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Related Concept Videos

Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

2.6K
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...
2.6K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.9K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.9K
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

6.2K
All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
6.2K
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

4.1K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.1K
Directing Effect of Substituents: ortho–para-Directing Groups01:14

Directing Effect of Substituents: ortho–para-Directing Groups

6.7K
Ortho–para directors are substituent groups attached to the benzene ring and direct the addition of an electrophile to the positions ortho or para to the substituent. All electron-donating groups are considered ortho–para directors. They donate electrons to the ring and make the ring more electron-rich. The ring is therefore susceptible to the addition of electrophiles. Substituents such as amino, hydroxy, or alkoxy, containing lone pairs on the atom adjacent to the ring, donate...
6.7K
Preparation of Amides01:29

Preparation of Amides

3.2K
Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
3.2K

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Related Experiment Video

Updated: Aug 3, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
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Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.8K

Amides as modifiable directing groups in electrophilic borylation.

Saqib A Iqbal1, Marina Uzelac1, Ismat Nawaz1,2

  • 1EaStCHEM School of Chemistry, The University of Edinburgh David Brewster Road Edinburgh EH9 3FJ UK michael.ingleson@edinburgh.ac.uk.

Chemical Science
|April 10, 2023
PubMed
Summary

This study introduces a metal-free C-H borylation method using boron tribromide (BBr₃) to create borenium cations. This enables efficient reduction of amides to amines and synthesis of valuable borylated compounds and polycyclic aromatic hydrocarbons.

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

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Related Experiment Videos

Last Updated: Aug 3, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate

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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis

Published on: February 16, 2020

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Catalysis

Background:

  • Amide functional groups are common in organic molecules.
  • C-H activation and borylation are key transformations in organic synthesis.
  • Accessing complex borylated compounds often requires multi-step or metal-catalyzed procedures.

Purpose of the Study:

  • To develop a novel, metal-free method for C-H borylation directed by amide groups.
  • To enable subsequent reduction of the borylated amide to an amine.
  • To synthesize valuable borylated intermediates and novel polycyclic aromatic hydrocarbons (PAHs).

Main Methods:

  • Amide-directed C-H borylation using boron tribromide (BBr₃).
  • Formation of Lewis acidic borenium cations.
  • Reduction of the amide carbonyl to an amine using hydrosilanes.
  • Sequential one-pot borylation-reduction processes.
  • Hydrolysis to yield arylboronic acids or esters.

Main Results:

  • Efficient C-H borylation of amides, forming borenium cations.
  • Successful reduction of amides to amines via the borenium intermediate.
  • One-pot synthesis of ortho-borylated phenols and other functionalized arenes.
  • Synthesis of N-octyl-1-BPin-carbazole and novel B,N-polycyclic aromatic hydrocarbons (PAHs).
  • Demonstrated tolerance for variations in boron and amide substituents.

Conclusions:

  • A versatile, metal-free C-H borylation-reduction strategy has been established.
  • This method provides straightforward access to synthetically challenging borylated molecules and B,N-PAHs.
  • The developed methodology expands the toolbox for metal-free borylation and synthesis of functional organic materials.