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

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.7K
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 halogen to form a...
3.7K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.2K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.2K
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

5.8K
Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
5.8K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

2.8K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
2.8K
Acid-Catalyzed Aldol Addition Reaction01:15

Acid-Catalyzed Aldol Addition Reaction

2.5K
The aldol reaction of a ketone under acidic conditions successfully forms an unsaturated carbonyl as the final product instead of an aldol. The acid-catalyzed aldol reaction is depicted in Figure 1.
2.5K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

10.1K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
10.1K

You might also read

Related Articles

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

Sort by
Same author

Diastereoselective Synthesis of Housanes via the Carbocupration of Cyclopropenes.

Journal of the American Chemical Society·2026
Same author

Access to Regiodefined Tetrahydrofuran-3-one-Derived C-2 Silyl Enol Ethers from α-Triisopropylsilyl-α-diazoketones: The TIPS Trick.

Organic letters·2026
Same author

Ultrasound-guided removal of a splenic foreign body in a dog.

The Canadian veterinary journal = La revue veterinaire canadienne·2024
Same author

TIPS-Diazoacetone Aldol Addition: Mechanistic Aspects and Contribution to the Synthesis.

The Journal of organic chemistry·2021
Same author

Cobalt-Catalyzed 1,4-Aryl Migration/Desulfonylation Cascade: Synthesis of α-Aryl Amides.

Chemistry (Weinheim an der Bergstrasse, Germany)·2020
Same author

Copper-Catalyzed Cross-Coupling between Alkyl (Pseudo)halides and Bicyclopentyl Grignard Reagents.

Organic letters·2020

Related Experiment Video

Updated: Jun 26, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.7K

Iron-Catalyzed, Light-Driven Decarboxylative Alkoxyamination.

Milan Innocent1, Clément Tanguy1, Sigrid Gavelle1

  • 1Molecular, Macromolecular Chemistry and Materials, ESPCI Paris - PSL, CNRS, 10 rue Vauquelin, 75005, Paris, France.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 13, 2024
PubMed
Summary

This study introduces an iron-catalyzed reaction using visible light to convert carboxylic acids into alkoxyamine derivatives. This versatile method enables molecular diversity from readily available starting materials.

Keywords:
LMCTalkoxyaminationdecarboxylationironphotocatalysis

More Related Videos

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

10.9K
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 26, 2025

Light-driven Enzymatic Decarboxylation
09:58

Light-driven Enzymatic Decarboxylation

Published on: May 22, 2016

11.7K
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

10.9K
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
  • Catalysis
  • Photochemistry

Background:

  • Carboxylic acids are abundant starting materials.
  • Functionalization of carboxylic acids remains a challenge.
  • Decarboxylative reactions offer efficient synthetic routes.

Purpose of the Study:

  • To develop a novel iron-catalyzed visible-light driven decarboxylative alkoxyamination.
  • To demonstrate the broad substrate scope including drugs and biobased molecules.
  • To provide a general approach for functionalization.

Main Methods:

  • Utilizing iron(II) bromide (FeBr2) as a catalyst.
  • Employing TEMPO as a co-catalyst/mediator.
  • Employing visible light irradiation for the reaction.

Main Results:

  • Successful synthesis of diverse alkoxyamine derivatives from various carboxylic acids.
  • Demonstrated applicability to marketed drugs and biobased molecules.
  • Established a unified and general method for decarboxylative functionalization.

Conclusions:

  • The developed method is a versatile and efficient approach for generating molecular diversity.
  • This work expands the utility of iron catalysis in photoredox reactions.
  • The protocol offers a sustainable route using abundant starting materials and a common catalyst.