The Catalytic Friedel–Crafts Acylation Reaction Starting from Aromatic Compounds and Free Carboxylic Acids (or Their Trimethylsilyl Esters) by Promotion of Silicon(IV) Cationic Species via Mixed Anhydrides
- 1 December 1993
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 66 (12) , 3729-3734
- https://doi.org/10.1246/bcsj.66.3729
Abstract
In the presence of active cationic species generated from silicon(IV) chloride and silver perchlorate, carboxylic acids or their trimethylsilyl esters react with p-trifluoromethylbenzoic anhydride to form corresponding mixed anhydrides in situ. Then the catalytic Friedel–Crafts acylation reaction between initially formed mixed anhydrides and coexisted aromatic compounds smoothly proceeds at room temperature to afford the corresponding aromatic ketones in high yields. The above two sequential reactions are effectively promoted by the active silicon(IV) catalyst under mild conditions.Keywords
This publication has 9 references indexed in Scilit:
- Organic reactions catalyzed by solid superacids. 5. Perfluorinated sulfonic acid resin (Nafion-H) catalyzed intramolecular Friedel-Crafts acylationThe Journal of Organic Chemistry, 1991
- Trimethylsilyl polyphosphate for intramolecular Friedel-Crafts cyclizationsThe Journal of Organic Chemistry, 1989
- Silica-Supported Heteropoly Acid Catalyst for Liquid-Phase Friedel–Crafts ReactionsBulletin of the Chemical Society of Japan, 1989
- Racemisierungsfreie Eisen(III)‐chlorid‐katalysierte Acylierung von Aromaten mit N ‐Phthaloyl‐α‐aminosäurechloridenEuropean Journal of Inorganic Chemistry, 1988
- Intramolekulare Friedel‐Crafts‐Acylierung von N ‐Phthaloyl‐substitutierten Aryl‐ und HomophenylalanylchloridenEuropean Journal of Inorganic Chemistry, 1988
- Friedel-Crafts acylation of toluene and p-xylene with carboxylic acids catalyzed by zeolitesThe Journal of Organic Chemistry, 1986
- Methanesulfonic acid catalyzed cyclization of 3-arylpropanoic and 4-arylbutanoic acids to 1-indanones and 1-tetralonesThe Journal of Organic Chemistry, 1981
- Catalysis by 12-Heteropolymolybdic Acid. II. Friedel-Crafts-type Reaction of Aromatic CompoundsBulletin of the Chemical Society of Japan, 1980
- Catalytic Friedel‐Crafts Acylation of Aromatic CompoundsAngewandte Chemie International Edition in English, 1972