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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.8K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic halogen to form a...
3.8K
Base-Promoted α-Halogenation of Aldehydes and Ketones00:51

Base-Promoted α-Halogenation of Aldehydes and Ketones

3.4K
α-Halogenation of aldehydes and ketones is a reaction involving the substitution of α hydrogens with halogens in the presence of a base.  The reaction begins with the abstraction of  α hydrogen by the base to produce a nucleophilic enolate ion. This intermediate undergoes a subsequent nucleophilic substitution with the halogen to produce a monohalogenated carbonyl compound. If the starting substrate has more than one α hydrogen, it is difficult to stop the reaction...
3.4K
Aryldiazonium Salts to Azo Dyes: Diazo Coupling01:11

Aryldiazonium Salts to Azo Dyes: Diazo Coupling

2.9K
The reaction of weakly electrophilic aryldiazonium (also called arenediazonium) salts with highly activated aromatic compounds leads to the formation of products with an —N=N— link, called an azo linkage. This reaction, presented in Figure 1, is known as diazo coupling and occurs without the loss of the nitrogen atoms of the aryldiazonium salt. Highly activated aromatic compounds such as phenols or arylamines favor the diazo coupling reaction. The coupling generally occurs at the...
2.9K
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

2.8K
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...
2.8K
α-Halogenation of Carboxylic Acid Derivatives: Overview01:14

α-Halogenation of Carboxylic Acid Derivatives: Overview

3.3K
Unlike aldehydes and ketones, carboxylic acids do not readily participate in α halogenation reactions via enols or enolate intermediates. However, α-halogenated acids are obtained through other methods. One of the approaches is the Hell–Volhard–Zelinsky (HVZ) reaction, wherein the carboxylic acid is treated with halogen in the presence of PBr3. It involves the conversion of acid to acid halide, which exists in equilibrium with its enol form. The enol attacks the...
3.3K
Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.1K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.1K

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Related Experiment Video

Updated: Jul 9, 2025

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
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Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

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Visible-light-enabled cascade cross-dehydrogenative-coupling/cyclization to construct α-chromone substituted α-amino

Zhi-Qiang Zhu1, Jia-Yu Hu1, Zong-Bo Xie1

  • 1Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry and Materials Science, East China University of Technology, Nanchang, 330013, China. zhuzq@ecut.edu.cn.

Chemical Communications (Cambridge, England)
|November 30, 2023
PubMed
Summary

A novel organophotocatalytic method enables the synthesis of α-chromone substituted α-amino acid derivatives. This efficient cascade reaction couples o-hydroxyarylenaminones with amino acid derivatives under visible light.

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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Medicinal Chemistry

Background:

  • Chromone derivatives are important scaffolds in medicinal chemistry.
  • Efficient synthesis of α-chromone substituted α-amino acids is challenging.

Purpose of the Study:

  • To develop a novel organophotocatalytic cascade reaction for synthesizing α-chromone substituted α-amino acid derivatives.
  • To explore the scope and efficiency of this new synthetic route.

Main Methods:

  • Organophotocatalytic cascade cross-dehydrogenative-coupling/cyclization reaction.
  • Visible-light-promoted oxidation of α-amino acid derivatives.
  • Mannich reaction and intramolecular nucleophilic cyclization under acidic conditions.

Main Results:

  • Successfully synthesized various α-chromone substituted α-amino acid derivatives.
  • Achieved good to excellent yields for the target compounds.
  • Demonstrated a wide reaction scope with different N-arylglycine esters, amides, and dipeptides.

Conclusions:

  • The developed method provides an efficient and mild route to α-chromone substituted α-amino acid derivatives.
  • This approach offers a simple operation and broad applicability.
  • Potential applications in the synthesis of bioactive molecules.