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Related Concept Videos

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
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
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

3.0K
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...
3.0K
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

3.7K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
3.7K
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H

5.7K
All meta-directing substituents are deactivating groups. These substituents withdraw electrons from the aromatic ring, making the ring less reactive toward electrophilic substitution. For example, the nitration of nitrobenzene is 100,000 times slower than that of benzene because of the deactivating effect of the nitro group. The first step in an electrophilic aromatic substitution is the addition of an electrophile to form a resonance-stabilized carbocation. The energy diagrams for...
5.7K
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

3.1K
The Knoevenagel condensation is an aldol-type reaction involving the condensation of aldehydes or ketones with active methylene compounds such as β-diesters to produce substituted olefins.
3.1K

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Related Experiment Video

Updated: Aug 16, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Direct Deaminative Functionalization.

Balu D Dherange1, Mingbin Yuan2, Christopher B Kelly3

  • 1Department of Chemistry, University of Chicago, Chicago, Illinois 60637, United States.

Journal of the American Chemical Society
|December 22, 2022
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method for converting amines into various functional groups like halides and alcohols. This deaminative radical process offers a versatile tool for complex molecule synthesis.

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Area of Science:

  • Organic Synthesis
  • Catalysis
  • Radical Chemistry

Background:

  • Selective functional group interconversions are crucial in organic synthesis.
  • Amines are abundant but challenging to functionalize directly.
  • Existing methods for amine transformation are limited.

Purpose of the Study:

  • To develop a novel method for direct amine functionalization.
  • To enable the conversion of amines into diverse functional groups.
  • To overcome limitations in current amine interconversion strategies.

Main Methods:

  • Utilized an anomeric amide reagent for deaminative radical formation.
  • Employed experimental and computational mechanistic studies.
  • Applied high-throughput parallel synthesis for library evaluation.

Main Results:

  • Achieved direct conversion of amines to bromides, chlorides, iodides, phosphates, thioethers, and alcohols.
  • Demonstrated the importance of outcompeting H-atom transfer and generating productive radicals.
  • Successfully applied the method in one-pot diversification protocols.

Conclusions:

  • The developed deaminative carbon-centered radical formation is a powerful tool for amine functionalization.
  • This approach expands the synthetic utility of amines in complex molecular settings.
  • The method facilitates efficient library diversification and the development of new synthetic protocols.