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Related Concept Videos

Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

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.
meta-Directing Deactivators: –NO2, –CN, –CHO, –⁠CO2R, –COR, –CO2H01:13

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

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 the...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

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...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

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 amide...
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

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...
Aldol Condensation with β-Diesters: Knoevenagel Condensation01:27

Aldol Condensation with β-Diesters: Knoevenagel Condensation

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.

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Updated: May 28, 2026

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
09:45

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

Published on: April 27, 2017

Direct deaminative functionalization.

Zhangkai Cui1, Hongjian Lu1,2

  • 1State Key Laboratory of Coordination Chemistry, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, Jiangsu 210093, China. hongjianlu@nju.edu.cn.

Chemical Society Reviews
|May 27, 2026
PubMed
Summary
This summary is machine-generated.

Direct deaminative functionalization transforms amines from static endpoints into reactive handles. This strategy efficiently converts carbon-nitrogen bonds into carbon-carbon and carbon-heteroatom linkages for molecular editing.

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Last Updated: May 28, 2026

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

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Amines are fundamental building blocks in nature and synthetic molecules.
  • Traditionally viewed as stable endpoints, amines offer untapped potential for synthetic manipulation.
  • Existing synthetic methods often require pre-functionalization, limiting amine utility.

Purpose of the Study:

  • To present a unified framework for direct deaminative functionalization of amines.
  • To systematically review advances in converting C-N bonds into C-C and C-heteroatom linkages.
  • To highlight the role of activation platforms in late-stage functionalization and molecular diversification.

Main Methods:

  • A bond-centric organization of existing literature on deaminative functionalization.
  • Categorization of methods based on the specific bond formed (e.g., C-C, C-N, C-O, C-S).
  • Analysis of various activation platforms enabling direct C-N bond cleavage.

Main Results:

  • Established a comprehensive overview of direct deaminative functionalization strategies.
  • Demonstrated the step-economic nature of converting C-N bonds.
  • Showcased the versatility in forming diverse C-C and C-heteroatom bonds.
  • Highlighted the utility of different activation platforms for late-stage functionalization.

Conclusions:

  • Direct deaminative functionalization represents a paradigm shift in amine chemistry.
  • This approach offers a powerful and efficient route for molecular editing and diversification.
  • The unified framework facilitates understanding and development of new synthetic methodologies.