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
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
Reactions on a Solid Surface. A Simple, Economical and Efficient Friedel-Crafts Acylation Reaction over Zinc Oxide (ZnO) as a New Catalyst
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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
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An intermolecular Friedel-Crafts acylation in hexafluoro-2-propanol provides aryl and heteroaryl ketones at room temperature without any additional reagents.
R. H. Vekariya, J. Aubé, Org. Lett., 2016, 18, 3534-3537.
Aluminum dodecatungstophosphate (AlPW12O40) as a non-hygroscopic Lewis acid catalyst for the efficient Friedel-Crafts acylation of aromatic compounds under solvent-less conditions
H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Tetrahedron, 2004, 60, 10843-10850.
Esters as Acylating Reagent in a Friedel-Crafts Reaction: Indium Tribromide Catalyzed Acylation of Arenes Using Dimethylchlorosilane
Y. Nishimoto, S. A. Babu, M. Yasuda, A. Baba, J. Org. Chem., 2008, 73, 9465-9468.
In(III)-Mediated Chemoselective Dehydrogenative Interaction of ClMe2SiH with Carboxylic Acids: Direct Chemo- and Regioselective Friedel-Crafts Acylation of Aromatic Ethers
S. A. Babu, M. Yasuda, A. Baba, Org. Lett., 2007, 9, 405-408.
A General Method for the Synthesis of 3,5-Diarylcyclopentenones via Friedel-Crafts Acylation of Vinyl Chlorides
Y. Xu, M. McLaughlin, C.-y. Chen, R. A. Reamer, P. G. Dormer, I. W. Davies, J. Org. Chem., 2009, 74, 5100-5103.
Unified Approach to (Thio)chromenones via One-Pot Friedel-Crafts Acylation/Cyclization: Distinctive Mechanistic Pathways of β-Chlorovinyl Ketones
H. Y. Kim, E. Song, K. Oh, Org. Lett., 2017, 19, 312-315.