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

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
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

18.0K
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.
18.0K
Protection of Alcohols02:31

Protection of Alcohols

7.3K
This lesson delves into the concept of protection and deprotection of a functional group fundamental to synthetic organic chemistry. These phenomena are explained in the context of aliphatic and aromatic alcohols.
Protection
It defines a protecting group as the masking agent to make the more reactive species inert to a given set of conditions. This concept is depicted via the illustration of liquid flow through different outlets in an assembly of pipes. The analogy helps to understand the role...
7.3K
Introduction to Functional Groups02:08

Introduction to Functional Groups

26.0K

Functional groups are group of atoms with specific chemical properties that occur within organic molecules and sometimes denoted as “R”. Functional groups are found along the carbon backbone of macromolecules can form chains or rings of carbon atoms. Functional groups can “functionalize” a compound by enabling it to adopt different physical and chemical properties.  
Types of common functional groups
The table below summarizes some of the major functional...
26.0K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.0K
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...
12.0K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

7.7K
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.
7.7K

You might also read

Related Articles

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

Sort by
Same author

Room-Temperature Metal-Catalyzed Hydrogen Borrowing Alkylation.

ACS catalysis·2026
Same author

Asymmetric Hydride Shift Reactions Catalyzed by Chiral Aluminium Complexes.

Angewandte Chemie (International ed. in English)·2025
Same author

A Divergent Asymmetric Total Synthesis of Coprophilin and Four Trichodermic Acids via a [1,5]-Hydride Shift-Aldol Cascade.

Journal of the American Chemical Society·2025
Same author

Indolequinone-Based Hypoxia-Activated Proteolysis Targeting Chimeras Selectively Degrade BRD4 in Hypoxic Cancer Cells.

Journal of the American Chemical Society·2025
Same author

Recent advances in the use of pentamethylphenyl (Ph*) ketones in organic synthesis.

Chemical communications (Cambridge, England)·2025
Same author

Visible Light-Promoted Construction of Cage-Like Frameworks by Sequential [2 + 2] Cycloaddition.

Organic letters·2025
Same journal

Chlorinated VSLSs Surpass HCFCs in CFC-11-Equivalent Emissions for Ozone Layer Depletion in China.

Nature communications·2026
Same journal

Author Correction: Charge transfer in triphenylamine-tetrazine covalent organic frameworks for solar-driven hydrogen peroxide production.

Nature communications·2026
Same journal

Vegetation browning patterns under compound soil and atmospheric dryness in northern permafrost ecosystems.

Nature communications·2026
Same journal

Voltage imaging of CA1 pyramidal cells and SST+ interneurons reveals stability and plasticity mechanisms of spatial firing.

Nature communications·2026
Same journal

Radical-omics reveals the hydrogen-abstraction pathway of isoprene oxidation.

Nature communications·2026
Same journal

Toughening elastomer via sequentially activated multi-pathway energy dissipation.

Nature communications·2026
See all related articles

Related Experiment Video

Updated: Jun 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K

Functional group tolerant hydrogen borrowing C-alkylation.

Elliot P Bailey1, Timothy J Donohoe2, Martin D Smith3

  • 1Chemistry Research Laboratory, University of Oxford, Oxford, UK.

Nature Communications
|June 15, 2024
PubMed
Summary
This summary is machine-generated.

This study introduces a new, milder method for hydrogen borrowing, a sustainable carbon-carbon bond formation technique. It allows for greater functional group tolerance at room temperature, expanding its utility in organic synthesis.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.0K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.4K

Related Experiment Videos

Last Updated: Jun 23, 2025

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
06:34

Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS

Published on: June 20, 2014

13.8K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.0K
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
06:46

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

Published on: June 21, 2017

7.4K

Area of Science:

  • Organic Chemistry
  • Sustainable Chemistry
  • Catalysis

Background:

  • Hydrogen borrowing enables alcohols to replace alkyl halides in C-C bond formation.
  • Current methods often require harsh conditions (high temperatures, strong bases), limiting functional group tolerance.

Purpose of the Study:

  • To develop a room temperature, functional group tolerant hydrogen borrowing methodology.
  • To expand the scope of alcohols usable in hydrogen borrowing reactions.

Main Methods:

  • Utilized a simple iridium catalyst under mild, substoichiometric basic conditions.
  • Employed anaerobic conditions to stabilize the iridium hydride intermediate.
  • Investigated reactivity at room temperature and moderately elevated temperatures.

Main Results:

  • Achieved room temperature hydrogen borrowing with high functional group tolerance.
  • Demonstrated successful reactions with previously incompatible alcohols.
  • Extended substrate scope to nitrogen-rich heterocycles using slightly elevated temperatures.

Conclusions:

  • Developed a milder, more versatile hydrogen borrowing protocol.
  • Anaerobic conditions are crucial for catalyst stability and high yields.
  • The methodology broadens the application of sustainable alcohol-based alkylation.