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

8.7K
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.
8.7K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.3K
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...
8.3K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.7K
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.
18.7K
Electrophilic Aromatic Substitution: Nitration of Benzene01:20

Electrophilic Aromatic Substitution: Nitration of Benzene

6.3K
The nitration of benzene is an example of an electrophilic aromatic substitution reaction. It involves the formation of a very powerful electrophile, the nitronium ion, which is linear in shape. The reaction occurs through the interaction of two strong acids, sulfuric and nitric acid.
6.3K
Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

4.1K
Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
4.1K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.4K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.4K

You might also read

Related Articles

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

Sort by
Same author

Fluid-induced acid-base variations in postoperative critically ill patients: physiological determinants and renal response.

Frontiers in medicine·2026
Same author

Clinical outcome 24 months after cervical disc arthroplasty with a new articulating and viscoelastic disc prosthesis.

Journal of spine surgery (Hong Kong)·2026
Same author

Catalytic synthesis of saturated azacycles using transborylation.

Organic & biomolecular chemistry·2026
Same author

Vitamin C appears harmful in patients after out-of-hospital cardiac arrest treated in the intensive care unit.

Intensive care medicine·2026
Same author

Limiting neurodegeneration in ALS: A phosphatase paves the way.

Neuron·2026
Same author

Mitochondria limit coenzyme Q export under cholesterol biosynthetic stress.

The Journal of cell biology·2026

Related Experiment Video

Updated: Aug 25, 2025

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

2.9K

B-N/B-H Transborylation: borane-catalysed nitrile hydroboration.

Filip Meger1, Alexander C W Kwok1, Franziska Gilch1

  • 1EaStCHEM School of Chemistry, University of Edinburgh, Edinburgh, EH9 3FJ, United Kingdom.

Beilstein Journal of Organic Chemistry
|October 17, 2022
PubMed
Summary

A novel borane-catalyzed hydroboration converts nitriles into primary amines, offering a greener alternative to traditional methods. This reaction achieves good yields and selectivity, utilizing a unique double transborylation mechanism.

Keywords:
boroncatalysishydroborationnitriletransborylation

More Related Videos

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.7K
Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

8.8K

Related Experiment Videos

Last Updated: Aug 25, 2025

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

2.9K
Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants
08:56

Synthesis of 1,2-Azaborines and the Preparation of Their Protein Complexes with T4 Lysozyme Mutants

Published on: March 25, 2017

7.7K
Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides
08:46

Regioselective O-Glycosylation of Nucleosides via the Temporary 2',3'-Diol Protection by a Boronic Ester for the Synthesis of Disaccharide Nucleosides

Published on: July 26, 2018

8.8K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Nitrile reduction to primary amines is crucial in organic synthesis.
  • Existing methods often require stoichiometric reagents or transition-metal catalysts, posing environmental and cost concerns.

Purpose of the Study:

  • To develop a new, efficient, and selective method for the reduction of nitriles to primary amines.
  • To explore the use of borane catalysis for this transformation.

Main Methods:

  • Hydroboration of various nitriles using a borane catalyst.
  • Analysis of reaction yields and chemoselectivity.
  • Density Functional Theory (DFT) calculations and mechanistic studies to elucidate the reaction pathway.

Main Results:

  • Successful reduction of nitriles to primary amines with good yields (48-95%).
  • High chemoselectivity observed in the presence of other functional groups like esters, nitro, and sulfones.
  • Proposed a novel double B-N/B-H transborylation mechanism supported by computational and experimental data.

Conclusions:

  • Borane-catalyzed hydroboration provides an effective and selective route for synthesizing primary amines from nitriles.
  • The developed method offers a potentially more sustainable alternative to existing reduction techniques.
  • The proposed mechanism offers new insights into borane-mediated transformations.