Related Experiment Video
Updated: Jul 17, 2026

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
Published on: October 18, 2019
Silica-supported sodium sulfonate with ionic liquid: a neutral catalyst system for Michael reactions of indoles in
Yanlong Gu1, Chikako Ogawa, Shū Kobayashi
1Graduate School of Pharmaceutical Sciences, The University of Tokyo, The HFRE Division, ERATO, Japan Science and Technology Agency, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Abstract:
A neutral catalytic system for Michael reactions of indoles has been developed by combining silica-supported benzenesulfonic acid sodium salt with hydrophobic ionic liquid in water. An efficient hydrophobic environment could be created on the surface of the silica-sodium material under the conditions. Various indole derivatives and alpha,beta-unsaturated carbonyl compounds including some acid-labile substrates were successfully applied to this system with water as the sole solvent to afford the desired Michael adducts in high yields. [structure: see text].
Related Concept Videos
Preparation and Reactions of Sulfides
Conjugate Addition of Enolates: Michael Addition
Nucleophilic Aromatic Substitution of Aryldiazonium Salts: Aromatic SN1
In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo, or cyano...
Nucleophilic Substitution Reactions
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...
Electrophilic Aromatic Substitution: Sulfonation of Benzene
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
