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Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation01:01

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Benzaldehyde, like formaldehyde, lacks an α hydrogen and cannot enolize to form an enolate. Hence, the reaction of benzaldehyde with a ketone in the presence of an aqueous base forms a single crossed product. This reaction is referred to as Claisen–Schmidt condensation.
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
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Preparation of Alcohols via Substitution Reactions01:38

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Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group.  The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2,  depending on the nature of carbon attached to the halide.
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Aldehydes and ketones are prepared from alcohols, alkenes, and alkynes via different reaction pathways. Alcohols are the most commonly used substrates for synthesizing aldehydes and ketones. The conversion of alcohol to aldehyde, which involves the oxidation process, depends on the class of the alcohol used and the strength of the oxidizing agent. For instance, primary alcohol will form an aldehyde when treated with a weak oxidizing agent; however, it gets over-oxidized to a carboxylic acid in...
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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...
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α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.
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Machine Learning-Driven Automated Synthesis of Polysubstituted Gentisaldehydes.

Jiaolong Meng1, Hongbin Yang2, Chengliang Li1

  • 1Hainan Institute of East China Normal University, Shanghai Key Laboratory of Green Chemistry and Chemical Processes, State Key Laboratory of Petroleum Molecular & Process Engineering, School of Chemistry and Molecular Engineering, East China Normal University, 3663 North Zhongshan Road, Shanghai, 200062, P.R. China.

Angewandte Chemie (International Ed. in English)
|October 18, 2025
PubMed
Summary

Computer-aided synthesis planning developed a new method for making polysubstituted gentisaldehydes (PGAs). This automated flow system streamlines synthesis, offering industrial potential for pharmaceutical applications.

Keywords:
1,5‐Hydrogen atom transferAutomated flow chemistryDiradical intermediatesMachine‐learning‐drivenPolysubstituted gentisaldehydes

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Area of Science:

  • Organic Chemistry
  • Computational Chemistry
  • Chemical Engineering

Background:

  • Gentisaldehyde is a key pharmaceutical building block.
  • Current synthesis methods are inefficient, costly, and time-consuming.
  • A novel retrosynthetic approach is needed to improve efficiency and reduce synthetic redundancy.

Purpose of the Study:

  • To develop a disruptive retrosynthetic method for polysubstituted gentisaldehydes (PGAs).
  • To establish an automated synthesis process for efficient PGA library construction.
  • To elucidate the reaction mechanism using computational studies.

Main Methods:

  • Computer-Aided Synthesis Planning (CASP) algorithms for route deduction.
  • Automated flow system for streamlined synthesis.
  • Density Functional Theory (DFT) for mechanistic studies.

Main Results:

  • Systematic deduction of synthetic routes toward PGAs.
  • Development of an automated flow system for selective 6-endo cyclization.
  • Identification of diradical intermediates and a 1,5-hydrogen atom transfer mechanism.
  • Rapid, gram-scale library construction of PGAs.

Conclusions:

  • The study presents an innovative model for integrated molecule library construction.
  • The developed method enhances ring-formation capability and reduces synthetic redundancy.
  • The findings highlight the industrial potential for scalable PGA synthesis and application.