Wednesday, April 22, 2020

FRIEDEL-CRAFTS ACYLATION

Friedel-Crafts Acylation





This electrophilic aromatic substitution allows the synthesis of monoacylated products from the reaction between arenes and acyl chlorides or anhydrides. The products are deactivated, and do not undergo a second substitution. Normally, a stoichiometric amount of the Lewis acid catalyst is required, because both the substrate and the product form complexes.

The Friedel-Crafts Alkylation may give polyalkylated products, so the Friedel-Crafts Acylation is a valuable alternative. The acylated products may easily be converted to the corresponding alkanes via Clemmensen Reduction or Wolff-Kishner Reduction.

Mechanism of the Friedel-Crafts Acylation



Recent Literature




Reactions on a Solid Surface. A Simple, Economical and Efficient Friedel-Crafts Acylation Reaction over Zinc Oxide (ZnO) as a New Catalyst




Mild, Efficient Friedel-Crafts Acylations from Carboxylic Acids Using Cyanuric Chloride and AlCl3




"Greener" Friedel-Crafts Acylations: A Metal- and Halogen-Free Methodology




Simple and Improved Procedure for the Regioselective Acylation of Aromatic Ethers with Carboxylic Acids on the Surface of Graphite in the Presence of Methanesulfonic Acid




An intermolecular Friedel-Crafts acylation in hexafluoro-2-propanol provides aryl and heteroaryl ketones at room temperature without any additional reagents.




Zinc Mediated Friedel-Crafts Acylation in Solvent-Free Conditions under Microwave Irradiation




Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions




Esters as Acylating Reagent in a Friedel-Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane




In(III)-Mediated Chemoselective Dehydrogenative Interaction of ClMe2SiH with Carboxylic Acids: Direct Chemo- and Regioselective Friedel-Crafts Acylation of Aromatic Ethers




Intramolecular Friedel-Crafts Acylation Reaction Promoted by 1,1,1,3,3,3-Hexafluoro-2-propanol




Trifluoromethanesulfonic acid catalyzed Friedel-Crafts acylation of aromatics with β-lactams




Reliable and Versatile Synthesis of 2-Aryl-Substituted Cinnamic Acid Esters




Titanium(IV) Chloride-Mediated Ortho-Acylation of Phenols and Naphthols




Efficient Synthesis of β-Chlorovinylketones from Acetylene in Chloroaluminate Ionic Liquids




A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel-Crafts Acylation of Vinyl Chlorides




Efficient, One-Pot, BF3·OEt2-Mediated Synthesis of Substituted N-Aryl Lactams




Synthesis of Indazolones via Friedel-Crafts Cyclization of Blocked (Masked) N-Isocyanates




Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones

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