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 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.
Electrophilic Addition to Alkynes: Hydrohalogenation02:35

Electrophilic Addition to Alkynes: Hydrohalogenation

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.
Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
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.
Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
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...

You might also read

Related Articles

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

Sort by
Same author

Controlled Amine-Borane Dehydropolymerization Enabled by Mechanistic Insight Using the Ir(<sup>t</sup>Bu-POCOP)H<sub>2</sub> Catalyst.

Journal of the American Chemical Society·2026
Same author

N-Alkoxysulfurdiimide Reagents for the One-Step Modular Synthesis of Primary Sulfonimidamides.

Angewandte Chemie (International ed. in English)·2026
Same author

The palladium-catalysed modular annulative synthesis of cyclic sulfonimidamides.

Chemical science·2026
Same author

The characterisation and reactivity of a Rh<sup>iii</sup> η<sup>1</sup>-σ-alkane complex and the role of a structurally responsive phosphine ligand in solid-state molecular organometallic chemistry.

Chemical science·2026
Same author

Solid-state molecular organometallic chemistry (SMOM): a user guide to <i>in crystallo</i> single-crystal to single-crystal transformations using solid/gas methods.

Dalton transactions (Cambridge, England : 2003)·2026
Same author

Synthesis, Functionalization, and Reactivity of Vinyl Sulfondiimidamides.

Angewandte Chemie (International ed. in English)·2026
Same journal

3-Methyleneazetidine: a versatile building block for functional and post-modifiable polysulfonamides.

Chemical communications (Cambridge, England)·2026
Same journal

Synthesis of divalent galactosyl and fucosyl spiropyran derivatives for the targeted inhibition of bacterial biofilms.

Chemical communications (Cambridge, England)·2026
Same journal

Emergent cytotoxicity and mitochondrial alterations induced by a heterobimetallic Re(I)/Au(I) complex.

Chemical communications (Cambridge, England)·2026
Same journal

Cyanoacetylation of amines <i>via</i> a traceless cyanoacetyl radical: synthetic access to teriflunomide.

Chemical communications (Cambridge, England)·2026
Same journal

Loading layered double hydroxide nanoarray catalysts on a micro-curved substrate for kinetics-favorable water electrolysis reaction.

Chemical communications (Cambridge, England)·2026
Same journal

Bridging <i>in situ</i> measurements and practical conditions through gas-liquid management for CO/CO<sub>2</sub> reduction.

Chemical communications (Cambridge, England)·2026
See all related articles

Related Experiment Video

Updated: May 22, 2026

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

Rhodium-catalysed linear-selective alkyne hydroacylation.

Sarah-Jane Poingdestre1, Jonathan D Goodacre, Andrew S Weller

  • 1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK. michael.willis@chem.ox.ac.uk.

Chemical Communications (Cambridge, England)
|May 24, 2012
PubMed
Summary
This summary is machine-generated.

This study introduces an efficient method for hydroacylative coupling using the diphosphine ligand, dcpe. This process selectively joins aldehydes and alkynes, offering a new synthetic route.

More Related Videos

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

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Related Experiment Videos

Last Updated: May 22, 2026

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

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

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
09:54

Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes

Published on: September 12, 2018

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Organometallic Chemistry

Background:

  • Hydroacylative coupling is a key reaction in organic synthesis.
  • Developing efficient and selective catalytic systems remains a challenge.

Purpose of the Study:

  • To develop an efficient and highly linear selective hydroacylative coupling reaction.
  • To utilize the electron-rich diphosphine ligand, 1,2-bis(dicyclohexylphosphino)ethane (dcpe), as a catalyst.

Main Methods:

  • The reaction employed aldehydes (including aryl aldehydes) and alkynes.
  • The electron-rich diphosphine ligand, dcpe, was used to facilitate the coupling.

Main Results:

  • The study achieved efficient and highly linear selective hydroacylative coupling.
  • The reaction demonstrated broad applicability with various aldehydes and alkynes.

Conclusions:

  • The use of dcpe enables efficient and selective hydroacylative coupling.
  • This method provides a valuable tool for synthesizing complex organic molecules.