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Updated: Jun 25, 2026

A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
Catalytic formal Homo-Nazarov cyclization.
Filippo De Simone1, Julien Andrès, Riccardo Torosantucci
1Laboratory of Catalysis and Organic Synthesis Ecole Polytechnique Fédérale de Lausanne EPFL SB ISIC LCSO, BCH 4306, 1015 Lausanne, Switzerland.
Researchers developed the first catalytic method for vinyl-cyclopropyl ketone cyclization, a formal homo-Nazarov reaction. This new approach efficiently synthesizes heterocyclic and carbocyclic compounds from activated cyclopropanes under mild conditions.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- The Nazarov cyclization is a powerful tool for carbocycle synthesis.
- Homo-Nazarov reactions offer alternative pathways to complex molecular scaffolds.
- Catalytic methods for cyclopropane functionalization are highly sought after in organic synthesis.
Purpose of the Study:
- To report the first catalytic method for the cyclization of vinyl-cyclopropyl ketones.
- To develop a novel synthetic route for heterocyclic and carbocyclic compounds.
- To explore the mechanism of this new cyclization reaction.
Main Methods:
- Utilizing Brønsted acid catalysts.
- Employing activated cyclopropanes as starting materials.
- Investigating the reaction mechanism through preliminary studies.
Main Results:
- Successful cyclization of vinyl-cyclopropyl ketones was achieved.
- A range of heterocyclic and carbocyclic compounds were synthesized.
- The reaction proceeds under mild conditions.
- Preliminary mechanistic studies suggest a stepwise process.
Conclusions:
- A novel and efficient catalytic method for vinyl-cyclopropyl ketone cyclization (formal homo-Nazarov reaction) has been established.
- This methodology provides access to diverse heterocyclic and carbocyclic structures.
- The reaction offers a mild and effective route for synthesizing valuable organic compounds.
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