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
M. H. Sarvari, H. Sharghi, Synthesis, 2004, 2165-2168.
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.
A General Method for Acylation of Indoles at the 3-Position with Acyl Chlorides in the Presence of Dialkylaluminum Chloride
T. Okauchi, M. Itonaga, T. Minami, T. Owa, K. Kitoh, H. Yoshino, Org. Lett., 2000, 2, 1485-1487.
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.