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

Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

5.7K
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
5.7K
Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate02:21

Oxidation of Alkenes: Syn Dihydroxylation with Potassium Permanganate

16.4K
Alkenes can be dihydroxylated using potassium permanganate.  The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
16.4K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

7.5K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
7.5K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride01:26

Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride

2.2K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.2K
Acid Halides to Carboxylic Acids: Hydrolysis01:01

Acid Halides to Carboxylic Acids: Hydrolysis

3.5K
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic...
3.5K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

12.6K
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.
12.6K

You might also read

Related Articles

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

Sort by
Same author

Unlocking Lewis acid-free metalation of O-nucleophiles in HFIP.

Communications chemistry·2026
Same author

Delayed Presentation Increases Complications After Catfish Spine Injuries.

Hand (New York, N.Y.)·2026
Same author

e-Carbonyl: Electrochemical Synthesis of α-Keto Esters via α-Carbonyl Carbocations.

Organic letters·2025
Same author

Alternating Current for Electrooxidative Nitroso Diels-Alder Reaction on 1,2-Dihydropyridines.

The Journal of organic chemistry·2025
Same author

Pharmacological Investigation of a Novel Resveratrol-like SIRT1 Activator Endowed with a Cardioprotective Profile.

Molecules (Basel, Switzerland)·2025
Same author

Functionalization of Electron-Rich Secondary Benzyl Alcohols in HFIP: From Thioethers to Trisubstituted Methanes.

The Journal of organic chemistry·2025

Related Experiment Video

Updated: Jan 18, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

10.1K

Potassium Hydroxide as a Cost-Effective Catalyst for Broad-Scope Silylation with TMSCF3.

Martyna Markwitz1, Kacper Łyczek1, Fabio Bellina2

  • 1Faculty of Chemistry, Adam Mickiewicz University, Poznań, Uniwersytetu Poznańskiego St. 8, 61-614 Poznań, Poland; https://www.kucinskilab.com.

The Journal of Organic Chemistry
|September 10, 2025
PubMed
Summary

A new silylation method uses trifluoromethyltrimethylsilane (TMSCF3) and potassium hydroxide (KOH) for efficient synthesis. This rapid and economical platform offers broad substrate scope and high functional group tolerance for organic chemistry applications.

More Related Videos

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.7K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.5K

Related Experiment Videos

Last Updated: Jan 18, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
09:37

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

10.1K
Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
08:25

Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs

Published on: January 17, 2020

7.7K
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
08:12

A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species

Published on: August 16, 2018

10.5K

Area of Science:

  • Synthetic organic chemistry
  • Organosilicon chemistry

Background:

  • Silylation is crucial in synthetic chemistry.
  • Traditional methods often use harsh reagents like chlorosilanes or hydrosilanes.
  • These reagents can be moisture-sensitive and corrosive.

Purpose of the Study:

  • To develop a novel, efficient, and broadly applicable silylation methodology.
  • To provide a simpler, faster, and more economical alternative to existing silylation techniques.

Main Methods:

  • Utilized trifluoromethyltrimethylsilane (TMSCF3) as a silylating agent.
  • Employed catalytic potassium hydroxide (KOH) to facilitate the reaction.
  • Investigated the reaction's applicability to various substrates, including terminal alkynes and alcohols.

Main Results:

  • Achieved high yields in silylation reactions.
  • Demonstrated operational simplicity, speed, and cost-effectiveness.
  • Showcased high functional group tolerance across a broad substrate scope.
  • Successfully silylated pharmaceutically relevant molecules.

Conclusions:

  • The TMSCF3/KOH system provides an efficient and versatile platform for silylation.
  • This method overcomes limitations of traditional silylation reagents.
  • The developed methodology is suitable for synthesizing diverse organic molecules, including those with pharmaceutical relevance.