical Vapor Deposition of Perfluoroalkanes for the Removal of Ammonia

Published on: October 10, 2013

16.1K
Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

3.6K

Area of Science:

  • Organoboron chemistry
  • Frustrated Lewis Pair (FLP) chemistry
  • Hydrogen activation

Background:

  • Frustrated Lewis Pairs (FLPs) are Lewis acids and bases that do not interact due to steric hindrance.
  • FLPs are known for their ability to activate small molecules like H2.
  • Monomeric FLPs are less common and offer unique reactivity.

Purpose of the Study:

  • To synthesize and characterize a novel monomeric FLP species.
  • To investigate the H2 activation capabilities of the synthesized FLP.
  • To explore the reactivity of the H2 activation product with a base.

Main Methods:

  • Synthesis and single-crystal X-ray diffraction of bis(2-(2,2,6,6-tetramethylpiperidine)phenyl)chloroborane.
  • Spectroscopic characterization (NMR, IR) of reactants and products.
  • Reactivity studies involving H2 gas and a base.

Main Results:

  • The monomeric FLP, bis(2-(2,2,6,6-tetramethylpiperidine)phenyl)chloroborane (1), was successfully prepared and crystallized, showing no B-N interaction.
  • Species 1 reversibly reacts with H2 at room temperature to form a zwitterionic H2 activation product (2).
  • Treatment of product 2 with a base releases HCl, yielding a new monomeric FLP species (3).

Conclusions:

  • A novel monomeric FLP was synthesized, demonstrating effective H2 activation.
  • The FLP system exhibits reversible H2 activation and can be further functionalized.
  • This work expands the scope of monomeric FLP chemistry and their applications in small molecule activation.