Related Experiment Video
Updated: Jul 28, 2026

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
Palladium-catalysed cross-coupling reactions in supercritical carbon dioxide
T R Early1, R S Gordon, M A Carroll
1Melville Laboratory for Polymer Synthesis, Department of Chemistry, University of Cambridge, Pembroke Street, Cambridge, UK CB2 3RA.
Heck and Suzuki reactions were successfully performed in supercritical carbon dioxide, achieving good yields. This green chemistry approach utilizes palladium acetate and tri-tert-butylphosphine with various substrates.
Area of Science:
- Organic Chemistry
- Green Chemistry
- Catalysis
Background:
- Palladium-catalyzed cross-coupling reactions like Heck and Suzuki are vital in organic synthesis.
- Supercritical carbon dioxide (scCO2) offers an environmentally benign reaction medium with tunable properties.
- Developing efficient catalytic systems for reactions in scCO2 is crucial for sustainable chemistry.
Purpose of the Study:
- To investigate the efficacy of Heck and Suzuki reactions in supercritical carbon dioxide.
- To evaluate the performance of palladium acetate and tri-tert-butylphosphine as catalysts in scCO2.
- To assess the compatibility of both free and polymer-tethered substrates in this reaction system.
Main Methods:
- Utilizing supercritical carbon dioxide as a reaction solvent.
- Employing palladium acetate as the palladium source.
- Using tri-tert-butylphosphine as a ligand.
- Performing Heck and Suzuki cross-coupling reactions with diverse substrates.
Main Results:
- Heck and Suzuki reactions proceeded in good yields.
- The catalytic system demonstrated effectiveness with both free and polymer-tethered substrates.
- Supercritical carbon dioxide proved to be a viable and efficient medium for these transformations.
Conclusions:
- Supercritical carbon dioxide is a suitable and effective medium for palladium-catalyzed Heck and Suzuki reactions.
- The combination of palladium acetate and tri-tert-butylphosphine efficiently catalyzes these reactions in scCO2.
- This methodology offers a greener alternative for important carbon-carbon bond-forming reactions.
More Related Videos
Related Concept Videos
β-Dicarbonyl Compounds via Crossed Claisen Condensations
Cycloaddition Reactions: Overview
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Crossed Aldol Reactions: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
![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)
