Related Experiment Video
Updated: Jul 2, 2026

The Synthesis, Characterization and Reactivity of a Series of Ruthenium N-triphosPh Complexes
Published on: April 10, 2015
Ruthenium-catalyzed carbonylative cycloaddition reactions involving carbonyl and imino groups as assembling units
1Department of Applied Chemistry, Faculty of Engineering, Osaka University, Suita, Osaka 565-0871, Japan.
Abstract:
This paper describes carbonylative cycloaddition reactions catalyzed by Ru3(CO)12. Ru3(CO)12 was found to catalyze an intramolecular Pauson-Khand-type reaction. Carbonylative cycloaddition reactions involving a carbonyl group in aldehydes, ketones, and esters as a two-atom assembling unit were also achieved in the presence of Ru3(CO)12 as the catalyst. The reaction of 5-hexyn-1-al and 6-heptyn-1-al derivatives with CO in the presence of Ru3(CO)12 resulted in cyclocarbonylation from which bicyclic alpha, beta-unsaturated lactones were obtained. Intermolecular [2 + 2 + 1] carbonylative cycloaddition of alkenes, ketones, and CO was also catalyzed by Ru3(CO)12 as the catalyst to give saturated gamma-lactone derivatives. Simple ketones were not applicable, but ketones having a C==O or C==N group at the alpha-position served as a good substrate. These reactions could be extended to carbonylative cycloaddition of the corresponding imines leading to gamma-butyrolactam derivatives. The [4 + 1] carbonylative addition of alpha,beta-unsaturated imines leading to unsaturated gamma-lactams was achieved with Ru3(CO)12.
More Related Videos
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
06:46Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Cycloaddition Reactions: Overview
Olefin Metathesis Polymerization: Overview
Ruthenium-based Grubbs catalyst is the most commonly used catalyst for olefin metathesis polymerization. Grubbs catalyst consists of a...
Cycloaddition Reactions: MO Requirements for Thermal Activation
Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview
Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...