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

9.6K
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.
9.6K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

22.1K
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.
22.1K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

4.4K
Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction...
4.4K
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

4.8K
Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide...
4.8K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.3K
Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
2.3K
Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

5.3K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
5.3K

You might also read

Related Articles

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

Sort by
Same author

Late-stage generation of <sup>14</sup>C/<sup>3</sup>H-radiolabeled lysine residues via hydroformylation of peptides.

Nature communications·2026
Same author

Palladacarboxamide Capping Reagents for Carbon Isotope Labeling and Pharmaceutical Diversification.

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

Effects of Exogenous Inoculation on Microbial Community Dynamics and Maturation Process in Cattle Manure Composting.

Microorganisms·2026
Same author

Insights Into CO<sub>2</sub> Loss, pH Effects, and Tafel Kinetics in Ni Single Atom-Driven Bicarbonate Electroreduction.

Advanced science (Weinheim, Baden-Wurttemberg, Germany)·2026
Same author

Nonporous hydrophobic organic crystals for carbon dioxide capture via chain-melting phase transition.

Nature communications·2026
Same author

Co<sub>3</sub>O<sub>4</sub>‑Promoted Cerium Oxide Catalyst for Efficient Catalytic <i>N</i>‑Alkylation of Amines with Alcohols.

ACS organic & inorganic Au·2025

Related Experiment Video

Updated: Apr 14, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K

Organocatalyzed CO2 Trapping Using Alkynyl Indoles.

Zhuo Xin1, Camille Lescot1, Stig D Friis1

  • 1Carbon Dioxide Activation Center (CADIAC), Interdisciplinary Nanoscience Center (iNANO) and Department of Chemistry, Aarhus University, Gustav Wieds Vej 14, 8000 Aarhus (Denmark) http://www.skrydstrup-group.com.

Angewandte Chemie (International Ed. in English)
|April 25, 2015
PubMed
Summary

Researchers developed the first organocatalyzed method to trap carbon dioxide (CO2) using alkynyl indoles. This novel approach efficiently creates new heterocyclic compounds under mild conditions.

Keywords:
carbon dioxideheterocycleslactonesorganocatalysissynthetic methods

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

8.5K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

11.4K

Related Experiment Videos

Last Updated: Apr 14, 2026

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones
07:30

A Direct, Regioselective and Atom-Economical Synthesis of 3-Aroyl-N-hydroxy-5-nitroindoles by Cycloaddition of 4-Nitronitrosobenzene with Alkynones

Published on: January 21, 2020

8.8K
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

8.5K
Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
12:27

Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes

Published on: September 8, 2013

11.4K

Area of Science:

  • Organic Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Carbon dioxide (CO2) utilization remains a significant challenge in chemistry.
  • Developing efficient catalytic systems for CO2 transformation is crucial for sustainable synthesis.
  • Heterocyclic compounds are vital structural motifs in pharmaceuticals and materials.

Purpose of the Study:

  • To report the first organocatalyzed method for trapping CO2 via C-C and C-O bond formation.
  • To synthesize novel indole-containing heterocyclic structures using CO2 as a C1 building block.
  • To explore the scope and mechanism of this new synthetic transformation.

Main Methods:

  • Utilizing alkynyl indoles as substrates.
  • Employing catalytic amounts of an organic base.
  • Reacting with stoichiometric amounts of carbon dioxide (CO2).
  • Employing mild reaction conditions.

Main Results:

  • Successful synthesis of new tricyclic indole-containing heterocyclic structures.
  • Demonstrated complete regioselectivity in the formation of products.
  • Showcased the reaction's applicability to aromatic, heteroaromatic, and aliphatic alkynyl indoles.
  • Identified C-C bond formation as the initial intermolecular step, followed by C-O bond formation (lactone formation).

Conclusions:

  • This study presents a pioneering organocatalyzed strategy for CO2 fixation.
  • The developed method offers a sustainable and efficient route to valuable heterocyclic compounds.
  • The findings pave the way for new CO2 utilization pathways in organic synthesis.