Related Experiment Video
Updated: May 12, 2025

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Gold-Catalyzed Deallylative C-S Cross-Coupling Reactions
Prafulla Bera1, Tanmayee Nanda1, Nayan A Barhate1
1Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri 462 066, India.
This study introduces a novel gold-catalyzed deallylative C-S cross-coupling using a ligand-enabled Au(I)/Au(III) redox cycle. Allyl phenyl sulfide acts as a sulfur surrogate, preventing catalyst deactivation and enabling efficient coupling reactions.
Area of Science:
- Organometallic Chemistry
- Catalysis
- Synthetic Organic Chemistry
Background:
- Gold catalysis is crucial for C-S bond formation.
- Catalyst deactivation via gold-sulfur bond formation is a significant challenge.
Purpose of the Study:
- To develop a gold-catalyzed deallylative C-S cross-coupling reaction.
- To overcome catalyst deactivation in gold-catalyzed C-S coupling.
Main Methods:
- Ligand-enabled Au(I)/Au(III) redox catalysis.
- Utilizing allyl phenyl sulfide as a sulfur surrogate.
- Mechanistic studies including 31P NMR, mass analysis, and computational modeling.
Main Results:
- Successful deallylative C-S cross-coupling reaction.
- Allyl phenyl sulfide facilitates a dynamic equilibrium, preventing gold catalyst quenching.
- Detailed mechanistic insights were obtained.
Conclusions:
- The developed method offers an efficient approach to C-S cross-coupling.
- The use of allyl phenyl sulfide is key to overcoming catalyst deactivation.
- The study provides a robust understanding of the reaction mechanism.
More Related Videos
06:34Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
Published on: June 20, 2014
11:44Mizoroki-Heck Cross-coupling Reactions Catalyzed by Dichloro{bis[1,1',1''-phosphinetriyltripiperidine]}palladium Under Mild Reaction Conditions
Published on: March 20, 2014
Related Concept Videos
Preparation and Reactions of Sulfides
Cycloaddition Reactions: Overview
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction
Crossed Aldol Reactions: Overview
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview
β-Dicarbonyl Compounds via Crossed Claisen Condensations