Related Experiment Video
Updated: Jul 20, 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
Ruthenium-catalyzed hydrative cyclization of 1,5-enynes
Yiyun Chen1, Douglas M Ho, Chulbom Lee
1Department of Chemistry, Princeton University, Princeton, New Jersey, 08544-1009, USA.
Abstract:
A ruthenium-catalyzed hydrative cyclization of enynes has been developed. The reaction converts a range of 1,5-enynes bearing terminal alkyne and Michael acceptor moieties into cyclopentanone derivatives. From extensive catalyst screening experiments, a trinuclear ruthenium complex, [Ru3(dppm)3Cl5]PF6, has been identified to be an effective catalyst in mediating the 1,1-difunctionalization of alkynes. It is proposed that this novel umpolung reaction proceeds through the formation of a ruthenium vinylidene, anti-Markovnikov hydration, and intramolecular Michael addition of an acyl ruthenium to the alkene.
More Related Videos
Related Concept Videos
Catalysis
Formation of Halohydrin from Alkenes
Acid-Catalyzed Hydration of Alkenes
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
Aldehydes and Ketones with Water: Hydrate Formation
The formation of hydrates is a reversible reaction. Hydrate formation is influenced by steric and electronic factors accompanying the alkyl substituents on the carbonyl group: The rate of hydrate formation increases with a decrease in the number of alkyl groups attached to the carbonyl carbon. Hence,...
Catalysis

