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

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

3.4K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.4K
Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

3.7K
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.
3.7K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

4.1K
Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
4.1K
Protection of Alcohols02:31

Protection of Alcohols

7.9K
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...
7.9K
Protecting Groups for Aldehydes and Ketones: Introduction01:23

Protecting Groups for Aldehydes and Ketones: Introduction

8.7K
Protecting groups are compounds that can bind to a specific functional group in the presence of other functional groups to protect them from undesired chemical reactions. These compounds can selectively bind to particular functional groups and advance chemoselective reactions in polyfunctional systems (Figure 1). After the functional group has served its purpose, it is removed by reacting it with specific compounds.
8.7K
Preparation of Amines: Alkylation of Ammonia and Amines01:30

Preparation of Amines: Alkylation of Ammonia and Amines

4.5K
Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.
Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering...
4.5K

You might also read

Related Articles

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

Sort by
Same author

An alkyl-swap platform for late-stage modification of secondary N-methylamines.

Nature chemistry·2026
Same author

Cation Sampling Enables Regiodivergent Distal Functionalization of Ketones.

Journal of the American Chemical Society·2026
Same author

Target-agnostic SAR mapping and immunological evaluation of (-)-FR252921 and analogs against primary human immune cells.

Chemical science·2026
Same author

Intrinsic N-Terminal Reactivity and Improved Analysis of DSSO-Carbamate and Carbamate-Based Cross-Linkers.

Analytical chemistry·2026
Same author

Facile (Z)-Selective Synthesis of β,γ-Unsaturated Ketones by a Silicon-based Olefination Strategy.

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

Synthesis of Sterically Congested Carbonyl Compounds via an <i>ipso</i>-Selective Sulfonium Rearrangement.

Journal of the American Chemical Society·2025

Related Experiment Video

Updated: Jan 8, 2026

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
06:44

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

Published on: April 6, 2017

10.1K

Deprotective Functionalization: An Emerging Concept for Amine Reactivity.

Irmgard Tiefenbrunner1, Saad Shaaban1, Nuno Maulide1

  • 1Faculty of Chemistry, Institute of Organic Chemistry, University of Vienna, Vienna, Austria.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 15, 2025
PubMed
Summary
This summary is machine-generated.

This study introduces deprotective functionalization, a novel synthetic strategy that converts protected functional groups directly into new ones. This approach avoids extra deprotection steps, reducing waste and enhancing synthetic efficiency for protected amines.

Keywords:
atom economycarbamatesdeprotective functionalizationsulfonamidesurea

More Related Videos

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.3K
Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

25.3K

Related Experiment Videos

Last Updated: Jan 8, 2026

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups
06:44

Hydrolysis of a Ni-Schiff-Base Complex Using Conditions Suitable for Retention of Acid-labile Protecting Groups

Published on: April 6, 2017

10.1K
Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron
07:56

Preparation of 6-aminocyclohepta-2,4-dien-1-one Derivatives via Tricarbonyltroponeiron

Published on: August 12, 2019

8.3K
Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology
11:42

Solid Phase Synthesis of a Functionalized Bis-Peptide Using "Safety Catch" Methodology

Published on: May 15, 2012

25.3K

Area of Science:

  • Organic Synthesis
  • Synthetic Chemistry

Background:

  • Protecting groups are essential in multi-step syntheses to control reactivity.
  • Conventional use of protecting groups adds steps, increases costs, and generates waste.
  • Late-stage deprotection of complex molecules presents significant challenges.

Purpose of the Study:

  • To introduce and conceptualize deprotective functionalization as an alternative to traditional protecting group strategies.
  • To demonstrate a method for directly converting protected functional groups into new functionalities without a separate deprotection step.
  • To explore the potential of protecting groups to actively participate in and direct chemical transformations.

Main Methods:

  • Conceptual framework development for deprotective functionalization.
  • Exploration of selective transformations of protected functional groups.
  • Focus on strategies applicable to protected amines.

Main Results:

  • Deprotective functionalization enables direct conversion of protected groups to new functionalities.
  • The protecting group acts not only as a shield but also as a directing group for transformations.
  • This approach bypasses the need for a distinct deprotection step, streamlining synthesis.

Conclusions:

  • Deprotective functionalization offers a more efficient and sustainable alternative to conventional protecting group methods.
  • This strategy minimizes synthetic steps, cost, and waste.
  • Current applications are demonstrated for protected amines, with potential for broader use.