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

Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

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.
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.
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

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 surface of...
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...
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.
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

You might also read

Related Articles

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

Sort by
Same author

From complexity to approval in the European Union: Regulatory pathways and data challenges in the evaluation of non-oncology orphan medicines.

Drug discovery today·2026
Same author

[Correction: Development of a standardized handover for critically ill premature and newborn infants for interhospital transport in Bavaria].

Zeitschrift fur Geburtshilfe und Neonatologie·2025
Same author

[Development of a standardized handover for critically ill premature and newborn infants for interhospital transport in Bavaria].

Zeitschrift fur Geburtshilfe und Neonatologie·2025
Same author

Studies on the Effect of Positive and Negative Charges on the <sup>77</sup>Se NMR Shifts of Selenones and Selenenyls of N-heterocyclic Carbenes of Imidazolium-4,5-dicarboxylates.

The Journal of organic chemistry·2025
Same author

Anionic N-Heterocyclic Carbenes from Mesoionic Imidazolium-4-pyrrolides: The Influence of Substituents, Solvents, and Charge on their <sup>77</sup>Se NMR Chemical Shifts.

The Journal of organic chemistry·2024
Same author

Real-World Evidence to Support EU Regulatory Decision Making-Results From a Pilot of Regulatory Use Cases.

Clinical pharmacology and therapeutics·2024

Related Experiment Video

Updated: Jun 10, 2026

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

The hydroarylation reaction--scope and limitations.

Jan C Namyslo1, Jörg Storsberg, Jens Klinge

  • 1Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, D-38678 Clausthal-Zellerfeld, Germany.

Molecules (Basel, Switzerland)
|July 27, 2010
PubMed
Summary
This summary is machine-generated.

This study explores palladium-catalyzed reactions for synthesizing complex molecules. It details stereoselective hydroarylation and domino-Heck reactions using novel ligands and cyclic alkenes.

More Related Videos

Biomass Conversion to Produce Hydrocarbon Liquid Fuel Via Hot-vapor Filtered Fast Pyrolysis and Catalytic Hydrotreating
11:28

Biomass Conversion to Produce Hydrocarbon Liquid Fuel Via Hot-vapor Filtered Fast Pyrolysis and Catalytic Hydrotreating

Published on: December 25, 2016

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

Related Experiment Videos

Last Updated: Jun 10, 2026

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

Biomass Conversion to Produce Hydrocarbon Liquid Fuel Via Hot-vapor Filtered Fast Pyrolysis and Catalytic Hydrotreating
11:28

Biomass Conversion to Produce Hydrocarbon Liquid Fuel Via Hot-vapor Filtered Fast Pyrolysis and Catalytic Hydrotreating

Published on: December 25, 2016

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

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Palladium-catalyzed reactions are crucial for C-C and C-heteroatom bond formation.
  • Stereoselective synthesis of complex molecules remains a significant challenge in organic chemistry.
  • Developing efficient ligands is key to controlling reactivity and selectivity in catalysis.

Purpose of the Study:

  • To investigate the synthetic potential of stereoselective palladium-catalyzed hydro(het)arylation reactions.
  • To explore the mechanistic intricacies of these reactions with various polycyclic alkenes.
  • To develop novel synthetic routes to complex organic scaffolds.

Main Methods:

  • Palladium-catalyzed reactions utilizing phosphine and arsine ligands.
  • Hydroarylation of bi-, tri-, and tetracyclic (hetero)alkenes.
  • Mechanistic studies involving electron-deficient arylpalladium complexes and different alkene structures.

Main Results:

  • Stereoselective hydroarylation of diazabicyclo-[2.2.1]heptenes yielding aryldiaminocyclopentanes.
  • Observation of a formal 1,2-hydrazidoarylation reaction with 1,3-cyclopentadiene.
  • Differential reactivity based on alkene rigidity (bicyclo[2.2.1]heptenes vs. bicyclo[2.2.2]octenes).
  • Induction of domino-Heck reactions in more flexible systems like bicyclo[4.2.2]decenes.
  • First report of a pi,sigma domino-Heck reaction involving carbopalladation of a tetracyclic cis-allylcyclopropane.

Conclusions:

  • Phospine and arsine ligands enable efficient stereoselective palladium-catalyzed hydro(het)arylation.
  • Reaction mechanisms vary with substrate structure, leading to diverse products.
  • The study expands the scope of palladium catalysis for complex molecule synthesis.