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Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine 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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Updated: Oct 29, 2025

Microscopic Visualization of Porous Nanographenes Synthesized through a Combination of Solution and On-Surface Chemistry

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Published on: March 4, 2021

Synthesis on inert surfaces.

Markus Lackinger¹

¹Deutsches Museum, Museumsinsel 1, 80538 München, Germany and Physics Department, Technische Universität München, James-Franck-Strasse 1, 85748 Garching, Germany. markus@lackinger.org.

Dalton Transactions (Cambridge, England : 2003)

|July 8, 2021

Summary

This summary is machine-generated.

Synthesizing robust covalent organic nanostructures on inert surfaces is challenging due to reactant desorption. New methods like photochemical coupling are needed for direct synthesis on insulating supports for electronic applications.

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Area of Science:

Materials Science
Organic Chemistry
Surface Science

Background:

Covalent organic nanostructures exhibit remarkable properties for electronic applications.
Current synthesis methods are limited to metal surfaces, requiring difficult post-synthetic transfers.
Insulating supports are necessary for direct integration into devices like field-effect transistors and sensors.

Purpose of the Study:

To explore direct synthesis of covalent organic nanostructures on inert surfaces.
To overcome challenges associated with carbon-carbon coupling on weakly interacting substrates.
To identify new strategies for fabricating nanostructures on insulating materials.

Main Methods:

Review of existing synthesis techniques for covalent organic nanostructures.
Analysis of the "desorption problem" in thermally activated coupling on inert surfaces.
Proposal of photochemical coupling and pre-activation of monomers as alternative strategies.

Main Results:

Carbon-carbon coupling remains largely unachieved on inert surfaces for nanostructure synthesis.
Thermally activated coupling is hindered by reactant desorption, exacerbated on inert supports.
Photochemical coupling and monomer pre-activation are identified as promising alternative approaches.

Conclusions:

Direct synthesis of covalent organic nanostructures on inert surfaces is crucial for electronic applications.
Novel synthetic paradigms are required to circumvent desorption issues on insulating materials.
Future research should focus on photochemical methods and monomer activation for on-demand nanostructure fabrication.