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Updated: Jul 10, 2026
![Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F51444.jpg&w=3840&q=50)
Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-(phosphinetriyl)tripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Polarizing the Nazarov cyclization: efficient catalysis under mild conditions.
Wei He1, Xiufeng Sun, Alison J Frontier
1Department of Chemistry, University of Rochester, Rochester, NY 14627, USA.
Substituted divinyl ketones efficiently undergo Nazarov cyclization using copper triflate catalysis. This reaction yields a single cyclopentenone isomer, with efficiency depending on substituent electronic effects.
Area of Science:
- Organic Chemistry
- Catalysis
- Synthetic Methodology
Background:
- The Nazarov cyclization is a key reaction for synthesizing cyclopentenones.
- Understanding substituent effects is crucial for controlling regio- and stereoselectivity.
Purpose of the Study:
- To investigate the Nazarov cyclization of substituted divinyl ketones.
- To explore the role of electronic polarization in reaction efficiency and selectivity.
Main Methods:
- Utilized catalytic copper triflate (2 mol %) for the Nazarov cyclization.
- Studied alpha-carbomethoxy divinyl ketones as substrates.
Main Results:
- Achieved efficient Nazarov cyclization of alpha-carbomethoxy divinyl ketones.
- Obtained a single cyclopentenone regio- and stereoisomer.
- Correlated cyclization efficiency with substituent polarization of the cationic intermediate's pi-system.
Conclusions:
- Catalytic copper triflate is effective for the Nazarov cyclization of these substrates.
- Substituent electronic properties significantly influence the outcome of the Nazarov cyclization.
- The findings provide insights into controlling cyclopentenone synthesis.
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