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

8.3K
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.
8.3K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

3.3K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.3K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.8K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
7.8K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.2K
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.
18.2K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.2K
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...
8.2K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.1K
Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...
12.1K

You might also read

Related Articles

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

Sort by
Same author

Mapping mRNA Localization and Internal Structure in Lipid Nanoparticles through Solid-State Dynamic Nuclear Polarization NMR and Proton Spin-Diffusion Modeling.

Small methods·2026
Same author

Fluorinated Biradicals for <sup>19</sup>F Magic-Angle Spinning Dynamic Nuclear Polarization-Enhanced NMR Spectroscopy.

Journal of the American Chemical Society·2026
Same author

Corrigendum to "Experimental and computational <sup>17</sup>O solid-state NMR investigation of Na- and K-(bi)carbonate salts" [Solid State Nucl. Magn. Reson. 139 (2025) 102020].

Solid state nuclear magnetic resonance·2026
Same author

Correction: Capturing and labeling CO<sub>2</sub> in a jar: mechanochemical <sup>17</sup>O-enrichment and ssNMR study of sodium and potassium (bi)carbonate salts.

Chemical science·2025
Same author

Transforming solid-state nuclear magnetic resonance towards a chemistry-ready technique.

Solid state nuclear magnetic resonance·2025
Same author

Synthesis of Hydroxy-Functionalized Polyethylene via Radical Copolymerization of Ethylene with Alkenyl Boronate and Post-Polymerization Oxidation.

Angewandte Chemie (International ed. in English)·2025

Related Experiment Video

Updated: Jul 14, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.6K

Catalyst-Free Transfer Hydrogenation from Amine-Borane Small Oligomers.

Louis Le Moigne1, Tommaso Posenato2, David Gajan3

  • 1Univ Lyon, Université Claude Bernard Lyon 1, CNRS, CNES, ArianeGroup, LHCEP, UMR 5278, Bât. Raulin, 2 rue Victor Grignard, 69622, Villeurbanne, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|October 10, 2023
PubMed
Summary

New amine-borane oligomers efficiently catalyze transfer hydrogenations. These compounds bridge molecular reductants and polymers, offering insights into reactivity across different scales.

Keywords:
amine-boranesborondehydrogenationhydrogen transferoligomers

More Related Videos

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
08:40

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

Published on: December 6, 2021

3.6K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.2K

Related Experiment Videos

Last Updated: Jul 14, 2025

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes
12:08

Catalytic Reactions at Amine-Stabilized and Ligand-Free Platinum Nanoparticles Supported on Titania During Hydrogenation of Alkenes and Aldehydes

Published on: June 24, 2022

3.6K
Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production
08:40

Synthesis of Metal Nanoparticles Supported on Carbon Nanotube with Doped Co and N Atoms and its Catalytic Applications in Hydrogen Production

Published on: December 6, 2021

3.6K
A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
07:06

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

8.2K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Polymer Chemistry

Background:

  • Amine-borane complexes are valuable reducing agents.
  • Understanding the relationship between molecular structure and reactivity is crucial.
  • Polymeric amine-boranes have shown promise in catalysis.

Purpose of the Study:

  • To synthesize and characterize amine-borane dimers and oligomers with controlled properties.
  • To evaluate the catalytic activity of these compounds in transfer hydrogenation reactions.
  • To investigate the structural characteristics of post-reaction boron-containing materials.

Main Methods:

  • AA/BB polycondensation reactions controlled by capping agents.
  • Transfer hydrogenation of various unsaturated compounds (aldehydes, ketones, imines, alkenes, alkynes).
  • Solid-state Nuclear Magnetic Resonance (NMR) spectroscopy for material characterization.

Main Results:

  • Successfully prepared amine-borane dimers and oligomers with diverse steric and electronic profiles.
  • Demonstrated high catalytic efficiency in transfer hydrogenation, particularly with Lewis-paired oligomers and sterically hindered bis(amine-borane)s.
  • Observed enhanced reactivity attributed to facilitated dissociation and H-bond assistance in oligomers.
  • Confirmed structural similarity between materials from transfer dehydrogenation and thermal dehydrogenation via solid-state NMR.

Conclusions:

  • Amine-borane oligomers represent a key intermediate class between molecular reductants and poly-amine-boranes.
  • The developed synthetic strategy allows for tuning of amine-borane structures for optimized catalytic performance.
  • These findings provide a comprehensive understanding of reactivity trends in amine-borane systems at varying molecular scales.