Friedel-Crafts Alkylation

This Lewis acid-catalyzed electrophilic aromatic substitution allows the synthesis of alkylated products via the reaction of arenes with alkyl halides or alkenes. Since alkyl substituents activate the arene substrate, polyalkylation may occur. A valuable, two-step alternative is Friedel-Crafts Acylation followed by a carbonyl reduction.

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Mechanism of the Friedel-Crafts Alkylation

Using alkenes :

Recent Literature

Iron Oxide Nanoparticles Grown on Carboxy-Functionalized Graphite: An Efficient Reusable Catalyst for Alkylation of Arenes
V. Rajpara, S. Banerjee, G. Sereda, Synthesis, 2010, 2835-2840.

Dicationic Electrophiles from Olefinic Amines in Superacid
Y. Zhang, A. McElrea, G. V. Sanchez, D. Do, A. Gomez, S. L . Aguirre, R. Rendy, D. A. Klumpp, J. Org. Chem., 2003, 68, 5119-5122.

Conversion of Aryl Aldehydes to Benzyl Iodides and Diarylmethanes by H₃PO₃/I₂
F. Lv, J. Xiao, J. Xiang, F. Guo, Z.-L. Tang, L.-B. Han, J. Org. Chem., 2021, 86, 3081-3088.

Benzylic Phosphates in Friedel-Crafts Reactions with Activated and Unactivated Arenes: Access to Polyarylated Alkanes
G. Pallikonda, M. Chakravarty, J. Org. Chem., 2016, 81, 2135-2142.

Samarium Triflate-Catalyzed Halogen-Promoted Friedel-Crafts Alkylation with Alkenes
S. Haira, B. Maji, S. Bar, Org. Lett., 2007, 9, 2783-2786.

Dramatic Enhancement of Catalytic Activity in an Ionic Liquid: Highly Practical Friedel-Crafts Alkenylation of Arenes with Alkynes Catalyzed by Metal Triflates
C. E. Song, D.-U. Jung, S. Y. Choung, E. J. Roh, S.-G. Lee, Angew. Chem. Int. Ed., 2004, 43, 6183-6185.

MA-Silica Gel Catalyzed Propargylation of Aromatic Compounds with Arylpropargyl Alcohols under Solvent-Free Conditions
P. Srihari, J. S. S. Reddy, S. S. Mandal, K. Satyanarayana, J. S. Yadav, Synthesis, 2008, 1853-1860.

Unexpected Formation of 3-Substituted 1,2,3,4-Tetrahydroisoquinolines during Tosylation of N,N-dibenzylaminols
S. Chandrasekhar, P. K. Mohanty, K. Harikishan, P. K. Sasmal, Org. Lett., 1999, 1, 877-879.

Silyl Cyanopalladate-Catalyzed Friedel-Crafts-Type Cyclization Affording 3-Aryloxindole Derivatives
H. Ece, Y. Tange, T. Yurino, T. Ohkuma, Synlett, 2021, 32, 935-939.

Iron-Catalyzed Synthesis of Tetrahydronaphthalenes via 3,4-Dihydro-2H-pyran Intermediates
R. B. Watson, C. S. Schindler Org. Lett., 2018, 20, 68-71.

Metal-Free Tandem Friedel–Crafts/Lactonization Reaction to Benzofuranones Bearing a Quaternary Center at C3 Position
L. Chen, F. Zhou, T.-D. Shi, J. Zhou, J. Org. Chem., 2012, 77, 4354-4362.

Addition of Arylboronic Acids to Arylpropargyl Alcohols en Route to Indenes and Quinolines
J. Panteleev, R. Y. Huang, E. K. J. Lui, M. Lautens, Org. Lett., 2011, 13, 5314-5317.

Conversion of 2-Alkylcinnamaldehydes to 2-Alkylindanones via a Catalytic Intramolecular Friedel-Crafts Reaction
G. B. Womack, J. G. Angeles, V. E. Fanelli, C. A. Heyer, J. Org. Chem., 2007, 72, 7046-7049.