Related Experiment Video
Updated: Jun 6, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
Published on: November 30, 2022
Silver-Catalyzed Thio-Claisen Rearrangement of Aryl Sulfoxides with AIBN
1Key Laboratory of Precision and Intelligent Chemistry and Department of Chemistry, University of Science and Technology of China, Hefei, 230026, P. R. China.
Abstract:
The Pummerer reaction represents a well-known transformation of sulfoxides. Mechanistically, this reaction is initiated by the generation of the thionium ion, whereas forming such intermediates typically requires the use of a stoichiometric amount of activating reagent. In this regard, we report the activator-free Pummerer-type transformation, a silver-catalyzed thio-Claisen rearrangement of aryl sulfoxides with AIBN. Facilitated by silver catalyst, AIBN is transformed into highly reactive ketenimine in situ, which directly captures the sulfoxides to generate thionium ion intermediates.
More Related Videos
12:27Synthesis of Hypervalent Iodonium Alkynyl Triflates for the Application of Generating Cyanocarbenes
Published on: September 8, 2013
09:54Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
Published on: September 12, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
Preparation and Reactions of Sulfides
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between...
Nucleophilic Aromatic Substitution: Elimination–Addition